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3051 KiB

Open AccessProceeding Paper

Assessing the Strategic Preparation of Coordination Polymer Particles: A Computational Analysis of the Impact of Different Catechol-Based Ligands

by Matías Capurso, Gabriel Radivoy, Fabiana Nador and Viviana Dorn

Chem. Proc. 2023, 14(1), 1; https://doi.org/10.3390/ecsoc-27-16098 - 15 Nov 2023

Viewed by 319

Abstract

DFT calculations were applied to an iron/catechol derivative system to investigate their effect on the structure of CPPs as a function of (a) metal valence—Fe⁺² and Fe⁺³ in high- and low-spin states; (b) type of chelating groups in the catechol derivatives [...] Read more.

DFT calculations were applied to an iron/catechol derivative system to investigate their effect on the structure of CPPs as a function of (a) metal valence—Fe⁺² and Fe⁺³ in high- and low-spin states; (b) type of chelating groups in the catechol derivatives and their geometries; and (c) the aliphatic chain length between two chelating groups in a model polydentate ligand. The results indicate that catechol-pyridine and bis-catechol ligands, with Fe⁺³ salts, are promising combinations to synthesize CPPs. In addition, the inclusion of an aliphatic chain with four carbons between the chelating groups could enhance polymerization versus monomer formation. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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704 KiB

Open AccessProceeding Paper

Synthesis and Characterization of Hybrid Structures Based on Furan-2(3H)-ones and Chromen-4(4H)-ones—Potential Antibacterial Activity

by Ekaterina M. Arzyamova, Danila O. Tarasov and Alevtina Yu. Yegorova

Chem. Proc. 2023, 14(1), 2; https://doi.org/10.3390/ecsoc-27-16062 - 15 Nov 2023

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Abstract

One of the modern trends in medicinal chemistry is the design of multifunctional drugs with a wide spectrum of actions. The main approaches to the creation of such drugs are the construction of new biologically active substances containing two or more pharmacophore groups [...] Read more.

One of the modern trends in medicinal chemistry is the design of multifunctional drugs with a wide spectrum of actions. The main approaches to the creation of such drugs are the construction of new biologically active substances containing two or more pharmacophore groups in their structure or the introduction of an additional pharmacophore group into the molecule of a known drug. This work describes the synthesis of hybrid structures based on furan-2(3H)-ones and chromen-4(4H)-ones under the conditions of the Knoevenagel reaction. Various reaction conditions were screened. (E)-3-((2-oxo-5-arylfuran-3(2H)-ylidene)methyl)-4H-chromen-4-ones were obtained, and its structure was confirmed by ¹H and ¹³C NMR spectroscopy data. Based on NMR spectroscopy data, it was shown that the resulting compounds exist in the form of E-isomers. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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899 KiB

Open AccessProceeding Paper

Design, Synthesis and Structural Study of a Bisthiosemicarbazone Ligand Precursor of Metallosupramolecular Architectures

by Uxía Barreiro-Sisto, Isabel Velo-Heleno, Miguel Martínez-Calvo, Marcelino Maneiro and Sandra Fernández-Fariña

Chem. Proc. 2023, 14(1), 3; https://doi.org/10.3390/ecsoc-27-16087 - 15 Nov 2023

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Abstract

The increase in the investigation of different self-assembled architectures derived from thiosemicarbazone ligands can be attributed to the numerous functional metallosupramolecular architectures with practical applications that can be obtained. The potentially tetradentate organic bisthiosemicarbazone ligand H₂L possesses two flexible bidentate [...] Read more.

The increase in the investigation of different self-assembled architectures derived from thiosemicarbazone ligands can be attributed to the numerous functional metallosupramolecular architectures with practical applications that can be obtained. The potentially tetradentate organic bisthiosemicarbazone ligand H₂L possesses two flexible bidentate [NS] domains separated by a short and rigid spacer, which could stabilize several metal ions and thus different metallosupramolecular architectures. H₂L was prepared by the reaction between two equivalents of N-ethylhydrazinecarbothioamide and one equivalent of 1,1′,1″-(benzene-1,3,5-triyl)tris(ethan-1-one) and was fully studied using several techniques, including X-ray diffraction. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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3858 KiB

Open AccessProceeding Paper

Carbon Dots from Porphyridium cruentum Microalgae by High-Efficient Hydrothermal Approaches: Biocompatibility and Antioxidant Capabilities

by Inês Chouzende, Alexandra I. Costa, Patrícia D. Barata, Sónia Martins, Magda C. Semedo, Fernando M. H. Cardoso, Maria Luísa Lobo and José V. Prata

Chem. Proc. 2023, 14(1), 4; https://doi.org/10.3390/ecsoc-27-16074 - 15 Nov 2023

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Abstract

Fluorescent carbon dots (µAlgae-CDs) were successfully prepared from renewable Porphyridium cruentum biomass using a hydrothermal carbonization approach and ethylenediamine (ED) as a nitrogen additive. Structural and photophysical properties of the as-synthesized nanomaterials were evaluated using FTIR, UV-Vis, and fluorescence spectroscopies. The [...] Read more.

Fluorescent carbon dots (µAlgae-CDs) were successfully prepared from renewable Porphyridium cruentum biomass using a hydrothermal carbonization approach and ethylenediamine (ED) as a nitrogen additive. Structural and photophysical properties of the as-synthesized nanomaterials were evaluated using FTIR, UV-Vis, and fluorescence spectroscopies. The new µAlgae-CDs synthesized with a ratio of 0.16 of ED demonstrated good antioxidant properties by ABTS radical cation method and did not exhibit cytotoxicity against non-tumor Vero cells and tumor HeLa cells, showing potential application in bioimaging. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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658 KiB

Open AccessProceeding Paper

Synthesis of New Representatives of Push–Pull Enamines 5-Aryl-3-((dimethylamino)methylene)furan-2(3H)-Ones

by Alexandra S. Tikhomolova, Zhanna V. Mamleeva and Alevtina Yu. Yegorova

Chem. Proc. 2023, 14(1), 5; https://doi.org/10.3390/ecsoc-27-16056 - 15 Nov 2023

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Abstract

The conditions for the synthesis of dimethylaminomethylene derivatives were selected based on the interaction of arylfuran-2(3H)-ones and dimethylformamide dimethylacetal (DMA-DMF), proceeding through the methylene active unit of the furanone ring. The influence of the used solvent and the type of activation [...] Read more.

The conditions for the synthesis of dimethylaminomethylene derivatives were selected based on the interaction of arylfuran-2(3H)-ones and dimethylformamide dimethylacetal (DMA-DMF), proceeding through the methylene active unit of the furanone ring. The influence of the used solvent and the type of activation on the reaction rate and product yields was established. Using NMR spectroscopy and the one-dimensional version of NOESY1D with selective excitation of protons, it was revealed that these systems exist in the form of an E-configuration. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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2254 KiB

Open AccessProceeding Paper

Conformational Study of n,n’-(Alkane-1,n-diyl)bis(2-phenyl-3,5-dihydro-4H-imidazol-4-one)s with Different Spacer Length

by Anastasia A. Lobankova, Vyacheslav S. Grinev and Alevtina Yu. Yegorova

Chem. Proc. 2023, 14(1), 6; https://doi.org/10.3390/ecsoc-27-16053 - 15 Nov 2023

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Abstract

In this study, we investigated the conformational abilities of n,n’-(Alkanediyl)-bis(2-phenyl-3,5-dihydro-4H-imidazol-4-one)s (1) to gain insight into their biological potential as a platform for the generation of various QACs. Among the conformers of 1, due to the flexibility of the [...] Read more.

In this study, we investigated the conformational abilities of n,n’-(Alkanediyl)-bis(2-phenyl-3,5-dihydro-4H-imidazol-4-one)s (1) to gain insight into their biological potential as a platform for the generation of various QACs. Among the conformers of 1, due to the flexibility of the polymethylene fragment, the phenyl rings can take on different mutual arrangements, while there is a clear tendency for the formation of π–π interactions. From the point of view of the reactivity to alkylating agents, a preliminary conclusion can be drawn about the favorable mutual arrangement of imidazolone rings located at a sufficient distance to carry out both mono- and bisalkylation to obtain bis-QAC. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1518 KiB

Open AccessProceeding Paper

Synthesis of Symmetrical Monocarbonyl Analogs of Curcumin Containing a 2-Bromobenzylidene Moiety and Spectrophotometric Assessment of Their Reactivity with 2-(Dimethylamino)ethanthiol

by Zlatko Lozanovski, Ivana Todorovska, Katerina Dragarska and Jane Bogdanov

Chem. Proc. 2023, 14(1), 7; https://doi.org/10.3390/ecsoc-27-16084 - 15 Nov 2023

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Abstract

The cross-conjugated dienones containing the 1,5-diaryl-3-oxo-1,4-pentadienyl pharmacophore have diverse biological activities. These sometimes-called monocarbonyl analogs of curcumin (MACs) have especially pronounced biological activity when containing an electron-withdrawing group at the ortho-position of the benzene ring. Their biological activity most likely stems from a [...] Read more.

The cross-conjugated dienones containing the 1,5-diaryl-3-oxo-1,4-pentadienyl pharmacophore have diverse biological activities. These sometimes-called monocarbonyl analogs of curcumin (MACs) have especially pronounced biological activity when containing an electron-withdrawing group at the ortho-position of the benzene ring. Their biological activity most likely stems from a selective Michael reaction with thiols. It has been reported in the literature that certain MACs (in particular, EF24) react as electrophiles with glutathione and form bis adducts in vitro. Five MACs were prepared ((2E,5E)-2,5-bis(2-bromobenzylidene)cyclopentanone, (2BrCP), (2E,6E)-2,6-bis(2-bromobenzylidene)cyclohexanone (2BrCX, B2BrBC), (2E,6E)-2,6-bis(2-bromobenzylidene)- 4-tert-butyl-cyclohexanone (4tB2BrCX), (3E,5E)-3,5-bis(2-bromobenzylidene)-4-piperidone, (2Br4PIP) and (3E,5E)-3,5-bis(2-fluorobenzylidene)-4-piperidone, EF24), purified and characterized by spectroscopic means. The relative reactivity of these MACs towards 2-(dimethylamino)ethanethiol was assessed via a previously developed UV-Vis spectroscopic method and compared to EF24, which reacts readily in solution with thiols such as glutathione and cysteamine. All of the bis(2-bromobenzylidene) MACs react slower with 2-(dimethylamino)ethanethiol in 80:20 (v/v) acetonitrile/water compared to EF24. The relative reactivity of the analogs with 2-(dimethylamino)ethanethiol followed the order EF24 > 2Br4PIP > 2BrCX > 2BrCP > 4tB2BrCX. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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3 pages, 533 KiB

Open AccessProceeding Paper

The Reaction of 1,6-Diamino-4-aryl-2-oxo-1,2-dihydropyridine- 3,5-Dicarbonitriles with Certain Electrophilic Agents

by Alexei A. Dolganov, Alexandra R. Chikava and Victor V. Dotsenko

Chem. Proc. 2023, 14(1), 8; https://doi.org/10.3390/ecsoc-27-16081 - 06 Dec 2023

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Abstract

The reaction of 1,6-diamino-2-oxo-1,2-dihydropyridine-3,5-dicarbonitriles, which are easily available through the reaction of cyanoacetohydrazide with arylmethylene malononitriles, with ninhydrin leads to the formation of novel dihydroindeno[1,2-e]pyrido[1,2-b][1,2,4]triazines. Another active carbonyl compound, glyoxal, reacts with 1,6-diamino-2-oxo-1,2-dihydropyridine-3,5-dicarbonitriles under mild conditions to give functionalized 6-oxo-6H-pyrido[1,2-b][1,2,4]triazine-7,9-dicarbonitriles. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1157 KiB

Open AccessProceeding Paper

Comparative Analysis of Structure, Synthesis, and Properties of Polyaniline and Polypyrrole: Insights into Conductive Polymer Variability

by Viktorija Lisyte and Anton Popov

Chem. Proc. 2023, 14(1), 9; https://doi.org/10.3390/ecsoc-27-16058 - 15 Nov 2023

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Abstract

Polypyrrole (PPy) and polyaniline (PANI) nanoparticles were synthesized using a stabilizer—poly(vinyl alcohol) (PVA). The obtained nanostructures of conducting polymers were characterized using advanced analytical techniques such as scanning electron microscopy (SEM), dynamic light scattering (DLS), and ultraviolet–visible spectroscopy (UV-Vis). These comprehensive analyses provided [...] Read more.

Polypyrrole (PPy) and polyaniline (PANI) nanoparticles were synthesized using a stabilizer—poly(vinyl alcohol) (PVA). The obtained nanostructures of conducting polymers were characterized using advanced analytical techniques such as scanning electron microscopy (SEM), dynamic light scattering (DLS), and ultraviolet–visible spectroscopy (UV-Vis). These comprehensive analyses provided valuable insights into the morphology, size distribution, and spectral characteristics of the nanostructures, contributing to a deeper understanding of their potential applications in materials science and nanotechnology. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1751 KiB

Open AccessProceeding Paper

Crystal Structure of 2-(Ethoxymethylene)malononitrile and DFT Evaluation of the C-H···N≡C Close Contacts Energy

by Vyacheslav S. Grinev, Ilya A. Demeshko, Anna E. Sklyar and Alevtina Yu. Yegorova

Chem. Proc. 2023, 14(1), 10; https://doi.org/10.3390/ecsoc-27-16052 - 15 Nov 2023

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Abstract

2-(Ethoxymethylene)malononitrile (1) is a very convenient building block for the construction of various heterocycles and it is assumed to be an intermediate in different three-component reactions. Here, we present the results of XRD of (1) demonstrating the linkage of the co-oriented [...] Read more.

2-(Ethoxymethylene)malononitrile (1) is a very convenient building block for the construction of various heterocycles and it is assumed to be an intermediate in different three-component reactions. Here, we present the results of XRD of (1) demonstrating the linkage of the co-oriented molecules in crystal via C-H···N≡C non-covalent interactions. To evaluate the energy of such interactions, we conducted DFT simulations. The molecules of (1) are linked into infinite chains via C-H···N≡C close contacts with a distance of 2.494 Å. When performing theoretical measurements of the energy of H···N non-covalent interactions by DFT, it was determined by the M06-2X functional, equal to −1.20 kcal/mol, meaning weak attraction. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1782 KiB

Open AccessProceeding Paper

Synthesis of Gold Nanorods for Multifaceted Applications

by Marina Sidorova and Anton Popov

Chem. Proc. 2023, 14(1), 11; https://doi.org/10.3390/ecsoc-27-16057 - 15 Nov 2023

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Abstract

Different length gold nanorods (AuNRs) were synthesized using different methods. The obtained AuNRs were characterized using scanning electron microscopy (SEM), dynamic light scattering (DLS) technique, and UV-Vis spectroscopy. These techniques allowed for a detailed study of the structural and optical properties of the [...] Read more.

Different length gold nanorods (AuNRs) were synthesized using different methods. The obtained AuNRs were characterized using scanning electron microscopy (SEM), dynamic light scattering (DLS) technique, and UV-Vis spectroscopy. These techniques allowed for a detailed study of the structural and optical properties of the AuNRs and provided valuable insights into the synthesis. The characterization results were crucial to guide the synthesis and to further understand the potential applications of AuNRs. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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394 KiB

Open AccessProceeding Paper

Quality Control in Cosmetics: A Five-Year Screening Survey on the Content of Phthalates in Colognes

by Natalia Aldegunde-Louzao, Manuel Lolo-Aira and Carlos Herrero-Latorre

Chem. Proc. 2023, 14(1), 12; https://doi.org/10.3390/ecsoc-27-16118 - 15 Nov 2023

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Abstract

Phthalate esters are used in colognes and other cosmetics and related products to maintain fragrance. Additionally, phthalates can dissolve and stabilize certain aroma ingredients and essential oils. The results of a five-year study (2016–2020) conducted in a quality control laboratory on the presence [...] Read more.

Phthalate esters are used in colognes and other cosmetics and related products to maintain fragrance. Additionally, phthalates can dissolve and stabilize certain aroma ingredients and essential oils. The results of a five-year study (2016–2020) conducted in a quality control laboratory on the presence of phthalate esters in various cosmetic products are presented. A total of 1147 samples from four cologne categories: eau de toilette, eau de cologne, fragrance, and perfume were analyzed using gas chromatography–mass spectrometry (GC-MS/MS) for the quantification of the nine different phthalate esters (BBP, DEHP, DNOP, DNPP, DBP, DIPP, DMEP, DMP, and PIPP) in each category. The results revealed the absence of phthalates at concentrations above the threshold limit (1 µg mL⁻¹) in 95% of the samples analyzed. However, different levels of phthalates were detected in 57 samples, mainly DEHP and DBP. Our findings also demonstrate distinct phthalate profiles according to cologne type, with relevant variations among the four cologne categories analyzed. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1277 KiB

Open AccessProceeding Paper

Density Functional Theory Study on Ring-Chain Isomerism of Semicarbazones

by Alexander S. Kuvakin, Anastasia A. Fesenko and Anatoly D. Shutalev

Chem. Proc. 2023, 14(1), 13; https://doi.org/10.3390/ecsoc-27-16085 - 15 Nov 2023

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Abstract

The conversion of semicarbazones to 1,2,4-triazolidin-3-ones and vice versa (ring-chain isomerism) was studied using the DFT B3LYP/6-311++G(d,p) method. The thermodynamic and kinetic characteristics of this reaction were calculated and discussed. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1057 KiB

Open AccessProceeding Paper

Regioselective Synthesis of Spiro-Oxindoles via a Ruthenium-Catalyzed Metathesis Reaction

by Pradip Debnath

Chem. Proc. 2023, 14(1), 14; https://doi.org/10.3390/ecsoc-27-16131 - 15 Nov 2023

Viewed by 196

Abstract

Spiro-oxindoles are important heterocyclic motifs found in various alkaloids, many of which exhibit pharmacological properties. Due to the remarkable biological activity of spiro-oxindoles, significant effort has been made towards the synthesis of substituted spiro-oxindoles. In this paper, preliminary results regarding the synthesis of [...] Read more.

Spiro-oxindoles are important heterocyclic motifs found in various alkaloids, many of which exhibit pharmacological properties. Due to the remarkable biological activity of spiro-oxindoles, significant effort has been made towards the synthesis of substituted spiro-oxindoles. In this paper, preliminary results regarding the synthesis of 3,3′-spiro pentacyclo-oxindole derivatives via the ring-closing metathesis of 3,3-diallyl oxindoles are reported. The ring-closing metathesis reaction proceeded smoothly with Grubb’s catalyst-I (2 mol%) in toluene at room temperature. The desired products, 3,3′-spiro pentacyclo-oxindoles, were obtained in good to excellent yields under standard reaction conditions. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1316 KiB

Open AccessProceeding Paper

Polyaniline Derivatives for Chemical Sensors of Ammonia Vapor

by R. B. Salikhov, A. A. Gaskarova, T. R. Salikhov, A. D. Ostaltsova and T. T. Yumalin

Chem. Proc. 2023, 14(1), 15; https://doi.org/10.3390/ecsoc-27-16116 - 15 Nov 2023

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Abstract

This study considers the possibility of using thin films of new soluble modified polyaniline derivatives in the creation of chemical sensors. The study involves an examination of how the current passing through resistive structures, which are constructed using thin films of polyanilines, is [...] Read more.

This study considers the possibility of using thin films of new soluble modified polyaniline derivatives in the creation of chemical sensors. The study involves an examination of how the current passing through resistive structures, which are constructed using thin films of polyanilines, is influenced by varying concentrations of ammonia vapors present in the surrounding air. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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549 KiB

Open AccessProceeding Paper

Interaction of Phenolic Schiff Bases Bearing Sulfhydryl Moieties with 2,2-Diphenyl-1-picrylhydrazyl Radical: Structure–Activity Relationship Study

by Iveta Turomsha, Maxim Gvozdev, Natalia Loginova, Galina Ksendzova and Nikolai Osipovich

Chem. Proc. 2023, 14(1), 16; https://doi.org/10.3390/ecsoc-27-16113 - 15 Nov 2023

Viewed by 262

Abstract

Current research on synthetic and naturally occurring phenolic compounds is centered around their prominent antioxidant properties. Since reactive oxygen (ROS) and nitrogen (RNS) species cause considerable damage to cellular components upon their overproduction, associated with the pathogenesis of degenerative, cardiovascular and oncological diseases, [...] Read more.

Current research on synthetic and naturally occurring phenolic compounds is centered around their prominent antioxidant properties. Since reactive oxygen (ROS) and nitrogen (RNS) species cause considerable damage to cellular components upon their overproduction, associated with the pathogenesis of degenerative, cardiovascular and oncological diseases, antioxidants may reduce the risk of developing such conditions. Because hydroxyl, amino and sulfhydryl groups present in their structure, antioxidants may function as hydrogen atom and electron donors, as well as metal-reducing and metal-chelating agents. We synthesized phenolic Schiff bases from 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde; ortho-, meta- and para-mercaptoanilines; and 2,2′- and 4,4′-disulfanediyldianilines. Their antioxidant properties were studied in a 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging assay. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1485 KiB

Open AccessProceeding Paper

An Optimised Method to Synthesise N₅O₂ Aminophenols

by Paula Oreiro-Martínez, Julio Corredoira-Vázquez, Jesús Sanmartín-Matalobos and Matilde Fondo

Chem. Proc. 2023, 14(1), 17; https://doi.org/10.3390/ecsoc-27-16145 - 15 Nov 2023

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Abstract

Aminophenol compounds are usually employed in coordination chemistry due to their versatility to form metal complexes. Heptadentate N₅O₂ aminophenol ligands can lead to the formation of lanthanoid complexes with pentagonal bypiramidal (pbp) geometry, which are very interesting in the field [...] Read more.

Aminophenol compounds are usually employed in coordination chemistry due to their versatility to form metal complexes. Heptadentate N₅O₂ aminophenol ligands can lead to the formation of lanthanoid complexes with pentagonal bypiramidal (pbp) geometry, which are very interesting in the field of molecular magnetism. In this communication, we report an optimised method for obtaining two similar N₅O₂ aminophenols named 2-((((6-(((5-hydroxy-2-R-benzyl)(pyridin-2-ylmethyl)amino)methyl)pyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)methyl)-4-R-phenol (R = methyl or methoxy), which significantly improves the few examples of synthesis of this type of compound reported in the literature. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1231 KiB

Open AccessProceeding Paper

One-Pot Synthesis of Phosphoramidates from dibenzo[1,3,2]dioxaphosphepine-6-oxide

by Giacomo Marra, Marco Bortoluzzi and Lodovico Agostinis

Chem. Proc. 2023, 14(1), 18; https://doi.org/10.3390/ecsoc-27-16174 - 15 Nov 2023

Viewed by 273

Abstract

Flame retardants play a crucial role in mitigating the hazards associated with fires by impeding their ignition and spread. However, conventional halogen-based flame retardants have encountered environmental and health concerns due to their persistence, bioaccumulation, and potential toxicity. In light of these concerns, [...] Read more.

Flame retardants play a crucial role in mitigating the hazards associated with fires by impeding their ignition and spread. However, conventional halogen-based flame retardants have encountered environmental and health concerns due to their persistence, bioaccumulation, and potential toxicity. In light of these concerns, the present study aimed to develop innovative compounds with potential applications as a flame retardant system that mitigates the drawbacks associated with halogen-based compounds. Several phosphoramidates were synthesized in a single step under mild conditions from the H-phosphonate dibenzo[1,3,2]dioxaphosphepine-6-oxide (BPPO), following a method based on the oxidation of the reactant in the presence of a suitable aliphatic or aromatic amine. The compounds were isolated with high purity, and the formulations were confirmed by multinuclear NMR spectroscopy. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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2489 KiB

Open AccessProceeding Paper

Alternative Synthesis of Phosphonate Derivatives of 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide

by Marco Bortoluzzi, Stefan Ghincolov and Lodovico Agostinis

Chem. Proc. 2023, 14(1), 19; https://doi.org/10.3390/ecsoc-27-16176 - 15 Nov 2023

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Abstract

The phosphonates 6-methoxy-6H-dibenzo[1,2]oxaphosphinine-6-oxide and 6-(allyloxy)-6H-dibenzo[1,2]oxaphosphinine 6-oxide were synthesised in a single step under mild conditions from the H-phosphinate 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), following a method based on the oxidation of the reactant with I₂ in the presence of the reactant alcohol as solvent [...] Read more.

The phosphonates 6-methoxy-6H-dibenzo[1,2]oxaphosphinine-6-oxide and 6-(allyloxy)-6H-dibenzo[1,2]oxaphosphinine 6-oxide were synthesised in a single step under mild conditions from the H-phosphinate 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), following a method based on the oxidation of the reactant with I₂ in the presence of the reactant alcohol as solvent and triethylamine as base. The compounds, of potential interest in the field of non-halogenated flame retardants, were isolated with high purity and the formulations were confirmed via multinuclear NMR spectroscopy. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1104 KiB

Open AccessProceeding Paper

Stability and Reactivity of Tocopherols: Theoretical Study

by Nasséra Benbrahim, Kawther Zeddour-Brahim, Zahia Zizi and Zohra Bengharez

Chem. Proc. 2023, 14(1), 20; https://doi.org/10.3390/ecsoc-27-16043 - 15 Nov 2023

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Abstract

In the search for the tocopherols structure-reactivity relationship, our calculations showed that the GAP, which is the difference between the energy values of the frontier orbitals, decreases during the passage gas/aqueous medium for the isoforms α, β and γ. But it increases for [...] Read more.

In the search for the tocopherols structure-reactivity relationship, our calculations showed that the GAP, which is the difference between the energy values of the frontier orbitals, decreases during the passage gas/aqueous medium for the isoforms α, β and γ. But it increases for isoform δ. This means that the latter is less reactive and less soft than the others in aqueous medium. On the other hand, the chemical descriptors calculations revealed that the transfer of electrons takes place in the direction α < β < γ < δ in the gas state and aqueous medium. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1771 KiB

Open AccessProceeding Paper

One-Pot Synthesis of New 4,5,6,7-tetrahydro-3H-[1,2]dithiolo[3,4-b]pyridines Starting from N,N’-Diphenyldithiomalondiamide

by Ekaterina A. Varzieva, Anna E. Sinotsko, Victor V. Dotsenko and Nicolai A. Aksenov

Chem. Proc. 2023, 14(1), 21; https://doi.org/10.3390/ecsoc-27-16134 - 15 Nov 2023

Viewed by 237

Abstract

Active methylene compounds such as thioamides are widely used in the organic chemistry for the construction of a variety of heterocyclic systems, such as thieno[2,3-b]pyridines, 1,2,4-dithiazoles, isothiazoles, 1,2,3-thiadiazoles, etc. N,N′-Diphenyldithiomalondiamide (dithiomalondianilide) as a compound with methylene active group is also [...] Read more.

Active methylene compounds such as thioamides are widely used in the organic chemistry for the construction of a variety of heterocyclic systems, such as thieno[2,3-b]pyridines, 1,2,4-dithiazoles, isothiazoles, 1,2,3-thiadiazoles, etc. N,N′-Diphenyldithiomalondiamide (dithiomalondianilide) as a compound with methylene active group is also of interest as a starting reagent for the synthesis of new N,S-containing heterocycles with potential pharmacological application. However, the reactions of dithiomalondianilide are poorly studied. In the present study, we report the synthesis of new 4,5,6,7-tetrahydro[1,2]dithiolo[3,4-b]dithiolopyridine-5-carboxamides through the reaction of dithiomalondianilide with 3-aryl-2-cyanoacrylamides. The products were characterized using FTIR and NMR spectroscopy as well as X-ray analysis. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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696 KiB

Open AccessProceeding Paper

4H-[1,3,5,2]Oxadiazaphospholo[3,4-a][1,5]benzodiazepin-1-amine-1-oxides: Synthesis and Computational Studies

by Žilvinas Anusevičius, Lidija Kosychova, Visvaldas Kairys, Kastis Krikštopaitis and Jonas Šarlauskas

Chem. Proc. 2023, 14(1), 22; https://doi.org/10.3390/ecsoc-27-16162 - 15 Nov 2023

Viewed by 287

Abstract

The modification of heterocyclic systems remains one of the most promising areas in heterocyclic chemistry. Benzodiazepines (BZDs), representing a diverse class of heterocyclic molecules, have piqued interest due to their use as anticonvulsant/anti-inflammatory/analgesic/sedative/anti-depressive/hypnotic medications, as well as anti-inflammatory/anti-HIV drugs. Phosphorus heterocycle molecules fused [...] Read more.

The modification of heterocyclic systems remains one of the most promising areas in heterocyclic chemistry. Benzodiazepines (BZDs), representing a diverse class of heterocyclic molecules, have piqued interest due to their use as anticonvulsant/anti-inflammatory/analgesic/sedative/anti-depressive/hypnotic medications, as well as anti-inflammatory/anti-HIV drugs. Phosphorus heterocycle molecules fused with rings of different sizes and bearing various heteroatoms have also been attracting much interest. Phosphoramidate class compounds with an amino group linked directly to the phosphorus atom have gained considerable attention due to their wide range of biological activity and agricultural application. To date, however, only non-condensed monocyclic 1,3,5,2-oxodiazaphosphol-2-oxides have been described.Herein, we report the synthesis of previously undescribed 4H-[1,3,5,2]oxadiazophospho[3,4-a][1,5]benzodiazepine-1-amino-1-oxides, comprising benzodiazepine and a fused five-member oxodiazophospholo cycle with four heteroatoms in the “a” position, which was made possible by phosphorylation of 1,3,4,5-tetrahydro-2H-1,5-benzodiazepin oximes with an equimolar amount of dimethylaminophosphoric acid dichloride. The chemical structures of the compounds were confirmed by IR, ¹H, ¹³C, and ³¹P NMR spectral analysis. A series of simulations were conducted by employing the semi-empirical, tight-binding computational technique GFN2-xTB to reveal the likely pathways leading to their formation. The synthesised compounds obeyed Lipinski’s rule, implying a good bioavailability, and assessment of their projected drug-like abilities revealed that they may have a strong anti-neoplastic activity and, to a lesser extent, may act as both substrates and inducers of cytochrome P-450 (CYP) super-family enzymes. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Synthesis of a Dysprosium(III) Complex with a Hexadentate Amine Ligand

by Cristina González-Barreira, Julio Corredoira-Vázquez, Ana M. García-Deibe and Matilde Fondo

Chem. Proc. 2023, 14(1), 23; https://doi.org/10.3390/ecsoc-27-16143 - 15 Nov 2023

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Abstract

The use of polydentate macrocyclic Lewis bases is a way to contribute to determine the coordination number of metal complexes. In this sense, hexadentate N₆ donors can help to achieve lanthanoid complexes with coordination number 8. But the geometry of these complexes [...] Read more.

The use of polydentate macrocyclic Lewis bases is a way to contribute to determine the coordination number of metal complexes. In this sense, hexadentate N₆ donors can help to achieve lanthanoid complexes with coordination number 8. But the geometry of these complexes depends on the flexibility of the bases. Accordingly, in this communication we present the synthesis and crystallographic characterization of the dysprosium complex [DyL^N6Cl₂]Cl·2H₂O, where L^N6 is a flexible hexaaza donor. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Synthesis of a Hybrid Molecule Based on Biologically Active 5Z,9Z-Eicosadienoic Acid and Vanillin

by Elina Kh. Makarova, Alexey A. Makarov, Lilya U. Dzhemileva and Usein M. Dzhemilev

Chem. Proc. 2023, 14(1), 24; https://doi.org/10.3390/ecsoc-27-16170 - 15 Nov 2023

Viewed by 223

Abstract

A hybrid compound based on (5Z,9Z)-eicosa-5,9-dienoic acid and vanillin was synthesized in high yield (94%) using a new intermolecular cross-cyclomagnesiation reaction of aliphatic and O-containing 1,2-dienes catalyzed by Cp₂TiCl₂. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1858 KiB

Open AccessProceeding Paper

Efficient Solvent Extraction of Phenol Using Imidazolium-Based Ionic Liquids

by Imane Hamzi, Souad Bouchakour, Bachir Mostefa-Kara and Didier Villemin

Chem. Proc. 2023, 14(1), 25; https://doi.org/10.3390/ecsoc-27-16151 - 15 Nov 2023

Viewed by 269

Abstract

Ionic Liquids (ILs) have gained significant attention in both industry and academia due to their unique properties and diverse applications. With countless possible combinations of cations (e.g., Ammonium, Sulfonium, Phosphonium) and anions (Organic or Inorganic), the variety of ILs is immense. Among them, [...] Read more.

Ionic Liquids (ILs) have gained significant attention in both industry and academia due to their unique properties and diverse applications. With countless possible combinations of cations (e.g., Ammonium, Sulfonium, Phosphonium) and anions (Organic or Inorganic), the variety of ILs is immense. Among them, Imidazolium salts form the largest IL family, making them a focal point in this study. Phenolic compounds, essential in the chemical industry, become hazardous to both human and aquatic life when released into the environment. Traditional separation methods for phenolics unfortunately involve environmentally problematic processes. This research focuses on synthesizing and characterizing Imidazolium-functionalized ILs ([EtO₂C₂mim]Br, [EtO₂C₂mim]BF₄, [EtO₂C₂mim]PF₆) and studying their phenol extraction abilities. The results revealed [EtO₂C₂mim]Br as the most effective, extracting 99% of phenol and offering a promising alternative for the efficient extraction of phenols from real coal liquefaction oil. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Synthesis and Optimization of Fluid Properties of 3D-Printed Modified Chitosan Biopolymer Composite Membranes

by Anthony C. Ogazi and Peter O. Osifo

Chem. Proc. 2023, 14(1), 26; https://doi.org/10.3390/ecsoc-27-16136 - 15 Nov 2023

Viewed by 275

Abstract

The study investigates the synthesis and optimization of modified chitosan-silver nanoparticles-graphene oxide (CS/AgNP/GO) composite ink’s chemical and physical properties using inkjet 3D printing technology with the incorporation of polyvinyl alcohol (PVA) as a plasticizer. The variation in the concentration of PVA co-solvent affected [...] Read more.

The study investigates the synthesis and optimization of modified chitosan-silver nanoparticles-graphene oxide (CS/AgNP/GO) composite ink’s chemical and physical properties using inkjet 3D printing technology with the incorporation of polyvinyl alcohol (PVA) as a plasticizer. The variation in the concentration of PVA co-solvent affected drop ejection from the nozzle orifice. An increase in the PVA mole fraction minimized the entanglement within the CS molecular structure, improved flow rate, and subsequently formed spherical ink droplets on the substrate at 1140.0 Kg/m³ (density), 0.00748 Pas (viscosity), and 55.6 mN/m (surface tension), indicating that the solvent was responsible for lowering the rheological properties of the composite membranes. The optimized drop velocity was achieved at 1.8 m/s, which also yielded adequate drop formation void of ligament. Therefore, it is very essential to adhere to the printer’s ink specifications in order to formulate appropriate generic modified CS ink with an acceptable minimum fluid drop velocity to ensure quality inkjet-printed biopolymer composite membranes for different industrial applications. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Photochemical and Photobiological Activity of Zn, Cu, Ni, Co, Fe and Mn Unsubstituted Phthalocyanines

by Franklin Vargas, Miguel León, Álvaro Álvarez, Sergio Dasilva and Alexis Maldonado

Chem. Proc. 2023, 14(1), 27; https://doi.org/10.3390/ecsoc-27-16171 - 15 Nov 2023

Viewed by 289

Abstract

Phthalocyanines are a group of porphyrin synthetic molecules. These compounds show outstanding photodynamic properties. This is due to their high ability to photogenerate free radicals, such as ¹O₂ and O^.−₂. However, the presence of different metals in the [...] Read more.

Phthalocyanines are a group of porphyrin synthetic molecules. These compounds show outstanding photodynamic properties. This is due to their high ability to photogenerate free radicals, such as ¹O₂ and O^.−₂. However, the presence of different metals in the central core of phthalocyanines are able to modulate these characteristics. This study demonstrated that the photochemical activity of Zn, Cu, Ni, Co, Fe and Mn unsubstituted phthalocyanines differs, depending on the size and electronic configuration of the central metal. In addition, phthalocyanines showed different levels of photodamage against plasmid pBR322. Outcoming computational calculations will aim to clarify the photodynamic mechanisms of phthalocyanines. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Microwave Activation: Solventless Catalysed Synthesis of Cross Conjugated Dienones of Tropinone

by Renata Gasparova, Didier Villemin and Nathalie Bar

Chem. Proc. 2023, 14(1), 28; https://doi.org/10.3390/ecsoc-27-16155 - 15 Nov 2023

Viewed by 343

Abstract

Cross-conjugated dienones are very important biologically active products. The condensation of N-methyl-8-azabicyclo[3.2.1]-bicyclo[3.2.1]octan-3-one (tropinone) with aromatic aldehydes takes place in the presence of acidic (K10 clay, silica) or basic catalysts (alumina, KF-alumina). The best yields of (2E,4E)-2,4-bis-arylmethylene-8-methyl-8-azabicyclo[3.2.1]octan-3-ones were obtained with the K10 [...] Read more.

Cross-conjugated dienones are very important biologically active products. The condensation of N-methyl-8-azabicyclo[3.2.1]-bicyclo[3.2.1]octan-3-one (tropinone) with aromatic aldehydes takes place in the presence of acidic (K10 clay, silica) or basic catalysts (alumina, KF-alumina). The best yields of (2E,4E)-2,4-bis-arylmethylene-8-methyl-8-azabicyclo[3.2.1]octan-3-ones were obtained with the K10 clay under microwave irradiation without solvent. New dienones derived from tropinone will be tested in various biological assays. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

In Silico Pharmacological Prediction of Substituted Aminonitriles

by Bianca Araújo Fernandes Veras, Pamela Isabel Japura Huanca, Igor de Sousa Oliveira, Rafael Trindade Maia, Helivaldo Diogenes da Silva Souza and Sávio Benvindo Ferreira

Chem. Proc. 2023, 14(1), 29; https://doi.org/10.3390/ecsoc-27-16178 - 15 Nov 2023

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Abstract

Aminonitriles are heterocyclic compounds commonly used as intermediates in the synthesis of various compounds, but which have versatility in physiological processes, with peculiar characteristics and high biological value that still need to be investigated with greater avidity. Given this perspective, the present study [...] Read more.

Aminonitriles are heterocyclic compounds commonly used as intermediates in the synthesis of various compounds, but which have versatility in physiological processes, with peculiar characteristics and high biological value that still need to be investigated with greater avidity. Given this perspective, the present study aimed to determine the probability of substituted aminonitriles interacting with classes of pharmacological targets in the human body. For this, eight aminonitriles (HAN-1 to HAN-8) were synthesized and used in the in silico prediction of the compounds, using the Molinspiration software, where the potentiality of the substances to act as a G protein coupled receptor (GPCR) ligand, an ion channel modulator, a kinase inhibitor, a nuclear receptor ligand, a protease inhibitor and an enzyme inhibitor was evaluated. Thus, it was observed that the molecules showed moderate bioactivity in 100% of cases as a GPCR ligand (−0.27 to −0.5), 87.5% as an enzyme inhibitor (−0.33 to −0.49), 75% as a kinase inhibitor (−0.39 to −0.5), 62.5% as an ion channel modulator (−0.3 to −0.47) and as a protease inhibitor (−0.45 to −0.49), and 37.5% as nuclear receptor ligand (−0.43 to −0.46). The computational analysis carried out in this study indicated that the HAN-4 and HAN-6 molecules were the only molecules that reached a considerable activity score for all classes of proposed pharmacological targets, thus being the most promising as possible therapeutic tools, with further advances in studies on the performance of pre-clinical and clinical tests to verify their real bioactivity still being necessary. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Transesterification of a Natural Epoxythymol Is Favored under Alkaline Conditions, Preserving the Enantiomeric Purity

by Jessica M. Lorenzo-García, Antonio J. Oliveros-Ortiz, Héctor M. Arreaga-González, Carlos J. Cortés-García, Rosa E. del Río, Gabriela Rodríguez-García and Mario A. Gómez-Hurtado

Chem. Proc. 2023, 14(1), 30; https://doi.org/10.3390/ecsoc-27-16140 - 15 Nov 2023

Viewed by 240

Abstract

Transesterification is a synthetic chemistry strategy promoted in acid or alkaline conditions, yielding a structural diversity of organic compounds. Epoxythymols comprise a class of chiral natural compounds with biological relevance, and the literature describes their chiral purity loss during acid transesterification reactions. This [...] Read more.

Transesterification is a synthetic chemistry strategy promoted in acid or alkaline conditions, yielding a structural diversity of organic compounds. Epoxythymols comprise a class of chiral natural compounds with biological relevance, and the literature describes their chiral purity loss during acid transesterification reactions. This work reports the basic transesterification of the natural derivative (8S)-10-benzoylxy-8,9-epoxy-6-hydroxythymol under alkaline conditions. Herein, the formation of (8S)-10-benzoylxy-6-isobutyryloxy-8,9-epoxythymol isobutyrate is gained, avoiding the loss of optical purity. ¹H NMR-BINOL experiments revealed the enantiomeric purity of the product reaction. These results highlight that the implemented strategy promotes transesterification, preserving optical purity. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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909 KiB

Open AccessProceeding Paper

A New Synthesis of Polyheterocyclic Compounds Containing Nitrogen and Boron Atoms

by Victor Yu Kirsanov and Elena B. Rakhimova

Chem. Proc. 2023, 14(1), 31; https://doi.org/10.3390/ecsoc-27-16103 - 15 Nov 2023

Viewed by 226

Abstract

Tetraazatricyclanes containing two boron atoms in the molecular framework were synthesized for the first time via the heterocyclization reaction of tetraamines with tetrakis(dimethylamino)diborane. Tetrakis(dimethylamino)diborane is a new starting reagent in the synthesis of polyheterocyclic compounds that may be of interest as cytotoxic agents. [...] Read more.

Tetraazatricyclanes containing two boron atoms in the molecular framework were synthesized for the first time via the heterocyclization reaction of tetraamines with tetrakis(dimethylamino)diborane. Tetrakis(dimethylamino)diborane is a new starting reagent in the synthesis of polyheterocyclic compounds that may be of interest as cytotoxic agents. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1017 KiB

Open AccessProceeding Paper

Clay Catalysis: Solventless Condensation of Benzofuran-3(2H)-One with α,β-Dicarbonyl Compounds under Microwave Irradiation: Synthesis of New Acyl-Aurones

by Karima Boussafi, Didier Villemin and Nathalie Bar

Chem. Proc. 2023, 14(1), 32; https://doi.org/10.3390/ecsoc-27-16154 - 15 Nov 2023

Viewed by 279

Abstract

Aurones are natural bioactive dyes found in plants, and many of them are biologically active. We reported herein that α,β-dicarbonyl compounds condense with 3-coumarones without a solvent under microwave irradiation with clay as a catalyst. Novel acylaurones were obtained in good yields; the [...] Read more.

Aurones are natural bioactive dyes found in plants, and many of them are biologically active. We reported herein that α,β-dicarbonyl compounds condense with 3-coumarones without a solvent under microwave irradiation with clay as a catalyst. Novel acylaurones were obtained in good yields; the more stable E-isomer was formed stereoselectively. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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920 KiB

Open AccessProceeding Paper

Spectroscopic Investigation, Component Analysis, and DFT Calculations of Tautomeric Forms of Substituted Dihydro-6H-chromeno[4,3-d]pyrazolo[1,5-a]pyrimidin-6-one

by Olga A. Mazhukina, Ekaterina M. Arzyamova, Vyacheslav S. Grinev and Alevtina Yu. Yegorova

Chem. Proc. 2023, 14(1), 33; https://doi.org/10.3390/ecsoc-27-16106 - 15 Nov 2023

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Abstract

Chromenopirazolopyrimidinone (CPP) was synthesized using microwave radiation in the absence of solvent by a multicomponent reaction of 4-hydroxy-2H-chromen-2-one with 5-amine-1H-pyrazole and benzaldehyde. CPP exists as a mixture of tautomeric forms, the structure of which was examined by means of spectroscopic methods and quantum [...] Read more.

Chromenopirazolopyrimidinone (CPP) was synthesized using microwave radiation in the absence of solvent by a multicomponent reaction of 4-hydroxy-2H-chromen-2-one with 5-amine-1H-pyrazole and benzaldehyde. CPP exists as a mixture of tautomeric forms, the structure of which was examined by means of spectroscopic methods and quantum chemistry. As was shown by the MILCA algorithm, UV-Vis spectra obtained in different solvents of various polarities contain bands of all tautomeric forms. Decomposition of the absorption spectra of CPP in various solvents on the individual components of the absorption showed the presence of two tautomers. The molar ratios of tautomeric forms depend on the polarity of the solvent used. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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360 KiB

Open AccessProceeding Paper

Prospects of Using Epidermal Secretion of Scaleless Fish Species as a Source of Peptide Complexes with Antioxidant Activity

by Lyudmila Perkova and Elena Grekhneva

Chem. Proc. 2023, 14(1), 34; https://doi.org/10.3390/ecsoc-27-16161 - 15 Nov 2023

Viewed by 243

Abstract

Every year, peptide-based preparations are becoming more and more in demand in medicine. Therefore, the identification and study of new biomaterials that are sources of regulatory peptides are an urgent tasks. This study considers the epidermal secretion of the African catfish (Clarias gariepinus) [...] Read more.

Every year, peptide-based preparations are becoming more and more in demand in medicine. Therefore, the identification and study of new biomaterials that are sources of regulatory peptides are an urgent tasks. This study considers the epidermal secretion of the African catfish (Clarias gariepinus) as a readily available raw material for the preparation of peptide complexes. In the history of peptide drug synthesis, this substance was first investigated as a source for obtaining regulatory peptides with antioxidant activity. We applied a new approach to the process of the isolation of biologically active peptide fractions, thereby reducing the time and increasing the yield of the target product. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Larvicidal Potency of Some Selected Nigerian Plants against Aedes aegypti

by Eze E. Ajaegbu, Gloria T. Onah, Adeniran J. Ikuesan and Abdulrasheed M. Bello

Chem. Proc. 2023, 14(1), 35; https://doi.org/10.3390/ecsoc-27-16156 - 15 Nov 2023

Viewed by 406

Abstract

Many public health-related problems, such as dengue diseases, are caused by the vector Aedes aegypti. This paper’s objective is to develop larvicidal activities against the larvae of Ae. aegypti. Standard methods were utilized for the collection, extraction, and phytochemical screening of [...] Read more.

Many public health-related problems, such as dengue diseases, are caused by the vector Aedes aegypti. This paper’s objective is to develop larvicidal activities against the larvae of Ae. aegypti. Standard methods were utilized for the collection, extraction, and phytochemical screening of the plant parts and extracts. Different extract concentrations were tested against the larvae of Ae. aegypti mosquitoes. The different toxicities observed were due to changes in the compounds present in each of the plant extracts. Seven phytochemical constituents were detected for plant extracts. Nigerian medicinal plants could be used to curb the spread of the dengue vector, Aedes aegypti. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

DFT and Multinuclear NMR Spectroscopy in the Study of Five-Membered Saturated Metallocarbocycles of Main III Group Metals

by Tatyana V. Tyumkina and Denis N. Islamov

Chem. Proc. 2023, 14(1), 36; https://doi.org/10.3390/ecsoc-27-16048 - 15 Nov 2023

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Abstract

Five-membered saturated metallacarbocycles represent a large family of organometallic compounds, which are frequently postulated as reactive intermediates in catalysis or as precursors for the synthesis of a wide range of functionally substituted compounds, however, their NMR spectral data are incomplete and not systematized. [...] Read more.

Five-membered saturated metallacarbocycles represent a large family of organometallic compounds, which are frequently postulated as reactive intermediates in catalysis or as precursors for the synthesis of a wide range of functionally substituted compounds, however, their NMR spectral data are incomplete and not systematized. Metallacarbocycles for Main III Group metals, which are spectroscopically characterized, are described in this article. Among these, of particular interest are 1-ethyl-3-substituted alumolanes, 3-spiro-substituted polycyclic alumolanes and nonbornen annelated alumolanes, which are supposedly formed by alkene cycloalumination with AlEt₃ catalyzed by Cp₂ZrCl₂. Conformational analysis upon inversion of a five-membered ring for mono and polycyclic alumolanes is presented. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Synthesis and Diversification of Chiral Spirooxindoles via Organocatalytic Cascade Reactions

by Jessica Navarro Vega, David Cruz Cruz and Clarisa Villegas Gómez

Chem. Proc. 2023, 14(1), 37; https://doi.org/10.3390/ecsoc-27-16100 - 15 Nov 2023

Viewed by 279

Abstract

The synthesis of chiral spirooxindoles through different amino catalytic activation modes is described herein. Several alkenylisatins were obtained from the Knoevenagel reaction of isatin and activated methylene derivatives containing electron withdrawing groups such as ethyl cyanoacetate. A spirooxindole derivative was obtained from the [...] Read more.

The synthesis of chiral spirooxindoles through different amino catalytic activation modes is described herein. Several alkenylisatins were obtained from the Knoevenagel reaction of isatin and activated methylene derivatives containing electron withdrawing groups such as ethyl cyanoacetate. A spirooxindole derivative was obtained from the oxa-Michael-Michael reaction between one of the synthesized alkenylisatins and 2-hydroxycinnamaldehyde. Currently, new methodologies that allow access to spirooxindole scaffolds are being explored, mainly though Diels-Alder reactions between 2-methylenindolin-2-ones and aldehydes via the trienamine activation mode. The following cascade reactions will be explored in the future to obtain the proposed polycyclic spirooxindole derivatives. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Study of the Influence of a Solvent on the Crystal Structure of an Ethyl-Substituted Bisthiosemicarbazone Ligand

by Sandra Fernández-Fariña, Uxía Barreiro-Sisto, Isabel Velo-Heleno and Ana M. González-Noya

Chem. Proc. 2023, 14(1), 38; https://doi.org/10.3390/ecsoc-27-16105 - 15 Nov 2023

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Abstract

A potentially dianionic symmetric bisthiosemicarbazone ligand H₂L^Et has been prepared by a condensation reaction between two equivalents of 4-N-ethyl-3-thiosemicarbazide and one equivalent of 4,4′-methylenebis(acetophenone). The crystal structures obtained from solvents with different donor abilities were studied. The recrystallization of [...] Read more.

A potentially dianionic symmetric bisthiosemicarbazone ligand H₂L^Et has been prepared by a condensation reaction between two equivalents of 4-N-ethyl-3-thiosemicarbazide and one equivalent of 4,4′-methylenebis(acetophenone). The crystal structures obtained from solvents with different donor abilities were studied. The recrystallization of H₂L^Et from methanol and dimethylsulfoxide enables the isolation of single crystals suitable for the X-ray diffraction studies of [H₂L^Et] 1 and [H₂L^Et]·CH₃SOCH₃2, respectively. This study shows that the solvent does not affect the macrostructure but influences the microstructure of the ethyl-substituted bisthiosemicarbazone ligand H₂L^Et. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Design, Synthesis and Characterization of a Bicompartmental bisthiosemicarbazone Ligand

by Isabel Velo-Heleno, Sandra Fernández-Fariña, Uxía Barreiro-Sisto, Laura Rodríguez-Silva and Rosa Pedrido

Chem. Proc. 2023, 14(1), 39; https://doi.org/10.3390/ecsoc-27-16093 - 15 Nov 2023

Viewed by 274

Abstract

In this work, we present the design and synthesis of the bisthiosemicarbazone ligand H₃L^Me by means of an iminic condensation reaction between 2-hydroxyisophthalaldehyde and 4-methyl-3-thiosemicarbazide. This ligand is bicompartmental, pentadentate [N₂S₂O] and potentially trianionic. The [...] Read more.

In this work, we present the design and synthesis of the bisthiosemicarbazone ligand H₃L^Me by means of an iminic condensation reaction between 2-hydroxyisophthalaldehyde and 4-methyl-3-thiosemicarbazide. This ligand is bicompartmental, pentadentate [N₂S₂O] and potentially trianionic. The presence of a spacer constituted by a phenol group facilitates the coordination of transition metal ions, giving rise to a great variety of structures. To confirm the purity of the ligand, different characterization techniques were employed, including elemental analysis, mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance. The acquisition of suitable crystals of H₃L^Me allowed us to analyze its structure through X-ray diffraction studies. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Molecular Dynamics Simulations on the Mesophilic Enzyme Vibrio Cholerae Endonuclease I: Salt Effect Study

by Djamila Benrezkallah

Chem. Proc. 2023, 14(1), 40; https://doi.org/10.3390/ecsoc-27-16165 - 15 Nov 2023

Viewed by 282

Abstract

Some of the most extensively studied marine or estuarine bacteria belong to the genus Vibrio, with Vibrio cholerae being the most notorious species as it is the cause of cholera in humans. V. cholerae is found in tropical and temperate areas and [...] Read more.

Some of the most extensively studied marine or estuarine bacteria belong to the genus Vibrio, with Vibrio cholerae being the most notorious species as it is the cause of cholera in humans. V. cholerae is found in tropical and temperate areas and can be classified as a mesophilic bacterium with its growth optimum at around 37 °C. One of the important factors in the activity and stability of each enzyme is its physiological environment. A previous study on the secreted mesophilic enzyme Endonuclease I from the Vibrio cholerae genus (VcEndA) showed that its activity was strongly dependent not only on temperature but also on NaCl concentration. Here, we report a structural study on the mesophilic enzyme (VcEndA) using molecular dynamics simulations at different salt concentrations (NaCl). The analysis of molecular dynamic simulation trajectories reveals that the enzyme is not tolerant and not sensitive to salt since the profile of the rmsf as a function of different concentrations does not show a large difference in the mobility of the enzyme for high values of the NaCl concentration (450 and 650 mM). However, the most flexible regions of the enzyme are recorded under the concentration of 175 mM, which coincides well with the previous experimental work. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Breast Cancer Screening Using Artificial Intelligence Techniques: Enhancing Biochemical Insights and Diagnostic Accuracy

by Richa Gupta and Mohsina Bilal

Chem. Proc. 2023, 14(1), 41; https://doi.org/10.3390/ecsoc-27-16121 - 15 Nov 2023

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Abstract

Breast cancer, the most prevalent cancer in women worldwide, demands effective screening for early identification and improved treatment outcomes. Recent advances in artificial intelligence (AI) have resulted in dramatic developments in a variety of fields, including healthcare. In this review paper, we look [...] Read more.

Breast cancer, the most prevalent cancer in women worldwide, demands effective screening for early identification and improved treatment outcomes. Recent advances in artificial intelligence (AI) have resulted in dramatic developments in a variety of fields, including healthcare. In this review paper, we look at how AI approaches can be used in breast cancer screening to improve diagnostic accuracy and provide deeper molecular insights. We dig into the complex terrain of breast cancer treatment, which has transformed as a result of the discovery of prognostic and predictive biomarkers, allowing for personalised therapeutic methods based on molecular subgroups. We emphasise the importance of AI-driven approaches in optimising screening procedures and providing quick and exact findings. The potential of AI to revolutionise breast cancer screening is highlighted, including its applications in diagnostic imaging, lesion identification, and standardised imaging data interpretation. The analysis highlights AI’s critical role in tackling issues associated with the integration of new technologies, providing solutions for worldwide standardisation in cancer detection. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

The Synthesis of Various 2-Imino-2H-chromene-3-carbonitrile Derivatives

by Anna A. Meshcheryakova, Ekaterina A. Konstantinova, Karina A. Melkonyan, Alexandra A. Khrustaleva and Vitaliy V. Sorokin

Chem. Proc. 2023, 14(1), 42; https://doi.org/10.3390/ecsoc-27-16125 - 15 Nov 2023

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Abstract

One-pot and stepwise reactions of salicylic aldehydes (salicylic, 5-bromsalicylic) and different equivalents of malononitrile and their mutual transformations were investigated. Various derivatives of 2-imino-2H-chromene-3-carbonitrile were isolated. This work reports the synthesis of novel 2-(4-amino-9-R-1-cyano-5-imino-3,5-dihydro-2H-chromeno[3,4-c]pyridin-2-ylidene)malononitriles. The influence of reaction parameters, such as ultrasound activation [...] Read more.

One-pot and stepwise reactions of salicylic aldehydes (salicylic, 5-bromsalicylic) and different equivalents of malononitrile and their mutual transformations were investigated. Various derivatives of 2-imino-2H-chromene-3-carbonitrile were isolated. This work reports the synthesis of novel 2-(4-amino-9-R-1-cyano-5-imino-3,5-dihydro-2H-chromeno[3,4-c]pyridin-2-ylidene)malononitriles. The influence of reaction parameters, such as ultrasound activation conditions, solvent type, and the presence or absence of a catalyst, was studied in this work. The structures of the synthesized compounds were established using spectroscopic data (IR, NMR). Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Synthesis and Cytotoxic Activity of Conjugates of Mitochondrial-Directed Cationic Compound F16 with Ursane-Structure Triterpenic Acids Containing a Polyhydroxylated A-ring

by Anna Spivak, Darya Nedopekina and Eldar Davletshin

Chem. Proc. 2023, 14(1), 43; https://doi.org/10.3390/ecsoc-27-16177 - 15 Nov 2023

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Abstract

We chemically linked corosolic and asiatic acids and a synthetic polyoxygenated analogue of ursolic acid via an alkyl linker to the cationic mitochondrial targeting compound F16 (4-(1H-indole-3-ylvinyl)-N-methylpyridinium iodide). The conjugates were tested for cytotoxic activity against two human lung adenocarcinoma cell [...] Read more.

We chemically linked corosolic and asiatic acids and a synthetic polyoxygenated analogue of ursolic acid via an alkyl linker to the cationic mitochondrial targeting compound F16 (4-(1H-indole-3-ylvinyl)-N-methylpyridinium iodide). The conjugates were tested for cytotoxic activity against two human lung adenocarcinoma cell lines, H1299 and A549, and non-cancerous mouse embryonic fibroblast cells. The results showed that conjugation of polyoxygenated triterpene acids with the terminal cationic fragment F16 in the C-28 side chain enhanced cytotoxicity (30–35 fold) compared to the original natural ursolic acid. However, the presence of hydroxyl or acetyl functions in the A-ring of F16 conjugates of corosolic or asiatic acids resulted in a significant decrease in cytotoxicity compared to their structural analogue, the F16 derivative of ursolic acid. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Uranyl Acetate, a Lewis Acid Catalyst for Acetoxylation of Monoterpenic and Steroidal Alcohols

by Juan Enrique Tacoronte Morales, Carla Bernal Villavicencio, Xavier Leopoldo Gracia Cervantes, Maria Elizabeth Canchingre and Maria Teresa Cabrera Pedroso

Chem. Proc. 2023, 14(1), 44; https://doi.org/10.3390/ecsoc-27-16064 - 15 Nov 2023

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Abstract

The use of heterogeneous catalytic systems in the production of esters of secondary alcohols (monoterpenic and steroidal) allows us to obtain satisfactory yields of these derivatives widely used in the industry. The use of the heterogeneous system uranyl acetate/chloroform-acetonitrile, under laboratory conditions, allows [...] Read more.

The use of heterogeneous catalytic systems in the production of esters of secondary alcohols (monoterpenic and steroidal) allows us to obtain satisfactory yields of these derivatives widely used in the industry. The use of the heterogeneous system uranyl acetate/chloroform-acetonitrile, under laboratory conditions, allows us to reach yields higher than 90%, optimizing the purification steps and without the use of extreme conditions (inert atmosphere, high temperatures or corrosive agents). All compounds were characterized by the use of spectroscopic techniques. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Effects of N-(Alkoxyphenyl)-1-hydroxynaphthalene-2-carboxamides on Intestinal Microbial Communities

by Vanina Nikolaeva, Tomas Gonec, Ivan Kushkevych and Josef Jampilek

Chem. Proc. 2023, 14(1), 45; https://doi.org/10.3390/ecsoc-27-16142 - 15 Nov 2023

Viewed by 264

Abstract

The phylum Proteobacteria, more precisely, the family Enterobacteriaceae, has been shown to be a major cause of inflammation in the human microbiome. Their standard level in the human intestine is usually kept below 1% in a healthy person, and their overgrowth above [...] Read more.

The phylum Proteobacteria, more precisely, the family Enterobacteriaceae, has been shown to be a major cause of inflammation in the human microbiome. Their standard level in the human intestine is usually kept below 1% in a healthy person, and their overgrowth above this number leads to intestinal inflammation, which can cause the development of inflammatory bowel diseases, most often, Crohn’s disease or ulcerative colitis. The minimum inhibitory concentrations (MICs) of a series of eighteen recently synthesized N-(alkoxyphenyl)-2-hydroxynaphthalene-1-carboxamides were determined against two representatives of the Enterobacteriaceae family–Escherichia coli CCM 3954 and Salmonella typhimurium LT 2-18. Although the tested compounds are cyclic analogues of salicylanilides known to have strong antimicrobial properties, the found MICs ranged between 50 µM and 1000 µM. However, it can be concluded that S. typhimurium was generally more sensitive to the tested antimicrobial agents than E. coli. N-[2-(But-2-yloxy)phenyl]-1-hydroxynaphthalene-2-carboxamide was the most active agent among the investigated compounds with an MIC of 100 µM against E. coli and an MIC of 50 µM against S. typhimurium. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Aldehyde Phenylamino-Pyrimidine as Key Precursor for the Synthesis of Imatinib Analogs and In Silico Studies of Their Intermediates

by Luz E. Tierrablanca-Arias, Hugo Cervantes-Valencia, Mitzi N. Piña-Gordillo, Luis Chacón-García, Abel Suárez-Castro and Carlos J. Cortes-García

Chem. Proc. 2023, 14(1), 46; https://doi.org/10.3390/ecsoc-27-16108 - 15 Nov 2023

Viewed by 284

Abstract

The synthesis of aldehyde-PAP as a key precursor through a triple reaction sequence: diazotization-addition/CuAAC/oxidation by using 4-methyl-N³-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine as the starting material is described. Furthermore, a molecular docking study was conducted to assess the potential of these compounds as possible ABL [...] Read more.

The synthesis of aldehyde-PAP as a key precursor through a triple reaction sequence: diazotization-addition/CuAAC/oxidation by using 4-methyl-N³-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine as the starting material is described. Furthermore, a molecular docking study was conducted to assess the potential of these compounds as possible ABL kinase inhibitors. Finally, leveraging our in silico investigations, we introduce a small virtual library of compound Imatinib analogs, which will aid in identifying the optimal candidates for further in vitro experimentation. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Insights on the Interaction between Kefiran and Whey Proteins Using Computational Analyses

by Carlos Jiménez-Pérez, Laura Roldán-Hernández, Alma Cruz-Guerrero, John F. Trant and Sergio Alatorre-Santamaría

Chem. Proc. 2023, 14(1), 47; https://doi.org/10.3390/ecsoc-27-16128 - 15 Nov 2023

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Abstract

Kefiran is an exopolysaccharide produced by milk fermentation that is widely used in the food industry, mainly to improve the rheological properties of foods, as well as for the formation of biofilms. Most of these properties are related to its interaction with milk [...] Read more.

Kefiran is an exopolysaccharide produced by milk fermentation that is widely used in the food industry, mainly to improve the rheological properties of foods, as well as for the formation of biofilms. Most of these properties are related to its interaction with milk proteins. It has been reported that kefiran has a molecular weight of up to 10⁷ Da and that it is formed by glucose and galactose molecules in equimolar quantities; however, its folding form is not completely understood. In this work it was elucidated that a model of the 20 kDa kefiran folds in a helical shape. In addition, it was determined that whey proteins can form complexes with kefiran. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Trisubstituted 1,3,5-Triazines and Their Effect on BACE1

by Petra Majerova, Ivana Gerhardtova, Eva Havrankova, Timotej Jankech, Andrej Kovac and Josef Jampilek

Chem. Proc. 2023, 14(1), 48; https://doi.org/10.3390/ecsoc-27-16111 - 15 Nov 2023

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Abstract

Alzheimer’s disease (AD) is a multifactorial neurological disease of unknown etiology that is associated with various risk factors. Various pharmacological approaches targeting distinct mechanisms have been investigated; however, they have not yet achieved disease-modifying effects. A series of nine trisubstituted 1,3,5-triazine-based derivatives was [...] Read more.

Alzheimer’s disease (AD) is a multifactorial neurological disease of unknown etiology that is associated with various risk factors. Various pharmacological approaches targeting distinct mechanisms have been investigated; however, they have not yet achieved disease-modifying effects. A series of nine trisubstituted 1,3,5-triazine-based derivatives was investigated as potential inhibitors of the β-secretase enzyme (beta-site amyloid precursor protein-cleaving enzyme 1, BACE1), one of the key enzymes in the pathogenesis of AD. Although the triazine-based derivatives are reported to be potent BACE1 inhibitors, the compounds discussed in this contribution, at a concentration of 10 µM, demonstrated completely insignificant activity. It is worth noting that methyl (4-{4-[(2,3-dihydroxypropyl)amino]-6-[(4-sulfamoylbenzyl)amino]-1,3,5-triazin-2-yl}piperazin-1-yl)- acetate and 4-({4-chloro-6-[(3-hydroxypropyl)amino]-1,3,5-triazin-2-yl}amino)benzenesulfonamide showed an approximately 9% and 2% inhibition of BACE1 activity, respectively. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Phenothiazine Conjugate with Mitochondria-Directed Cationic Compound F16: Synthesis and Cytotoxic Action against Human Breast Carcinoma

by Eldar Davletshin, Darya Nedopekina, Rezeda Khalitova, Mikhail Dubinin, Konstantin Belosludtsev and Anna Spivak

Chem. Proc. 2023, 14(1), 49; https://doi.org/10.3390/ecsoc-27-16120 - 15 Nov 2023

Viewed by 414

Abstract

The development of new drugs or drug candidates based on the phenothiazine system (10H-dibenzo-[b,e]-1,4-thiazine) is a promising approach in view of the diverse biological activity of this tricyclic system, which is present in traditional drugs (chlorpromazine, thioridazine, trifluoperazine, and trifluopromazine) with antipsychotropic, antihistamine [...] Read more.

The development of new drugs or drug candidates based on the phenothiazine system (10H-dibenzo-[b,e]-1,4-thiazine) is a promising approach in view of the diverse biological activity of this tricyclic system, which is present in traditional drugs (chlorpromazine, thioridazine, trifluoperazine, and trifluopromazine) with antipsychotropic, antihistamine and antimuscarinic activities. In practical medicine, these drugs are used as antagonists of dopamine and other neurotransmitter receptors for the treatment of schizophrenia and bipolar disorders. Ongoing studies on the synthesis and biological screening of various phenothiazine derivatives in recent years have revealed other important biological effects of these compounds, among which their antitumor effects are of great interest. This work reports the synthesis of a novel N-substituted phenothiazine analog bearing a mitochondria-directed cationic group (E)-4-(1H-indol-3-ylvinyl)-pyridinium (F16) linked to the nitrogen atom of the phenothiazine core by a butane bridge. The lipophilic cationic F16 fragment was used as a means to enhance transmembrane transport and selective delivery of the hybrid molecule into the mitochondria of cancer cells. In tests on the BT474 breast cancer cell line, the phenothiazine-F16 hybrid demonstrated significant cytotoxic activity. The cytotoxic effect of the compound was noticeable at a concentration of 5 μM and further increased dose-dependently, leading to complete tumor cell death at a concentration of 50 μM (IC₅₀ 3.3 μM). The F16-derivative of phenotzine showed marked mitochondrial targeting. In experiments on isolated rat liver mitochondria, the tested agent, already at a concentration of 5 μM, significantly decreased the membrane potential of succinate-energized organelles. Increasing the concentration of the phenothiazine hybrid to 20 μM resulted in complete dissipation of the potential. The obtained result of antitumor activity against BT-474 cell culture and significant effect on the reduction of mitochondrial membrane potential allows us to consider phenothiazine-F16 hybrid as a new promising antitumor drug. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Synthesis and Evaluation of Thiomethyl-Substituted (4Z)-4-[(Pyrazol-4-yl)methylene]pyrazolone as an Optical Chemosensor

by Paola V. Mazón Ayala, Juan Carlos Romero-Benavides and Jorge Heredia-Moya

Chem. Proc. 2023, 14(1), 50; https://doi.org/10.3390/ecsoc-27-16123 - 15 Nov 2023

Viewed by 348

Abstract

Developing colorimetric devices for detecting chemical species is essential in many fields; nevertheless, developing effective chemosensors for many heavy and transition metal ions remains an important issue. As a result, in recent years, the use of colorimetric sensors for the selective and sensitive [...] Read more.

Developing colorimetric devices for detecting chemical species is essential in many fields; nevertheless, developing effective chemosensors for many heavy and transition metal ions remains an important issue. As a result, in recent years, the use of colorimetric sensors for the selective and sensitive detection of metal ions has grown in popularity. Pyrazolones and their derivatives are heterocyclic compounds that have attracted interest due to their biological and pharmacological features. As a result, they have been used in various areas, including agriculture, medicine, organic synthesis, and analytical chemistry. However, the potential for chemosensing has yet to receive much attention. In this study, thiomethyl-substituted (4Z)-4-[(pyrazol-4-yl)methylene]pyrazolone was synthesized, and its ability to act as an optical chemosensor for several metals was evaluated. According to preliminary results, this molecule could be an optical chemosensor to detect Fe³⁺, Sn²⁺, and Al³⁺. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Molecular Modelling and In Vitro Research of New Substances for the Targeted Stimulation of AQP3 in Skin

by Viktor Filatov, Andrey Varava and Egor Ilin

Chem. Proc. 2023, 14(1), 51; https://doi.org/10.3390/ecsoc-27-16088 - 15 Nov 2023

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Abstract

Skin dryness and xerosis are the most common clinical manifestations of different dermatological diseases. At the same time, it was established that the expression of aquaporin 3 (AQP3) is related to the pathogenesis of atopic dermatitis, psoriasis, eczema, and vitiligo. Thus, our study [...] Read more.

Skin dryness and xerosis are the most common clinical manifestations of different dermatological diseases. At the same time, it was established that the expression of aquaporin 3 (AQP3) is related to the pathogenesis of atopic dermatitis, psoriasis, eczema, and vitiligo. Thus, our study was focused on the search for new molecules and the investigation of their biological activity to accelerate the expression of AQP3 in the skin’s epidermis. Aloin from an Aloe barbadensis leaf extract and trimethylglycine were chosen as new potential candidates using DiffDock computational modelling. These natural molecules demonstrated a good affinity towards the active site of AQP3 with an estimated docking score of −6.2 kcal/mol to −7.7 kcal/mol. Phyto4Health modelling predicted the anti-psoriatic, anti-inflammatory, and immunosuppressant activities that are useful in the treatment of atopic skin diseases. Furthermore, it was shown that the combination of the Aloe barbadensis leaf extract and trimethylglycine in a mass ratio of 1:1 revealed a clear synergetic effect to increase the AQP3 amount up to two times. Thus, the combination of the Aloe barbadensis extract standardized for aloin and trimethylglycine has a promising potential in drug development and the treatment of dryness. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

A Robust Regression-Based Modeling to Predict Antiplasmodial Activity of Thiazolyl–Pyrimidine Hybrid Derivatives against Plasmodium falciparum

by Kevin S. Umoette, Charles O. Nnadi and Wilfred O. Obonga

Chem. Proc. 2023, 14(1), 52; https://doi.org/10.3390/ecsoc-27-16167 - 15 Nov 2023

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Abstract

Thiazolyl–pyrimidine hybrid plays significant roles in the biological activities and SAR of thiazolylpyrimidines (Tzpd), thiazolopyrimidines, and thienopyrimidines due to the combination of the thiazole and pyrimidine pharmacophores. The study developed regression-based models for the prediction of antiplasmodial activity of 43 Tzpd hybrid obtained [...] Read more.

Thiazolyl–pyrimidine hybrid plays significant roles in the biological activities and SAR of thiazolylpyrimidines (Tzpd), thiazolopyrimidines, and thienopyrimidines due to the combination of the thiazole and pyrimidine pharmacophores. The study developed regression-based models for the prediction of antiplasmodial activity of 43 Tzpd hybrid obtained from the ChEMBL database. The molecular descriptors (145 features) were scaled down to 6 using the recursive feature elimination. The X- and Y-matrix were split into 34 train and 9 test sets using a split ratio of 0.20. Regression models were built using scikit-learn algorithms: multiple linear regression (MLR), k-Nearest Neighbors (kNN), Support Vector Regressor (SVR), and Random Forest Regressor (RFR) to predict the pIC₅₀ of the test set. The models were evaluated using R², mean squared error (MSE), mean absolute error (MAE), root mean squared error (RMSE), p-values, F-statistic, and variance inflation factor (VIF). Of the 145 features calculated for the 43 Tzpd, 6 molecular features, FCASA-, MNDO_LUMO, E_str, vsurf_HB1, vsurf_G, and vsurf_DD12 (p < 0.05; VIF < 5), were found to significantly influence the antiplasmodial activity. Fivefold cross-validation performance scores of MLR, kNN, SVR, and RFR showed that the performance metrics of MLR (MSE = 0.1453; R² = 0.680; MAE = 0.290; RMSE = 0.381; pIC₅₀(predicted) = 8.06 − 0.45vsurf_G + 0.37FCASA- − 0.42MNDO_LUMO − 0.20E_str + 0.30vsurf_HB1 − 0.38vsurf_DD12) outperformed other models. The study developed predictive models and provided insights into the chemical features necessary for the optimization of thiazolyl–pyrimidine to enhance antiplasmodial activity. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

GC-MS Analysis of Defensive Secretions of a Cuban Endemic Millipede of the Genus Rhinocricus—Chemical Prospecting of Neotropical Biodiversity

by Juan Enrique Tacoronte Morales, Carla Bernal Villavicencio, Xavier Leopoldo Gracia Cervantes, Maria Elizabeth Canchingre and Maria Teresa Cabrera Pedroso

Chem. Proc. 2023, 14(1), 53; https://doi.org/10.3390/ecsoc-27-16077 - 15 Nov 2023

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Abstract

The poly-component composition of repugnatorial secretions isolated from Rhinocricus duvernoyi Kasrh 1981 eco-geographical populations, inhabiting in the eastern zone of Cuban archipelago, was analyzed using GC-MS. Were identified several benzoquinonoids and related derivatives, revealing the existence of a singular compositional heterogeneity at a [...] Read more.

The poly-component composition of repugnatorial secretions isolated from Rhinocricus duvernoyi Kasrh 1981 eco-geographical populations, inhabiting in the eastern zone of Cuban archipelago, was analyzed using GC-MS. Were identified several benzoquinonoids and related derivatives, revealing the existence of a singular compositional heterogeneity at a geographical scale. The preliminary molecular-geographic mapping of the Cuban archipelago detailed the presence of 3 chemotypes in the east region. The work reports a structural-chromatographic molecular database containing the components of defensive secretions. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 3851 KiB

Open AccessProceeding Paper

^99mTc-Selenium-NPs as SPECT Tracers: Radio Synthesis and Biological Evaluation

by Akhilesh Kumar Singh, Mohd. Faheem, Amit Jaiswal, Malleswari Ponnala, Sanjay Gambhir and Manish Dixit

Chem. Proc. 2023, 14(1), 54; https://doi.org/10.3390/ecsoc-27-16172 - 14 Dec 2023

Viewed by 672

Abstract

As the usage of nano-sized complexes in biomedical applications has grown significantly over the past ten years, nanoparticles are now playing a significant role in the enhancement and revolution of medical applications. It may be due primarily to the novel and exceptional electrical, [...] Read more.

As the usage of nano-sized complexes in biomedical applications has grown significantly over the past ten years, nanoparticles are now playing a significant role in the enhancement and revolution of medical applications. It may be due primarily to the novel and exceptional electrical, optical, photo-responsive, and catalytic capabilities displayed by particles with sizes ranging from 1 to 100 nm. The radiolabelled nanoparticles refer to the process of incorporating radioactive isotopes into nanoparticles. This technique enables the nanoparticles to be tracked, imaged and monitored using various imaging techniques, such as Single-Photon Emission Computed Tomography (SPECT/CT) or Positron Emission Tomography (PET). They play a crucial role in understanding the biodistribution, pharmacokinetics, and targeted delivery of nanoparticles to biological systems. In this study, selenium-based nanoparticles (Se-NPs) were explored for imaging potential as these are usable due to their size, surface, and kinetics, as well as their ability to be functionalised. The ^99mTechnicium (^99mTc) radionuclide was used to radiolabel the bio-inspired highly dispersed over grown endophytic fungus Fusarium oxysporum selenium NP using conventional radiochemistry protocol. The radiolabelling yield was found to be 94.5 ± 3% and analysed by various analytical tools. The synthesized ^99mTc-Se-NPs were assessed through In-vitro stability, and their In-vivo biodistribution was performed. The accumulation of post six-hour data was primarily seen in the liver (around 3.4% ID/g) and lungs (about 2.2% ID/g). These Se-NPs can be used as an imaging agent for lung and liver disorders because these NPs quickly pass through the kidneys are expelled via urine and show a long retention time in the body. These properties of ^99mTc-Se-NPs can be used for non-invasive imaging via SPECT. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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4815 KiB

Open AccessProceeding Paper

In Silico Approaches for the Study of New Anti-Parkinson’s Agents

by Merzaka Mettai, Ismail Daoud and Nadjib Melkemi

Chem. Proc. 2023, 14(1), 55; https://doi.org/10.3390/ecsoc-27-16067 - 15 Nov 2023

Viewed by 339

Abstract

Parkinson’s disease (PD) is the second most common neurodegenerative chronic disorder in older people, caused by the loss of dopaminergic neurons in the brain, which leads to dopamine depletion. Among its symptoms are resting tremor, rigidity, and dementia. Monoamine oxidase B (MAO-B) is [...] Read more.

Parkinson’s disease (PD) is the second most common neurodegenerative chronic disorder in older people, caused by the loss of dopaminergic neurons in the brain, which leads to dopamine depletion. Among its symptoms are resting tremor, rigidity, and dementia. Monoamine oxidase B (MAO-B) is a key enzyme in PD. The inhibition of it increases the level of dopamine in the brain by preventing its degradation, especially in the early stages of the disease. In the present work, we combined molecular docking with an ADME analysis of a new class of ten derivatives of indanone in order to reduce the metabolic depletion of dopamine through inhibiting the MAO-B. A molecular docking study was performed to clarify the bonding modes and affinities between the active site residues of MAO-B with the new class derivatives of indanone, followed by the ADME prediction to check the drug-likeness properties of the best ligands obtained using the method above. Molecular docking results show that the ligands L3 and L5 presented a high negative score energy (−8.809 kcal/mol, −9.276 kcal/mol), respectively, with good RMSD values (1.419 Å, 1.560 Å), respectively. Moreover, the ADME prediction gave promising results that those ligands have an oral bioavailability and a high level of gastrointestinal absorption, which means they can be good inhibitors against Parkinson’s disease. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

New Azo Carboxylic Dyes Derived from Eugenol: Synthesis and Preliminary Application to Polyamide

by José R. A. Coelho, Maria José G. Fernandes and M. Sameiro T. Gonçalves

Chem. Proc. 2023, 14(1), 56; https://doi.org/10.3390/ecsoc-27-16044 - 15 Nov 2023

Viewed by 336

Abstract

A series of azo dyes containing eugenol, the major phenolic compound in clove (Syzygium aromaticum) essential oil, was synthesized by coupling reactions of diazonium salts of different amines based on 3-aminobenzoic acid with eugenol. The new eugenol-based azo dyes were fully [...] Read more.

A series of azo dyes containing eugenol, the major phenolic compound in clove (Syzygium aromaticum) essential oil, was synthesized by coupling reactions of diazonium salts of different amines based on 3-aminobenzoic acid with eugenol. The new eugenol-based azo dyes were fully characterized by the usual analytical techniques and used in preliminary reactive dyeing tests on polyamide fabric to determine the colour fastness and staining under domestic washing conditions. The results obtained revealed the potential of these dyes for applications in the textile area. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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2261 KiB

Open AccessProceeding Paper

Theoretical and Experimental Study of the Chemical Modification of Poly(epichlorohydrin) by Grafting Menthol

by Ratiba Hadjadj Aoul, Abdelghani Adda, Fatima Zohra Sebba and Fathallah Bousta

Chem. Proc. 2023, 14(1), 57; https://doi.org/10.3390/ecsoc-27-16148 - 15 Nov 2023

Viewed by 491

Abstract

Functional polymers, a significant class of compounds with diverse applications, are synthesized by incorporating functional groups into polymer matrices. Poly(epichlorohydrin) (PECH) is a pivotal polymer due to its reactive chloromethyl group, which readily enables its transformation into various functional polymers. Our study is [...] Read more.

Functional polymers, a significant class of compounds with diverse applications, are synthesized by incorporating functional groups into polymer matrices. Poly(epichlorohydrin) (PECH) is a pivotal polymer due to its reactive chloromethyl group, which readily enables its transformation into various functional polymers. Our study is focused on theoretically unraveling the mechanism behind modifying PECH through menthol grafting. We optimized and characterized various stationary states using density functional theory (DFT) at the B3LYP/6-311++G** level. These calculations were conducted in both the gas phase and a solution environment (THF). To anticipate the specific sites within our polymer that would be subject to grafting, we calculated various reactivity indices at the same computational level. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Synephrine Analogues as Glucocorticoid Receptor Agonists

by Eugenia Oleynik, Ekaterina Mikhina, Diana Grigoreva, Varvara Maksimova, Lyubov Grebenkina, Andrey Valerevich Matveev, Ekaterina Zhidkova, Ekaterina Lesovaya and Marianna Yakubovskaya

Chem. Proc. 2023, 14(1), 58; https://doi.org/10.3390/ecsoc-27-16152 - 15 Nov 2023

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Abstract

This work carried out the synthesis of several new synephrine analogues by universal method. Some of the synthesized compounds showed cytotoxicity on myeloid leukaemia cells K562 and lymphoma cell line Granta-519. Molecular docking using the glucocorticoid receptor (GR) model (PDB identifier 1P93) was [...] Read more.

This work carried out the synthesis of several new synephrine analogues by universal method. Some of the synthesized compounds showed cytotoxicity on myeloid leukaemia cells K562 and lymphoma cell line Granta-519. Molecular docking using the glucocorticoid receptor (GR) model (PDB identifier 1P93) was performed to understand the possible underlying mechanism of compound action. The simulation showed the similarity of synephrine analogues’ binding to the binding of dexamethasone in the GR ligand-binding domain. The synthesized analogues exhibited cytotoxicity profiles similar to those of dexamethasone. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Synthesis of Aromatic Macrodiolides and Study of Their Antitumor Activity In Vitro

by Ilgam Gaisin, Ilgiz Islamov, Lilya U. Dzhemileva and Usein Dzhemilev

Chem. Proc. 2023, 14(1), 59; https://doi.org/10.3390/ecsoc-27-16102 - 15 Nov 2023

Viewed by 258

Abstract

Based on (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid, previously undescribed polyether aromatic macrodiolides were synthesized in good yields (53–67%). The cytotoxicity of the resulting macrocyclic compounds in vitro against tumor Jurkat cells, K562 cells, conditionally normal Hek293 cell lines and normal fibroblasts was [...] Read more.

Based on (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid, previously undescribed polyether aromatic macrodiolides were synthesized in good yields (53–67%). The cytotoxicity of the resulting macrocyclic compounds in vitro against tumor Jurkat cells, K562 cells, conditionally normal Hek293 cell lines and normal fibroblasts was the assessment carried out. The ability of the most active macrodiolide to induce apoptosis toward Jurkat cells and influence the cell cycle was studied. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Theoretical Study of the Addition Reaction of Arylazides to 1,3-Dicarbonyl Compounds

by Adda Abdelghani, Halima Hadj Mokhtar, Ouda Boumaza and Abderrahmane Naous

Chem. Proc. 2023, 14(1), 60; https://doi.org/10.3390/ecsoc-27-16160 - 15 Nov 2023

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Abstract

Our research focuses on the synthesis of 1,2,3-triazoles through 1,3-dipolar cycloaddition involving arylazides. The reaction demonstrates high efficiency when conducted in the presence of morpholine, resulting in 100% regioselectivity towards a single isomer. A theoretical study of this reaction can be conducted to [...] Read more.

Our research focuses on the synthesis of 1,2,3-triazoles through 1,3-dipolar cycloaddition involving arylazides. The reaction demonstrates high efficiency when conducted in the presence of morpholine, resulting in 100% regioselectivity towards a single isomer. A theoretical study of this reaction can be conducted to gain insights into its mechanism and provide valuable information for its optimization. This study involves the use of computational methods, such as density functional theory (DFT), to calculate the structures, energies, and properties of the reactants, intermediates, transition states, and products involved in the reaction. The calculations were performed using the Gaussian09 program with the B3LYP(GD3BJ)/6-31G(d,p) method. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Oxidative Aromatization of Some 1,4-Dihydropyridine Derivatives Using Pyritic Ash in Eco-Sustainable Conditions

by Juan Enrique Tacoronte Morales, Carla Bernal Villavicencio, Xavier Leopoldo Gracia Cervantes, Maria Elizabeth Canchingre and Maria Teresa Cabrera Pedroso

Chem. Proc. 2023, 14(1), 61; https://doi.org/10.3390/ecsoc-27-16066 - 14 Nov 2023

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Abstract

Hantzsch 1,4-dihydropyridines (Hantzsch 1,4-DHP), have been utilized as starting material in organic synthesis. In addition, several 1,4-DHP based drugs (Nifedipine, Niguldipine, Amlodepine besylate) have been recognized for the treatment of cardiovascular diseases. During the redox processes, 1,4-DHP systems are oxidatively transformed into the [...] Read more.

Hantzsch 1,4-dihydropyridines (Hantzsch 1,4-DHP), have been utilized as starting material in organic synthesis. In addition, several 1,4-DHP based drugs (Nifedipine, Niguldipine, Amlodepine besylate) have been recognized for the treatment of cardiovascular diseases. During the redox processes, 1,4-DHP systems are oxidatively transformed into the corresponding pyridine derivatives. Furthermore, the oxidation of Hantzsch 1,4-DHP constitutes the more accessible method to obtain pyridine derivatives with a great spectrum of important properties. Pyritic ashes, a waste material from the metallurgical industry, has shown catalytic activity in redox processes, and its use can facilitate the obtaining of derivatives from dihydropyridines under sustainable conditions. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Microwave-Assisted Synthesis, Characterization, and Biological Activity of New Copper (II) Complex with Sulfonamide

by Rania Bahadi, Malika Berredjem, Rayenne Redjemia and Chahrazed Benzaid

Chem. Proc. 2023, 14(1), 62; https://doi.org/10.3390/ecsoc-27-16157 - 15 Nov 2023

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Abstract

A fast and efficient synthesis was carried out to obtain a new derivative of an organometallic complex. This synthesis involved the complexation of a sulfonamide derived from phenylpiperazine with copper (II). The synthesis of this complex was achieved using an innovative and environmentally [...] Read more.

A fast and efficient synthesis was carried out to obtain a new derivative of an organometallic complex. This synthesis involved the complexation of a sulfonamide derived from phenylpiperazine with copper (II). The synthesis of this complex was achieved using an innovative and environmentally friendly method that used microwave irradiation as the energy source. The resulting complex was obtained as a green powder with a yield of 82%. The identification of the final compound was performed through infrared spectroscopy, UV-Visible spectroscopy, elemental analysis, and cyclic voltammetry. The obtained complex exhibited noteworthy activity against the tested bacterial and fungal strains. Regarding the anti-inflammatory activity, the highest percentage of inhibition of BSA denaturation (0.2%) was recorded in the fraction at a concentration of 5000 ppm, which was 67.32%. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Preparation of a Fluorescent Peptide Substrate to Target Tumor-Associated Macrophages

by Ângela B. M. P. Leite, Cátia D. F. Martins, M. Manuela M. Raposo and Susana P. G. Costa

Chem. Proc. 2023, 14(1), 63; https://doi.org/10.3390/ecsoc-27-16101 - 15 Nov 2023

Viewed by 310

Abstract

One of the significant challenges in targeting M2 macrophages is the need for specific and high-affinity targeting ligands that can distinguish them from phenotype M1 macrophages. In order to investigate the selectivity of the polypeptide M2pep (YEQDPWGVKWWY) towards M2 macrophages using fluorescence-based techniques, [...] Read more.

One of the significant challenges in targeting M2 macrophages is the need for specific and high-affinity targeting ligands that can distinguish them from phenotype M1 macrophages. In order to investigate the selectivity of the polypeptide M2pep (YEQDPWGVKWWY) towards M2 macrophages using fluorescence-based techniques, we report here the synthesis and characterization of the M2pep substrate labeled with a fluorophore. This peptide comprising a 12-amino acid sequence with a spacer consisting of three additional glycines (GGG) was synthesized and coupled to Rhodamine B at its N-terminal via microwave-assisted solid-phase synthesis. The structure of the labeled peptide was confirmed by NMR, UV-Vis, fluorescence spectroscopy and mass spectrometry. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Chromo-Fluorogenic Detection of Cyanide Ion with a Cyanine Probe

by Cátia D. F. Martins, Maria Manuela M. Raposo and Susana P. G. Costa

Chem. Proc. 2023, 14(1), 64; https://doi.org/10.3390/ecsoc-27-16109 - 15 Nov 2023

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Abstract

Due to the extreme toxicity of cyanide in biological systems and its widespread presence in the environment, great efforts have been focused on developing sensitive and selective methods for cyanide detection. In this regard, sulfo-cyanine dye 1 was evaluated as a colorimetric and [...] Read more.

Due to the extreme toxicity of cyanide in biological systems and its widespread presence in the environment, great efforts have been focused on developing sensitive and selective methods for cyanide detection. In this regard, sulfo-cyanine dye 1 was evaluated as a colorimetric and fluorimetric probe for various anions. Chemosensing studies revealed that this compound exhibited remarkable selectivity and sensitivity for CN⁻ in acetonitrile solution, with a marked colour change from cyan to colourless and fluorescence emission switched off. The detection limit was estimated to be as low as 0.45 μM, and the binding mode was studied using NMR techniques. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Design, Synthesis, and Biological Assessment of Novel Vanillin-Isoxazole Derivatives as Positive Allosteric Modulators of α7 Nicotinic Acetylcholine Receptor

by Santiago Stabile, Juan Facundo Chrestia, Gabriel Radivoy and Cecilia Bouzat

Chem. Proc. 2023, 14(1), 65; https://doi.org/10.3390/ecsoc-27-16097 - 15 Nov 2023

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Abstract

The homomeric α7 nicotinic acetylcholine receptor (α7 nAChR) is a cation-permeable pentameric ligand-gated channel present in the nervous system and non-neuronal cells. α7 nAChRs are highly expressed in brain regions critical for cognition and memory, such as the hippocampus and cerebral cortex. Therefore, [...] Read more.

The homomeric α7 nicotinic acetylcholine receptor (α7 nAChR) is a cation-permeable pentameric ligand-gated channel present in the nervous system and non-neuronal cells. α7 nAChRs are highly expressed in brain regions critical for cognition and memory, such as the hippocampus and cerebral cortex. Therefore, enhancing its function with positive allosteric modulators (PAMs) is a promising therapeutic approach for treating cognitive deficits and neurodegenerative disorders. Continuing with our previous work in the search for novel PAMs of α7 nAChR, this study presents the synthesis and biological evaluation of novel isoxazole-vanillin derivatives exhibiting α7-PAM activity. Isoxazole derivatives with functional α7-PAM activity were identified by determining the effects of the synthetic compounds at different concentrations on the properties of the single channels elicited by ACh (100 μM). We found that only vanillin-derived isoxazoles (containing the 4-hydroxy-3-methoxy fragment) exhibited α7-enhancing activity in comparison to isoxazoles derived from dihydroxy- or dimethoxybenzaldehydes. The use of different substituted phenylacetylenes allowed us to create a small library of compounds with α7-PAM activity. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Analysis of the Chemical Composition and Evaluation of Antioxidant and Anti-Inflammatory Properties of Hydrosol Extract and Its Principal Component (Carlina Oxide) in Aerial Parts of Atractylis gummifera from Western Algeria

by Tabet Zatla Amina, Hammoudi Amina and Brikci Nigassa Nawel

Chem. Proc. 2023, 14(1), 66; https://doi.org/10.3390/ecsoc-27-16135 - 15 Nov 2023

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Abstract

This work aimed to determine the chemical composition of hydrosol extract from Atractylis gummifera and to assess the in vitro antioxidant and anti-inflammatory properties of this extract, as well as analyze the carlina oxide isolated from it. This study also examined the in [...] Read more.

This work aimed to determine the chemical composition of hydrosol extract from Atractylis gummifera and to assess the in vitro antioxidant and anti-inflammatory properties of this extract, as well as analyze the carlina oxide isolated from it. This study also examined the in vitro synergistic effect of carlina oxide with BHT and diclofenac to reduce their minimum effective doses and minimize their potential side effects. The primary component of the hydrosol extract from A. gummifera was identified as the acetylenic compound carlina oxide (79.1%), which was isolated and confirmed through spectroscopic techniques such as ¹H NMR, ¹³C NMR, and IR. The results of the biological assays demonstrated that both the hydrosol extract and carlina oxide exhibited noteworthy antioxidant and anti-inflammatory properties. Additionally, combining carlina oxide with positive controls yielded the enhancement of these activities, resulting in a significant reduction in the inhibitory concentrations and doses of the synthetic antioxidants and anti-inflammatories. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Hexa-Substituted Hybrid C₆₀ Derivatives with Norbornadiene Fragments: Synthesis and Structure

by Arslan R. Akhmetov, Zarema R. Sadretdinova, Arthur R. Tulyabaev and Leonard M. Khalilov

Chem. Proc. 2023, 14(1), 67; https://doi.org/10.3390/ecsoc-27-16104 - 15 Nov 2023

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Abstract

New hybrid fullerene C₆₀ derivatives with five norbornadiene fragments, at a distance from the fullerene core of several methylene groups, were synthesized for the first time. Subsequent photoirradiation of these derivatives leads to only partial (up to 20%) opening of double bonds [...] Read more.

New hybrid fullerene C₆₀ derivatives with five norbornadiene fragments, at a distance from the fullerene core of several methylene groups, were synthesized for the first time. Subsequent photoirradiation of these derivatives leads to only partial (up to 20%) opening of double bonds in norbornadiene fragments to form quadricyclane substituents. It is assumed that the resulting fullerene C₆₀ derivatives can serve as a basis to create high-energy materials. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Synthesis of C₆₀ Fullerene Hexakis Adducts Based on Strained Polycyclic Hydrocarbons and Their Application in Organic Electronics

by Arslan R. Akhmetov, Rishat I. Aminov, Zarema R. Sadretdinova, Renat B. Salikhov, Ilnur N. Mullagaliev and Timur R. Salikhov

Chem. Proc. 2023, 14(1), 68; https://doi.org/10.3390/ecsoc-27-16147 - 15 Nov 2023

Viewed by 218

Abstract

Using the Bingel–Hirsch reaction, new hexakis methanofullerenes containing strained polycyclic hydrocarbons were synthesized. Organic field-effect transistors were manufactured based on the obtained compounds. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Antibacterial Action, Antioxidant Activity and Anticoagulant Effect of Pectin Extracted from Peels of Algerian Citrus Sinensis

by Nacer Boudouaia, Ahmed Amine Bendaoudi, Samir Benykhlef, Zohra Bengharez and Andres Cantarero

Chem. Proc. 2023, 14(1), 69; https://doi.org/10.3390/ecsoc-27-16069 - 15 Nov 2023

Viewed by 391

Abstract

In this study, we characterised the pectin extracted from peels of Algerian Citrus sinensis and evaluated its antibacterial action, antioxidant activity and anticoagulant effect. Pectin was extracted under acidic conditions using hydrochloric acid for PCT-1 and citric acid for PCT-2 and determining their [...] Read more.

In this study, we characterised the pectin extracted from peels of Algerian Citrus sinensis and evaluated its antibacterial action, antioxidant activity and anticoagulant effect. Pectin was extracted under acidic conditions using hydrochloric acid for PCT-1 and citric acid for PCT-2 and determining their physicochemical properties using Fourier-Transform Infrared spectroscopy (FTIR), X-ray powder diffraction (PXRD), differential scanning calorimetry (DSC), yield, the degree of methylation, water content and ash content. In addition, the FTIR results showed desired banding characteristics, and their thermal properties evaluated using DSC showed that the thermal degradation was around 240 °C. XRD results show that PCT-1 and PCT-2 are amorphous and have similar characteristics to commercial pectin. On the other hand, the antibacterial action showed that PCT-1 and PCT-2 have no effect on Pseudomonas aeruginosa and E. coli bacteria, unlike Staphylococcus epidermidis, where it showed considerable antibacterial action. The antioxidant activity of PCT-1 and PCT-2 was observed using the 2,2 diphenyl-1-picrylhydrazyl (DPPH) method; the absorbance values recorded for PCT-1 and PCT-2 confirmed their antioxidant potential explained by the presence of several free hydroxyl groups in the PCT-1 and PCT-2 structure. On the other hand, our findings indicate that PCT-1 and PCT-2 do not have a marked anticoagulant effect but have acceptable potential and can be used as anticoagulants for the treatment of thrombotic diseases with fewer side effects compared to the widely used heparin. These results suggest that pectin from the peels of Algerian Citrus sinensis has potential properties as a biomaterial for several biomedical applications. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Synthesis of New Unsaturated Polyether Macrodiolides Based on (7Z,11Z)-Octadeca-7,11-Diene-1,18-Dioic Acid

by Ilgiz Islamov, Ilgam Gaisin and Usein Dzhemilev

Chem. Proc. 2023, 14(1), 70; https://doi.org/10.3390/ecsoc-27-16047 - 15 Nov 2023

Viewed by 240

Abstract

Stereoselective synthesis of (7Z,11Z)-octadeca-7,11-diene-1,18-dioic acid was carried out using a homo-cyclomagnesiation reaction of 2-(nona-7,8-dien-1-yloxy)tetrahydro-2H-pyran. After Steglisch esterification of the synthesized acid and polyester acetylenes in the presence of DCC and DMAP, the corresponding diesters were synthesized in [...] Read more.

Stereoselective synthesis of (7Z,11Z)-octadeca-7,11-diene-1,18-dioic acid was carried out using a homo-cyclomagnesiation reaction of 2-(nona-7,8-dien-1-yloxy)tetrahydro-2H-pyran. After Steglisch esterification of the synthesized acid and polyester acetylenes in the presence of DCC and DMAP, the corresponding diesters were synthesized in good yields (67–75%). Based on symmetric diesters with terminal triple bonds, polyether macrodiolides containing conjugated triple bonds and pharmacophoric cis,cis-1,5-diene fragments in their structure were synthesized for the first time. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Investigating the Photophysical Properties and Biological Efficacy of BODIPY Derivatives as Photosensitizers in Photodynamic Therapy

by Raquel C. R. Gonçalves, Sónia C. S. Pinto, João Pina, Lígia C. Gomes-da-Silva, Susana P. G. Costa and M. Manuela M. Raposo

Chem. Proc. 2023, 14(1), 71; https://doi.org/10.3390/ecsoc-27-16094 - 15 Nov 2023

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Abstract

The selectivity of photosensitizers for light activation is a key advantage in photodynamic therapy (PDT), allowing for precise targeting while sparing healthy cells. Boron-dipyrromethene (BODIPY)derivatives have emerged as promising PDT candidates due to their tunable photophysical properties and versatile synthesis. Herein, we explore [...] Read more.

The selectivity of photosensitizers for light activation is a key advantage in photodynamic therapy (PDT), allowing for precise targeting while sparing healthy cells. Boron-dipyrromethene (BODIPY)derivatives have emerged as promising PDT candidates due to their tunable photophysical properties and versatile synthesis. Herein, we explore the photophysical characterization and the in vitro photodynamic activity of BODIPY analogues meso-substituted with an anthracene moiety and functionalized with iodine atoms or formyl group at the 2,6-position. The formylated anthracene–BODIPY derivative exhibited the highest phototoxicity in 4T1 breast cancer cells, making it a potential candidate for a PDT photosensitizer. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Synthesis and Complexing Ability of a New Type of Molecular Clips Based on Diaza-18-crown-6 or Diamino-Dibenzo-18-crown-6 with Pendant p-tert-butylcalix[4]arenes

by Ekaterina Kulygina, Elena Alekseeva, Il’dar Rakipov and Tatiana Kirichenko

Chem. Proc. 2023, 14(1), 72; https://doi.org/10.3390/ecsoc-27-16129 - 15 Nov 2023

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Abstract

A convenient method for obtaining a new type of molecular clips based on diazacrown or diamino-dibenzocrown ethers with two calixarene molecules attached to a central fragment using an amide bond was developed. Clip 1, based on diaza-18-crown-6, demonstrates exceptional selectivity toward barium [...] Read more.

A convenient method for obtaining a new type of molecular clips based on diazacrown or diamino-dibenzocrown ethers with two calixarene molecules attached to a central fragment using an amide bond was developed. Clip 1, based on diaza-18-crown-6, demonstrates exceptional selectivity toward barium in the alkaline earth metal series and forms 2:1 (L:M) complexes with copper and iron cations. With sodium and magnesium cations, clip 2, based on diamido-dibenzo-18-crown-6, forms 1:2 (L:M) complexes. The same compound interacts with cations of copper, iron, and cadmium to form 1:1 complexes with low stability constant values. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Extraction and Complexing Abilities of a Series of p-Tert-butylcalix[4]arenes Substituted by N-carbonylmonoaza-12-crown-4

by Elena Alekseeva, Ekaterina Kulygina and Tatiana Kirichenko

Chem. Proc. 2023, 14(1), 73; https://doi.org/10.3390/ecsoc-27-1611 - 15 Nov 2023

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Abstract

The extraction and complexing properties of a series of p-tert-butylcalix[4]arene derivatives containing N-methoxycarbonylmonoaza-12-crown-4 as the substituents were evaluated using liquid–liquid extraction and spectrophotometric titration methods. It has been demonstrated that monosubstituted calixarene is an effective and highly selective extractant toward sodium cations. Both [...] Read more.

The extraction and complexing properties of a series of p-tert-butylcalix[4]arene derivatives containing N-methoxycarbonylmonoaza-12-crown-4 as the substituents were evaluated using liquid–liquid extraction and spectrophotometric titration methods. It has been demonstrated that monosubstituted calixarene is an effective and highly selective extractant toward sodium cations. Both tri- and tetrasubstituted calixarenes form mononuclear complexes with sodium cations and complexes of 1:1 and 1:2 compositions (L–M) with barium and strontium cations. The ability of calix[4]arene with four crown ether substituents to form binuclear complexes with cations of transition metals—copper, nickel, cobalt and cadmium—has also been demonstrated. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Thiohydrazides in the Synthesis of Functionalized Extranuclear Heterosteroids

by Yulia Volkova, Alexander Scherbakov and Igor Zavarzin

Chem. Proc. 2023, 14(1), 74; https://doi.org/10.3390/ecsoc-27-16179 - 15 Nov 2023

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Abstract

Heterocyclic derivatives of hormones have attracted great interest as a privileged scaffold for drug discovery due to their outstanding biological activity. A number of them are potent anticancer agents which are used in the chemotherapy of breast and prostate cancers. Here, the data [...] Read more.

Heterocyclic derivatives of hormones have attracted great interest as a privileged scaffold for drug discovery due to their outstanding biological activity. A number of them are potent anticancer agents which are used in the chemotherapy of breast and prostate cancers. Here, the data obtained by the authors in the field of studying functionalized thiohydrazides as simple “versatile agents” for the installation of heterocyclic moiety to the steroid core are summarized. Namely, a flexible synthetic approach to unknown pyrazolines, 1,3,4-thiadiazole, thiadiazine, and pyridazine derivatives of steroids with selective control of heterocyclization patterns are discussed. Steroidal 1,3,4-thiadiazoles were obtained via the oxidative heterocyclization of oxamic acid thiohydrazides with 16-hydroxymethylidene-∆^1,3,5(10)-estratrieno-17-one. An extension of this reaction to steroidal α,β-unsaturated ketones resulted in androst-5-ene-[17,16d]-pyrazolines. Spiro-androstene-17,6′[1′,3′,4′]thiadiazines were exclusively synthesized employing 16β,17β-epoxypregnenolone. Using 21-bromopregna-5,16-dien-20-one as a substrate, 17-[1′,3′,4′]thiadiazine-substituted androstenes were prepared. 18-Nor-5α-androsta-2,13-diene[3,2-d]pyridazines, androsta-2-ene[3,2-d]pyridazines and ∆^1,3,5(10)-estratrieno[16,17-d]pyridazines were synthesized via two steps involving the Vilsmeier–Haack reaction of enolizable steroidal ketones, giving chlorovinyl aldehydes, followed by the imination of the former with oxamic acid thiohydrazides. The antiproliferative activity of the synthesized compounds against breast and prostate cancer cell lines, along with lead compounds’ in-depth characterization, are included. The lead compounds were found to have potent selectivity and, in some cases, a significant effect on the signaling pathways in parental and 4-hydroxytamoxifen-resistant cells. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

In Vitro Biodegradability of Phosphorylated Hyaluronic Acid by Testicular Hyaluronidase

by Elvira A. Khaybrakhmanova, Stanislav V. Kozyrev and Irina Yu. Ponedel’kina

Chem. Proc. 2023, 14(1), 75; https://doi.org/10.3390/ecsoc-27-16107 - 15 Nov 2023

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Abstract

One of the most important characteristics for the development of biomaterials based on hyaluronic acid (HA) and its chemically modified derivatives is resistance to hyaluronidases (HA-ase), which are responsible for the degradation of HA macromolecules. In this work, samples of phosphorylated (HA-P) low- [...] Read more.

One of the most important characteristics for the development of biomaterials based on hyaluronic acid (HA) and its chemically modified derivatives is resistance to hyaluronidases (HA-ase), which are responsible for the degradation of HA macromolecules. In this work, samples of phosphorylated (HA-P) low- and high-molecular-weight HA (43 kDa and 0.5–0.7 MDa) were obtained by conventional stirring of HA/P₂O₅ mixtures at different molar ratios (1:0.2, 1:0.5, 1:1, and 1:2) and exposed to bovine testicular HA-ase (60 or 600 ME/mL, [HA] = 4 mg/mL of citrate buffer, pH 6.3, 16–18 h). It was found that the biodegradability of the HA-P samples obtained at the ratio of 1:0.2, 1: 0.5, and 1:1 was at the level of native HA or higher. Only samples obtained at a HA/P₂O₅ ratio of 1:2 showed resistance to HA-ase; their biodegradability was 13–54% lower compared to that of native HA. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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Open AccessProceeding Paper

Innovative Approaches in Acyl Sonogashira Coupling: Impact of Supported CuNPs and Cu-PdNPs Nanocatalysts

by Santiago Stabile and Gabriel Radivoy

Chem. Proc. 2023, 14(1), 76; https://doi.org/10.3390/ecsoc-27-16090 - 15 Nov 2023

Viewed by 323

Abstract

In this work, we present our findings on the acyl Sonogashira coupling catalyzed by copper nanoparticles (CuNPs) or bimetallic copper–palladium (4:1 molar ratio) nanoparticles (Cu-PdNPs) immobilized in various inorganic materials. Both catalysts allowed the synthesis of ynones in good to excellent yields. Cu-PdNPs [...] Read more.

In this work, we present our findings on the acyl Sonogashira coupling catalyzed by copper nanoparticles (CuNPs) or bimetallic copper–palladium (4:1 molar ratio) nanoparticles (Cu-PdNPs) immobilized in various inorganic materials. Both catalysts allowed the synthesis of ynones in good to excellent yields. Cu-PdNPs supported on Celite exhibit high activity, allowing reactions to proceed at room temperature, whereas the monometallic CuNPs catalysts required reactions to be carried out at 80 °C. In addition, Cu-PdNPs/Celite can be also used in Sonogashira coupling reactions with iodoarenes. Both types of catalysts can be reused without any pre-treatment after separation from the reaction medium and subsequent washing. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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934 KiB

Open AccessProceeding Paper

Study of Acetylcholinesterase and Butyrylcholinesterase (AChE/BuChE) Inhibition Using Molecular Modelling Methods

by Ferdaous Hasni, Ismail Daoud and Nadjib Melkemi

Chem. Proc. 2023, 14(1), 77; https://doi.org/10.3390/ecsoc-27-16075 - 15 Nov 2023

Viewed by 261

Abstract

Alzheimer’s disease (AD) is a neurodegenerative disease that affects the majority of people worldwide. To date, there is no cure for the disease, so new therapeutic targets need to be identified and studied. Acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) are promising therapeutic targets for [...] Read more.

Alzheimer’s disease (AD) is a neurodegenerative disease that affects the majority of people worldwide. To date, there is no cure for the disease, so new therapeutic targets need to be identified and studied. Acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) are promising therapeutic targets for AD treatment. In order to identify new inhibitors, a newly synthesized series containing thirty seven 2-hydroxy-N-phenylbenzamidederivatives were tested to study the inhibition of enzymes associated with this disease. Our work focuses on the use of molecular modeling methods based on molecular docking, QSAR and ADME property prediction. Our molecular docking results discussion is based on a number of parameters. Analysis of these obtained results showed that the ligands L18, L17 and L6 have a high inhibitory effect in the case of the enzyme AChE, while the ligands L6′, L30′ and L4′ have a high inhibitory effect in the case of the enzyme BuChE. In addition, the ADME-T properties calculation proved that these ligands respect the Lipinski, Veber and Egan rules, allowing us to select them as being probably the best inhibitors of Alzheimer’s disease (AD). Then, a QSAR model was developed to explain and predict the inhibitory activity of a series of compounds using different descriptors. This model has been validated by two methods: internal and external. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1338 KiB

Open AccessProceeding Paper

Extraction and Composition of Lipids from Pomegranate Seed Oil from West Algeria

by Salima Dib, Bachir Mostefa-Kara and Didier Villemin

Chem. Proc. 2023, 14(1), 78; https://doi.org/10.3390/ecsoc-27-16115 - 15 Nov 2023

Viewed by 332

Abstract

The beneficial health effects of pomegranate have consistently garnered scientific interest. This study delves into the health-promoting qualities of pomegranate seed oil from northwest Algeria, renowned for its nutraceutical benefits. Through Soxhlet extractions, oil yields between 11% and 17% were achieved, dependent on [...] Read more.

The beneficial health effects of pomegranate have consistently garnered scientific interest. This study delves into the health-promoting qualities of pomegranate seed oil from northwest Algeria, renowned for its nutraceutical benefits. Through Soxhlet extractions, oil yields between 11% and 17% were achieved, dependent on the chosen solvent. The oil's quality was rigorously assessed using indicators like iodine, acid, and saponification indices. Gas chromatography identified the predominance of unsaturated fatty acids (comprising 95% of the total), with a notable presence of punicic acid at 83.20%. This exceptionally high punicic acid content establishes Beni-Snouss pomegranate seed oil as a global punicic acid treasure trove, underscoring its significance as a valuable nutraceutical resource. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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758 KiB

Open AccessProceeding Paper

The Semi-Synthesis of Imidazo-5α-Hydroxyvouacapane from Caesalpinia pulcherrima via a Groebke–Blackburn–Bienaymé Reaction

by Gabriela Servín-García, América A. Frías-López, Luis Chacón-García, Mario A. Gómez-Hurtado, Gabriela Rodríguez-García, Rosa E. del Río and Carlos J. Cortés-García

Chem. Proc. 2023, 14(1), 79; https://doi.org/10.3390/ecsoc-27-16127 - 15 Nov 2023

Viewed by 265

Abstract

A semi-synthetic strategy and a new operationally simple-to-obtain heterocyclic system, imidazo-5α-hydroxyvouacapane, was developed in two-step reactions. The first reaction step is a Vilsmeier–Haack formylation at the furan ring of the 5α-hydroxyvouacapane isolated from Caesalpinia pulcherrima stems to obtain the 5α-hydroxyvouacapane-aldehyde in 33% yield. The [...] Read more.

A semi-synthetic strategy and a new operationally simple-to-obtain heterocyclic system, imidazo-5α-hydroxyvouacapane, was developed in two-step reactions. The first reaction step is a Vilsmeier–Haack formylation at the furan ring of the 5α-hydroxyvouacapane isolated from Caesalpinia pulcherrima stems to obtain the 5α-hydroxyvouacapane-aldehyde in 33% yield. The second reaction step is a Groebke–Blackburn–Bienaymé reaction to synthesize the imidazo-5α-hydroxyvouacapane by using 2-aminopyridine and tert-butyl isocyanide in 75% yield. This work contributes significantly to research on semi-synthesis through multicomponent reactions, an area with limited coverage in the literature. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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2790 KiB

Open AccessProceeding Paper

Effect and Spectroscopic Analysis of Solutions in Trychloratsetylpyrogallol Synthesis

by Ruzimurod Sattorovich Jurayev, Azimjon Uralovich Choriev and Navruz Toyirovich Qaxxorov

Chem. Proc. 2023, 14(1), 80; https://doi.org/10.3390/ecsoc-27-16180 - 15 Nov 2023

Viewed by 301

Abstract

The process of interaction of organic substances mainly occurs in solvent environments. Therefore, the effect of solvents on the o-chloroacetylation process was studied. For this, the reaction process of triatomic phenol-pyrogallol with chloroethyl chloride in various solvents was studied. In order to study [...] Read more.

The process of interaction of organic substances mainly occurs in solvent environments. Therefore, the effect of solvents on the o-chloroacetylation process was studied. For this, the reaction process of triatomic phenol-pyrogallol with chloroethyl chloride in various solvents was studied. In order to study the reaction with pyrogallol chloroacetyloride in various solvents, the compound was subjected to chromatographic, UV, IR, and NMR analyses. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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485 KiB

Open AccessProceeding Paper

A Phytochemical and Antioxidant Study of the Hexanoic Extract of Rhaponticum acaule

by Amina Hammoudi, Amina Tabet Zatla and Mohamed El Amine Dib

Chem. Proc. 2023, 14(1), 81; https://doi.org/10.3390/ecsoc-27-16141 - 15 Nov 2023

Viewed by 228

Abstract

The purpose of this work was to study the phytochemical screening and the antioxidant activity of the hexanoic extract of the root part of Rhaponticum acaule. The qualitative phytochemical analysis of the extract showed that it is composed mainly of terpenoids. The [...] Read more.

The purpose of this work was to study the phytochemical screening and the antioxidant activity of the hexanoic extract of the root part of Rhaponticum acaule. The qualitative phytochemical analysis of the extract showed that it is composed mainly of terpenoids. The result of the evaluation of the antioxidant activity revealed that the hexanoic extract is endowed with a very powerful antioxidant activity characterized by inhibitory concentrations of 50% of the free radical DPPH (IC₅₀ = 12.5 µg/mL), which is better than that of ascorbic acid (IC₅₀ = 23.5 µg/mL). In fact, these new results could lead to powerful approaches for the development of new antioxidant compounds. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1306 KiB

Open AccessProceeding Paper

Molecular Docking for the Development of Alternative Therapies against Leishmaniasis

by Juan Diego Guarimata, Christian Alcívar, Martin Lavecchia and Ana Poveda

Chem. Proc. 2023, 14(1), 82; https://doi.org/10.3390/ecsoc-27-16050 - 15 Nov 2023

Viewed by 353

Abstract

Topoisomerases play a pivotal role in regulating the topological structure of DNA during fundamental processes such as transcription, DNA repair, or DNA replication; because of this, topoisomerases are biological targets in pathogenic microorganisms or malignant cells. In this study, we aimed to identify [...] Read more.

Topoisomerases play a pivotal role in regulating the topological structure of DNA during fundamental processes such as transcription, DNA repair, or DNA replication; because of this, topoisomerases are biological targets in pathogenic microorganisms or malignant cells. In this study, we aimed to identify potential inhibitory compounds against topoisomerases type II of Leishmania mexicana via homology model and molecular docking. A comprehensive screening of 400 compounds provided by Medicines for Malaria Venture (MMV) in the Pandemic Response Box. Here, we identify the 20 best compounds against each topoisomerase type II of L. mexicana to identify new alternatives to treat a neglected tropical disease such as leishmaniasis. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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2716 KiB

Open AccessProceeding Paper

In Silico Investigation of a New 4-Hydroxyquinolone Analogue as an Anaplastic Lymphoma Kinase (ALK) Inhibitor: Molecular Docking and ADMET Prediction

by Yousra Ouafa Bouone, Abdeslem Bouzina and Nour-Eddine Aouf

Chem. Proc. 2023, 14(1), 83; https://doi.org/10.3390/ecsoc-27-16139 - 15 Nov 2023

Viewed by 277

Abstract

In the search for new potential drug candidates acting as anticancer agents, we were interested in a small molecule derived from 4-hydroxy-2-quinolone, which is newly synthesized from the condensation of a β-enaminone and diethylmalonate under microwave irradiation. This compound was subjected to an [...] Read more.

In the search for new potential drug candidates acting as anticancer agents, we were interested in a small molecule derived from 4-hydroxy-2-quinolone, which is newly synthesized from the condensation of a β-enaminone and diethylmalonate under microwave irradiation. This compound was subjected to an in silico study in order to investigate its potentiality to act against lung cancer through inhibiting a tyrosine kinase: Anaplastic Lymphoma Kinase (ALK). A docking simulation was performed in the active pocket of the human ALK complexed with a commercialized anticancer agent—Entrectinib (Pdb: 5FTO)—using Schrodinger suite. The studied derivative showed good stability inside the active site with an estimated docking score equal to −8.054 kcal·mol⁻¹. In addition, significant interactions, similar to those formed by the co-crystallized ligand, were present in the studied compound, counting hydrogen bonds with Met1199 and Glu1197 as well as hydrophobic contacts with residues in the cavity of the ALK. Keeping in mind that the pharmacokinetic properties and the toxicity of a drug candidate are very important factors in conceiving a safe admissible therapeutic substance, we carried out an ADMET prediction for the studied molecules using SwissADME, MolSoft, and ProTox-II, which gave promising results. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1925 KiB

Open AccessProceeding Paper

Comparative Molecular Docking Studies of Selected Phytoconstituents on Adenosine A2A Receptor (PDB ID: 3UZA) as Potential Anti-Parkinson’s Agents

by Namrata Kumari, Priyanka Chandra and Manik Ghosh

Chem. Proc. 2023, 14(1), 84; https://doi.org/10.3390/ecsoc-27-16119 - 15 Nov 2023

Viewed by 381

Abstract

Parkinson’s disease is a neurodegenerative disease which involves the malfunction and death of vital nerve cells in the brain, called neurons, which produce dopamine. Dopamine is a neurotransmitter that communicates with the area of the brain responsible for movement and coordination. As Parkinson’s [...] Read more.

Parkinson’s disease is a neurodegenerative disease which involves the malfunction and death of vital nerve cells in the brain, called neurons, which produce dopamine. Dopamine is a neurotransmitter that communicates with the area of the brain responsible for movement and coordination. As Parkinson’s disease progresses, the amount of dopamine production in the brain declines, leaving a person unable to control movement. Typically, natural compounds such as flavanoids have been cited in the literature for having the ability to penetrate the blood–brain barrier and halt the progression of such disorders. In this study, ten phytoconstituents were screened using molecular docking against adenosine A2A to identify potential inhibitors. Target protein of interest, Adenosine A2A receptor (PDB ID: 3UZA) was extracted from PDB database. Test drugs as well as standard drug were extracted in their 3D conformation from the PubChem in .SDF format, and docking was done using FlexX software. The docking scores of the selected photochemical were compared with levodopa as a positive control. Docking studies revealed that Baicaline has best molecular docking result (−21.6 kcal/mol) for Adenosine A2A receptor, with low toxicity as per pro Tox-II online server which indicates that the Baicalein is a potential lead to be drug candidate for Parkinson’s disease. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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4076 KiB

Open AccessProceeding Paper

Virtual Screening of Natural Compounds as Potential SARS-CoV-2 Main Protease Inhibitors: A Molecular Docking and Molecular Dynamics Simulation Guided Approach

by Deepak K. Lokwani, Sangita R. Chavan, Aniket P. Sarkate, Prabhu M. Natarajan, Vidhya R. Umapathy and Shirish P. Jain

Chem. Proc. 2023, 14(1), 85; https://doi.org/10.3390/ecsoc-27-16049 - 15 Nov 2023

Cited by 2 | Viewed by 295

Abstract

The 2019 coronavirus (COVID-19) pandemic caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has significantly impacted human lives, overburdened the healthcare system, and weakened global economies. The lack of specific drugs against SARS-CoV-2 is a significant hurdle toward the successful treatment of [...] Read more.

The 2019 coronavirus (COVID-19) pandemic caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has significantly impacted human lives, overburdened the healthcare system, and weakened global economies. The lack of specific drugs against SARS-CoV-2 is a significant hurdle toward the successful treatment of COVID-19. The SARS-CoV-2 Main protease (M^pro) is considered an appealing target because of its role in replication in host cells. Plant-derived natural compounds are being largely tested for their efficacy against COVID-19 targets to combat SARS-CoV-2 infection. To discover hit compounds that can be used alone or in combination with repositioned drugs, we curated a set of 224,205 natural product structures from the ZINC database and virtually screened it against COVID-19 M^pro. Sequential docking protocols involving different levels of exhaustiveness were performed to screen a library of natural compounds. The final 88 compounds were selected and post-processed using the MM-GBSA analysis for the generation of binding free energies. The top four compounds (ZINC000085626103, ZINC000085569275, ZINC000085625768, and ZINC000085488571) showed higher affinity against the COVID-19 M^pro enzyme selected for MD simulation studies. The RMSD, RMSF, and RoG analysis of all four compound–protein complexes indicated absolute stability during a 100 ns MD run. Furthermore, the post-MD simulation binding free energies were calculated for all four compounds and were found to be in the range of −38.29 to −18.07 kcal/mol. The in silico virtual screening results suggested that the selected natural compounds have the potential to be developed as a COVID-19 M^pro inhibitor and can be explored further for experimental research to evaluate the in vitro and in vivo efficacy of these compounds for the treatment of COVID-19. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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2511 KiB

Open AccessProceeding Paper

Evaluating a Novel Theoretical Strategy for the Screening DES(s) for Potential Application in EOR Processes Using Quantum Mechanics Calculations

by Maryann I. Uzochukwu, Toyese Oyegoke, Raheem O. Momoh, Muhammed T. Isa, Suleiman M. Shuwa and Baba Y. Jibril

Chem. Proc. 2023, 14(1), 86; https://doi.org/10.3390/ecsoc-27-16040 - 15 Nov 2023

Viewed by 264

Abstract

Green solvents like DES have gained tremendous attention and have been employed for many applications, as industries are now geared toward adopting green materials technologies to contain the effects of climate change, environmental pollution, and global warming. They have found application and use [...] Read more.

Green solvents like DES have gained tremendous attention and have been employed for many applications, as industries are now geared toward adopting green materials technologies to contain the effects of climate change, environmental pollution, and global warming. They have found application and use in enhanced oil recovery in the petroleum industry as surface active materials, among others. However, there is a need to be able to select, screen, and rank the best performance DESs among a large combination of HBA and HBD capable of forming DESs that can perform for enhanced oil recovery (EOR), viz–viz, additional oil recovery. In this study, choline chloride (CHCL)-based DESs, the most employed DES in EOR, are screened for their ability to reduce interfacial tension, adsorption capacities, and oil enhancement. We innovate a screening criterion using molecular descriptors obtained from the interaction of the DES with species (rock, water, oil, and brine) used in the reservoir. Our findings indicate that the correlation of experimental properties with calculated descriptors can be used to predict the overall EOR performance. Our study contributes to valuable insights into the screening of DESs theoretically to be used for EOR. It also can be employed as a quick check to reduce trial and error during the experimental selection of energetically stable DESs in the laboratory for their potential application for EOR performance in a cost-effective manner. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

1442 KiB

Open AccessProceeding Paper

Selective Synthesis of Fatty Alcohols over Mild Reaction Conditions via Non-Catalytic Liquid-Phase Fatty Acid Methyl Esters’ Reduction

by Alejandro Vallejo Orrego, Cristián A. Ferretti and Verónica K. Díez

Chem. Proc. 2023, 14(1), 87; https://doi.org/10.3390/ecsoc-27-16384 - 30 Nov 2023

Viewed by 405

Abstract

The upgrading of fatty alcohols synthesis from natural fatty acid methyl esters’ reduction using alumina-supported NaBH₄ without H₂ supply was investigated. It was possible to synthesize fatty alcohols efficiently with high yields. By using pure NaBH₄ or alumina-supported NaBH₄ [...] Read more.

The upgrading of fatty alcohols synthesis from natural fatty acid methyl esters’ reduction using alumina-supported NaBH₄ without H₂ supply was investigated. It was possible to synthesize fatty alcohols efficiently with high yields. By using pure NaBH₄ or alumina-supported NaBH₄ and methanol as co-reactants, 100% selectivity towards fatty alcohols was achieved. The purpose of supporting the metal hydride is to increase its stability and ensure the recovery of the product at the end of the reaction. A high final fatty alcohol yield was obtained when alumina-supported NaBH₄ was used. The use of more than stoichiometric amounts of methanol and NaBH₄ is important to produce alkoxyborohydride anions that act as better reducing species than NaBH₄. The reaction conditions effect was investigated and the role of short carbon chain alcohol structure was explained. The effect of fatty acid methyl ester structure was also examined. Saturated fatty acid methyl esters (methyl laurate, methyl myristate) with short carbon chains can be easily reduced using NaBH₄/Al₂O₃ and methanol, thus obtaining high conversion and selectable fuel alcohol. Unsaturated fatty acid methyl ester (methyl oleate) with longer carbon shows steric hindrance, which is not suitable for the interaction of esters and reduces the surface area, meaning that the conversion of fatty acid methyl ester is lower. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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3408 KiB

Open AccessProceeding Paper

Green Synthesis of Pistia stratiotes Ag/AgCl Nanomaterials and Their Anti-Bacterial Activity

by Anil Kumar Gautam and Gajanan Pandey

Chem. Proc. 2023, 14(1), 88; https://doi.org/10.3390/ecsoc-27-16054 - 15 Nov 2023

Viewed by 321

Abstract

Over the last few decades, nanomaterials have been synthesized using one-step green approaches, which are rapid, simple, cost-effective, eco-friendly, and nonhazardous. Silver nanomaterials (PS-Ag/AgCl) were synthesized using Pistia stratiotes aqueous leaf extract. The leaf extract acts as a reducing, stabilizing, and capping agent. [...] Read more.

Over the last few decades, nanomaterials have been synthesized using one-step green approaches, which are rapid, simple, cost-effective, eco-friendly, and nonhazardous. Silver nanomaterials (PS-Ag/AgCl) were synthesized using Pistia stratiotes aqueous leaf extract. The leaf extract acts as a reducing, stabilizing, and capping agent. The compounds responsible for the reduction of silver salt and the functional groups present in leaf extract were explored by FT-IR (Fourier-transform infrared spectroscopy) as well as other characterization techniques. The synthesized nanomaterials had a spherical surface morphology and were 15–50 nm in size, according to HR-TEM (high-resolution transmission electron microscopy). UV–visible spectroscopy showed an absorbance peak in the range of 420 nm. Surface morphology was explored by SEM (scanning electron microscopy), and elemental composition was analyzed by EDX (energy-dispersive X-ray spectroscopy). The crystallinity and crystal lattice of Ag/AgCl nanomaterials were explored by XRD (X-ray powder diffraction). The silver nanomaterials showed antibacterial activity against Gram-negative (Escherichia coli) bacteria. As a result, the nanomaterials (PS-Ag/AgCl) are safe and nontoxic. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1040 KiB

Open AccessProceeding Paper

Synthesis of a Bio-Based Methacrylic Polymer Using Camphor Terpene as a Renewable Resource

by Naziha Chabane, Fayçal Dergal, Hervé Pata and Ilyas Chikhi

Chem. Proc. 2023, 14(1), 89; https://doi.org/10.3390/ecsoc-27-16336 - 23 Nov 2023

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Abstract

Sustainable polymers derived from biomass have the potential to reduce environmental impacts while offering significant performance and cost advantages over petrochemical-derived macromolecules. We present here a facile and efficient approach to the synthesis of a biomethacrylic monomer, isobornyl/bornyl methacrylate (IBOMA/BOMA), using the naturally [...] Read more.

Sustainable polymers derived from biomass have the potential to reduce environmental impacts while offering significant performance and cost advantages over petrochemical-derived macromolecules. We present here a facile and efficient approach to the synthesis of a biomethacrylic monomer, isobornyl/bornyl methacrylate (IBOMA/BOMA), using the naturally available camphor terpene in the essential oil of the Algerian plant Artemisia arborescens (Absinthe) as a key intermediate. The essential oil of the aerial part of the Artemisia arborescens plant naturally distributed in northwest Algeria was isolated by hydrodistillation and analyzed using gas chromatography–mass spectrometry (GC/MS) techniques. Nine components were identified, representing 90.7% of the total content. The main constituent of Artemisia arborescens essential oil is camphor (71.8%). Camphor was purified and modified to produce an 80% renewable-carbon-based methacrylic monomer. This terpene-derived methacrylic monomer was free radically polymerized to create a biosourced methacrylic polymer. Nuclear magnetic resonance (NMR) was used to characterize the structure of camphor terpene, isobornyl/bornyl methacrylate, and poly (isobornyl/bornyl methacrylate) (PIBOMA)/(PBOMA). Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1776 KiB

Open AccessProceeding Paper

A Density Functional Theory Study of 4-OH Aldehydes

by Huda Khanam, Ruchi Singh and Jyoti Pandey

Chem. Proc. 2023, 14(1), 90; https://doi.org/10.3390/ecsoc-27-16076 - 15 Nov 2023

Viewed by 186

Abstract

According to certain theories, aldehydes play a significant role as precursor species in the creation of new atmospheric particles. In the current study, we first optimized the structure of the title compound by using the B3LYP 631-G (d, p) basic set. This compound’s [...] Read more.

According to certain theories, aldehydes play a significant role as precursor species in the creation of new atmospheric particles. In the current study, we first optimized the structure of the title compound by using the B3LYP 631-G (d, p) basic set. This compound’s electrostatic potential, electrophilicity (ω), chemical potential (µ), chemical hardness (η), and maximum quantity of electronic charge transfer (Nmax) have all been carefully examined. The hyperconjugated electron interactions within the molecule that contribute to its stability were investigated using natural bond orbital analysis, in order to research the molecule’s chemically active areas. Additionally, reactivity descriptors were determined. The moment of the electric dipole, initial static hyperpolarizability values, and polarizability have been studied for the title compound. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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786 KiB

Open AccessProceeding Paper

Microwave-Assisted BiCl₃ Catalyzed Synthesis of α-Hydroxyphosphonates

by Abdeslem Bouzina, Yousra Ouafa Bouone, Rachida Mansouri and Nour-Eddine Aouf

Chem. Proc. 2023, 14(1), 91; https://doi.org/10.3390/ecsoc-27-16282 - 16 Nov 2023

Viewed by 251

Abstract

In this study, we present a straightforward, resource-efficient, and environmentally sustainable approach for the synthesis of α-hydroxyphosphonate derivatives. This synthetic methodology involves the reaction of aromatic aldehydes with triethylphosphite and utilizes microwave irradiation as a source of activation energy and was catalyzed by [...] Read more.

In this study, we present a straightforward, resource-efficient, and environmentally sustainable approach for the synthesis of α-hydroxyphosphonate derivatives. This synthetic methodology involves the reaction of aromatic aldehydes with triethylphosphite and utilizes microwave irradiation as a source of activation energy and was catalyzed by bismuth chloride III at an amount of 20 mol%. The protocol affords rapid and highly efficient results, yielding α-hydroxyphosphonates in high yields while minimizing reaction times. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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622 KiB

Open AccessProceeding Paper

Optimization, First-Order Hyperpolarizability Studies of o, m, and p-Cl Benzaldehydes Using DFT Studies

by Ruchi Singh, Huda Khanam and Jyoti Pandey

Chem. Proc. 2023, 14(1), 92; https://doi.org/10.3390/ecsoc-27-16072 - 15 Nov 2023

Viewed by 220

Abstract

In this paper, we first optimized the structures of Cl benzaldehydes using Gaussian 09 software with the B3LYP/631-G’ (d,p) basis set. The title compound’s polarizability and hyperpolarizabilities values have been computed, along with an examination of its nonlinear optical characteristics. The title molecule’s [...] Read more.

In this paper, we first optimized the structures of Cl benzaldehydes using Gaussian 09 software with the B3LYP/631-G’ (d,p) basis set. The title compound’s polarizability and hyperpolarizabilities values have been computed, along with an examination of its nonlinear optical characteristics. The title molecule’s total initial static hyperpolarizability as determined by DFT studies may be a topic for future NLO content that is appealing. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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969 KiB

Open AccessProceeding Paper

Ugi-4CR/S_N2-Cyclization Strategy for the One-Pot Synthesis of 2,5-Diketopiperazines

by Diana Garcia-Garcia, Ricardo Ramírez Hernández, Manuel A. Rentería-Gómez and Rocío Gámez-Montaño

Chem. Proc. 2023, 14(1), 93; https://doi.org/10.3390/ecsoc-27-16092 - 15 Nov 2023

Viewed by 199

Abstract

2,5-diketopiperazines (2,5-DKPs) are the smallest cyclic peptides in nature and display a variety of antibacterial, antifungal, and anticancer properties. Very little has been reported on the one-pot synthesis of 2,5-DKPs. Herein, we report a novel one-pot synthesis of 2,5-DKPs via the Ugi-4CR/S_N [...] Read more.

2,5-diketopiperazines (2,5-DKPs) are the smallest cyclic peptides in nature and display a variety of antibacterial, antifungal, and anticancer properties. Very little has been reported on the one-pot synthesis of 2,5-DKPs. Herein, we report a novel one-pot synthesis of 2,5-DKPs via the Ugi-4CR/S_N2-cyclization strategy, under mild conditions, and ethanol was used as a solvent for both procedures. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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7134 KiB

Open AccessProceeding Paper

Computational Model of Adsorption for Hydroxybenzoate Saxitoxin Derivatives (GCs) on Graphene Surface

by Mercedes Álvarez, Manuel Lolo and Álvaro Antelo

Chem. Proc. 2023, 14(1), 94; https://doi.org/10.3390/ecsoc-27-16038 - 15 Nov 2023

Viewed by 206

Abstract

Here, we report on the determination of the supramolecular adsorption of hydroxybenzoate derivates (GC toxins) of saxitoxin to a pristine graphene surface using the computational method, MMFF94 Force Field implemented in the Chem Office package. We use a simple model with the GC [...] Read more.

Here, we report on the determination of the supramolecular adsorption of hydroxybenzoate derivates (GC toxins) of saxitoxin to a pristine graphene surface using the computational method, MMFF94 Force Field implemented in the Chem Office package. We use a simple model with the GC molecule centred on the graphene surface, to simulate the interaction of GC molecule stacking on the graphene system, avoiding edge interactions. We find that the formation of the GC–graphene complex is favourable for all GC molecules. The results of our model are in good agreement with chromatographic elution results on the graphite surface, specifically the Hypercarb column. We predict that these aromatic saxitoxin derivatives possess a higher adsorption energy than non-aromatic ones. π-π stacking can be regarded as being a prevalent contribution compared to non-aromatic analogues. Furthermore, MMFF94 adsorption results yield qualitative agreement with experiments within N-OH and N-H sub-families: in the computational model, the interaction energy value’s order is GC6-GC5-GC4-GC3-GC2-GC1 (the highest adsorption energy). In the experimental Hypercarb model, the elution order is GC3-GC6-GC2-GC5-GC4-GC1 (the highest retention time). The proposed MMFF94 research framework works well in the assessment of chromatographic selectivity. This simple model has the potential for use in predicting the qualitative interactions of small polar molecules and graphene, which sheds light on the application of computational techniques to help in analytical method development. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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903 KiB

Open AccessProceeding Paper

The Biological Properties and Medical Importance of Cassia fistula: A Mini Review

by Ruchi Singh, Huda Khanam and Jyoti Pandey

Chem. Proc. 2023, 14(1), 95; https://doi.org/10.3390/ecsoc-27-16149 - 15 Nov 2023

Viewed by 1044

Abstract

Medicinal plant species contain a variety of chemical substances with high medical potential, making these plant species valuable as biomedical sources. This plant is a deciduous plant also known as “Yellow Shower”. The plant Cassia fistula is considered for its biological importance in [...] Read more.

Medicinal plant species contain a variety of chemical substances with high medical potential, making these plant species valuable as biomedical sources. This plant is a deciduous plant also known as “Yellow Shower”. The plant Cassia fistula is considered for its biological importance in the traditional medication system. This plant is full of different bioactive phytochemicals. In Ayurveda, the plant has also attained medicinal importance. Pharmacological properties like antioxidant, antimicrobial, anti-inflammatory, antidiabetic, antitumor, hepatoprotective, and many more are exhibited by the plant Cassia fistula. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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2555 KiB

Open AccessProceeding Paper

Synthesis and Characterisation of Thymol-Based Hydrophobic Deep Eutectic Solvents

by Deborah Oluwatomilola Adeoye, Zaharaddeen Sani Gano, Omar Umar Ahmed, Suleiman Mohammed Shuwa, Abdulazeez Yusuf Atta and Baba Yakubu Jubril

Chem. Proc. 2023, 14(1), 96; https://doi.org/10.3390/ecsoc-27-16380 - 29 Nov 2023

Viewed by 653

Abstract

The evolution of Hydrophobic Deep Eutectic Solvents (HDESs) has expanded the applications of the new generation of solvents, known as Deep Eutectic Solvents (DES), to include water-based operations. How stable they are in aqueous media qualifies them to be categorised as hydrophobic. This [...] Read more.

The evolution of Hydrophobic Deep Eutectic Solvents (HDESs) has expanded the applications of the new generation of solvents, known as Deep Eutectic Solvents (DES), to include water-based operations. How stable they are in aqueous media qualifies them to be categorised as hydrophobic. This also determines whether they are appropriate materials for water-based industrial processes or not or whether they end up constituting a greater pollution load than those processes due to the leaching of their precursors into the aqueous media when used. This work sought to prepare HDESs from a monoterpene (thymol), and three long-chain organic acids (octanoic acid, decanoic acid, and dodecanoic acid). The physicochemical characteristics of the prepared HDESs were investigated. Thereafter, their moisture absorption capacity and stability in an aqueous environment were determined to ascertain whether they are hydrophobic as predicted. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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901 KiB

Open AccessProceeding Paper

Ultrasound-Assisted Ugi-Azide Multicomponent Reaction for the Synthesis of 1,5-Disubstituted Tetrazoles

by Alejandro Corona-Díaz, Sandra C. Ramírez-López, David Calderón-Rangel, Cristian Saldaña-Arredondo and Rocío Gámez-Montaño

Chem. Proc. 2023, 14(1), 97; https://doi.org/10.3390/ecsoc-27-16078 - 15 Nov 2023

Viewed by 257

Abstract

The Ugi-azide MCR (UA) is one of the most efficient methods for the synthesis of 1,5-disubstituted-1H-tetrazoles (1,5-DS-T). Complex drug-like scaffolds incorporating tetrazoles have demonstrated a wide range of therapeutic benefits such as anti-inflammatory, antiviral, antibiotic, anti-ulcer, anti-anxiety and anti-hypertensive agents, attributable to their [...] Read more.

The Ugi-azide MCR (UA) is one of the most efficient methods for the synthesis of 1,5-disubstituted-1H-tetrazoles (1,5-DS-T). Complex drug-like scaffolds incorporating tetrazoles have demonstrated a wide range of therapeutic benefits such as anti-inflammatory, antiviral, antibiotic, anti-ulcer, anti-anxiety and anti-hypertensive agents, attributable to their mimetic cis amide of peptide bonds that enhance metabolic stability, selectivity and other beneficial physicochemical properties, in addition to their applications in bioimaging, photoimaging and coordination chemistry. Herein, we present the ultrasound-assisted sustainable synthesis of six novel 1,5 DS-T under solvent-free conditions. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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2058 KiB

Open AccessProceeding Paper

Synthesis and Characterisation of Menthol-Based Hydrophobic Deep Eutectic Solvents

by Deborah O. Adeoye, Zaharaddeen S. Gano, Omar U. Ahmed, Suleiman M. Shuwa, Abdulazeez Y. Atta, Samuel A. Iwarere, Baba Y. Jubril and Michael O. Daramola

Chem. Proc. 2023, 14(1), 98; https://doi.org/10.3390/ecsoc-27-16334 - 22 Nov 2023

Viewed by 367

Abstract

Hydrophobic deep eutectic solvents (HDESs) have found applications in water purification in recent years. The extent of their stability in aqueous media determines whether they are suitable materials for water purification or if they end up constituting a greater pollution load to the [...] Read more.

Hydrophobic deep eutectic solvents (HDESs) have found applications in water purification in recent years. The extent of their stability in aqueous media determines whether they are suitable materials for water purification or if they end up constituting a greater pollution load to the water they are to purify. This work sought to prepare HDESs from a monoterpene (menthol), and three long-chain organic acids (octanoic acid, decanoic acid, and dodecanoic acid). The physicochemical characteristics of the prepared HDESs were investigated. Thereafter, their moisture absorption capacity and stability in an aqueous medium were determined to ascertain whether or not they were hydrophobic as predicted. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1962 KiB

Open AccessProceeding Paper

The High Performance of Multi-Metal Layered Double Hydroxides (LDHs) in the Removal of Organic Dyes

by Soumaya Talbi, Amal El Khanchaoui, Latifa Bouissane, Abderrafia Hafid, Mostafa Khouili, Souad Rabi and Abdellatif Essoumhi

Chem. Proc. 2023, 14(1), 99; https://doi.org/10.3390/ecsoc-27-16042 - 15 Nov 2023

Viewed by 253

Abstract

In this work, both MgNiAl-LDH and MgNiFe-LDH hydrotalcites were utilized to remove the anionic dye Congo red (CR) from an aqueous solution. Samples characterization was carried out by X-ray diffraction (XRD), infrared spectroscopy (IR) and Thermogravimetric/Differential Scanning Calorimetry (TG/DSC). Various parameters were investigated, [...] Read more.

In this work, both MgNiAl-LDH and MgNiFe-LDH hydrotalcites were utilized to remove the anionic dye Congo red (CR) from an aqueous solution. Samples characterization was carried out by X-ray diffraction (XRD), infrared spectroscopy (IR) and Thermogravimetric/Differential Scanning Calorimetry (TG/DSC). Various parameters were investigated, including the initial dye concentration, adsorbent mass, contact time, solution pH, and temperature. Using classical pseudo-first-order, pseudo-second-order, and intraparticle diffusion models, adsorption kinetics were investigated. The dynamical data fit well with the pseudo-second order kinetic model. The equilibrium adsorption data were analyzed using three linear adsorption models: Langmuir, Freundlich, and Temkin. The findings showed that the Langmuir isotherm adequately predicts experimental results with an ideal correlation coefficient. The isothermal Langmuir model revealed a maximum adsorption capacity of q_max of 5548 mg/g for the MgNiFe-LDH and of 4043 mg/g for MgNiAl-LDH. This result is very useful when selecting sorbents to improve removal technology in the aquatic environment. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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764 KiB

Open AccessProceeding Paper

In Vitro and In Silico Antioxidant Activity of Hydrazones and Semicarbazones Derived from Aldehydes Found in Essential Oils

by Leandro G. Gutierrez, Carla M. Ormachea, Ana P. Reinick, Vanina A. Guntero and Cristián A. Ferretti

Chem. Proc. 2023, 14(1), 100; https://doi.org/10.3390/ecsoc-27-16577 - 04 Dec 2023

Viewed by 341

Abstract

The aim of this study was to investigate the in vitro and in silico antioxidant properties of four hydrazones and semicarbazones derived from vanillin and cinnamaldehyde, aromatic aldehydes found in essential oils. They were synthesized by condensation of these aldehydes with the corresponding [...] Read more.

The aim of this study was to investigate the in vitro and in silico antioxidant properties of four hydrazones and semicarbazones derived from vanillin and cinnamaldehyde, aromatic aldehydes found in essential oils. They were synthesized by condensation of these aldehydes with the corresponding phenylhydrazine and semicarbazide in good yields. The antioxidant properties of the target molecules were determined using the Reducing Power assay (RP) and the hydrogen peroxide scavenging method (HP), and the results were compared with thermodynamic descriptors obtained from theoretical calculations using the DFT method. The target molecules were shown to be highly active for the total antioxidant assay and the results of theoretical calculations were consistent with the antioxidant activity observed experimentally, making them a useful tool to understand the mechanism of action. This would also allow theoretical tests of new antioxidant compounds to be carried out in a predictive manner. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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7834 KiB

Open AccessProceeding Paper

Comparative Molecular Docking Studies of Selected Phytoconstituents on the Dopamine D3 Receptor (PDB ID: 3PBL) as Potential Anti-Parkinson’s Agents

by Shrimanti Chakraborty, Pallavi Dikshit, Namrata Kumari and Manik Ghosh

Chem. Proc. 2023, 14(1), 101; https://doi.org/10.3390/ecsoc-27-16112 - 15 Nov 2023

Viewed by 378

Abstract

Parkinson’s disease is an idiopathic neurodegenerative disorder which is characterized by the degeneration of the neurons of substantia nigra, a part of the midbrain, regulating motor movement. It involves a decrease in the levels of dopamine which consequently hampers movement control. In the [...] Read more.

Parkinson’s disease is an idiopathic neurodegenerative disorder which is characterized by the degeneration of the neurons of substantia nigra, a part of the midbrain, regulating motor movement. It involves a decrease in the levels of dopamine which consequently hampers movement control. In the literature, natural compounds like flavonoids have been cited to exhibit their potential to terminate the augmentation of such a disorder by penetrating the blood–brain barrier. In this study, 10 phytoconstituents were screened using molecular docking against the dopamine D3 receptor to identify potential inhibitors. The PDB database was employed to extract the target protein of interest, i.e., the dopamine D3 receptor (PDB ID: 3PBL). Both the test drugs and the standard moiety were obtained in their 3D conformation from the PubChem in SDF format, while FlexX software was used for docking purposes. The docking scores of the selected photochemical were hence compared with Levodopa, which was taken as the positive control. The docking studies revealed that Vasicol has the closest docking score (−19.6871 kcal/mol) to that of the standard Levodopa (−23.1188 kcal/mol), proving that it has the best molecular docking result for the dopamine D3 receptor. Also, the low toxicity profile confirmed by the pro Tox-II online server indicated that Vasicol is a potential lead to be a drug candidate for treating Parkinson’s disease. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1295 KiB

Open AccessProceeding Paper

Plant-Derived Triterpenoid Functionalization: Synthesis of α-Acyloxycarboxamides

by Fidel Rodriguez-Lopez, Edgar G. Rodríguez-García, Hugo A. García-Gutiérrez and Rocío Gámez-Montaño

Chem. Proc. 2023, 14(1), 102; https://doi.org/10.3390/ecsoc-27-16061 - 15 Nov 2023

Viewed by 186

Abstract

The application of isocyanide-based multicomponent reactions (IMCRs) for triterpenoid functionalization has been little reported. Triterpenoids and their derivatives are an important class of natural products of interest in medicinal chemistry due to their potential applications as antibacterial, antifungal, and cytotoxic agents. Herein, we [...] Read more.

The application of isocyanide-based multicomponent reactions (IMCRs) for triterpenoid functionalization has been little reported. Triterpenoids and their derivatives are an important class of natural products of interest in medicinal chemistry due to their potential applications as antibacterial, antifungal, and cytotoxic agents. Herein, we describe the use of ethanol as a solvent in the Passerini reaction for the functionalization of masticadienonic acid isolated from fruits and peduncles of P. mexicana. A small series of α-acyloxycarboxamides was synthesized with moderate to good overall yields of 33 to 57%, evaluating and extending the scope of the aldehyde component. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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740 KiB

Open AccessProceeding Paper

One-Pot Synthesis of Imidazo[2,1-b]thiazole via Groebke–Blackburn–Bienaymé Reaction under Free Catalyts

by David Calderón-Rangel, Karla A. González Pérez, Alejandro Corona Díaz and Rocío Gámez-Montaño

Chem. Proc. 2023, 14(1), 103; https://doi.org/10.3390/ecsoc-27-16095 - 15 Nov 2023

Viewed by 199

Abstract

The imidazo[2,1-b]thiazole scaffold is widely present in natural and synthetic compounds with important properties or biological activities, such as anti-inflammatory, anti-bacterial, anti-tuberculosis, cytotoxic, anthelmintic, anti-hypertensive, or herbicidal properties. The isocyanide multicomponent reaction (I-MCR) process is a greener alternative and efficient synthetic [...] Read more.

The imidazo[2,1-b]thiazole scaffold is widely present in natural and synthetic compounds with important properties or biological activities, such as anti-inflammatory, anti-bacterial, anti-tuberculosis, cytotoxic, anthelmintic, anti-hypertensive, or herbicidal properties. The isocyanide multicomponent reaction (I-MCR) process is a greener alternative and efficient synthetic tool. Herein, we describe a novel methodology, one-pot synthesis for the synthesis of imidazo[2,1-b]thiazole by Groebke–Blackburn–Bienaymé reaction (GBBR) using little-explored 3-formylchromone. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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3858 KiB

Open AccessProceeding Paper

Microwave-Irradiation-Assisted Synthesis of Bismuth Ferrite Nanoparticles: Investigating Fuel-to-Oxidant Ratios

by Fatemeh Shahrab and Azadeh Tadjarodi

Chem. Proc. 2023, 14(1), 104; https://doi.org/10.3390/ecsoc-27-16037 - 15 Nov 2023

Viewed by 189

Abstract

Bismuth ferrite, BiFeO₃, a multiferroic perovskite oxide, has gained significant attention in the field of materials science due to its unique combination of ferroelectric and antiferromagnetic properties. This inherent dual nature makes it essential for various cutting-edge technologies, including non-volatile memories, [...] Read more.

Bismuth ferrite, BiFeO₃, a multiferroic perovskite oxide, has gained significant attention in the field of materials science due to its unique combination of ferroelectric and antiferromagnetic properties. This inherent dual nature makes it essential for various cutting-edge technologies, including non-volatile memories, spintronics, and energy-harvesting devices. However, realizing its full potential requires the precise synthesis of high-purity bismuth ferrite nanoparticles. In this scholarly endeavor, we present a comprehensive exploration of the meticulous fabrication of bismuth ferrite nanoparticles using a microwave-assisted combustion method conducted in the solid-state regime. We utilized bismuth nitrate and iron nitrate as precursor materials, combined with an organic fuel amalgam consisting of ammonium nitrate and glycine. Achieving complete combustion through microwave irradiation required a detailed optimization process for the oxidant-to-fuel ratio and absolute quantities. Our research systematically investigated various fuel-to-oxidant ratios, including 1:1, 3:6, 6:3, and 12:12, all conducted under rigorously controlled microwave irradiation conditions. Subsequent characterization through infrared spectroscopy (IR), X-Ray Diffraction (XRD), and scanning electron microscopy (SEM) confirmed the successful synthesis of high-purity bismuth ferrite nanoparticles. Furthermore, optimizing the synthesis conditions resulted in nanoparticles with superior purity and structural integrity. In conclusion, we meticulously evaluated the photocatalytic properties of the synthesized bismuth ferrite nanoparticles, with a specific focus on their effectiveness in degrading malachite green. Our findings highlight the significant impact of carefully tailored combustion parameters on the photocatalytic performance of bismuth ferrite nanoparticles, positioning them as promising candidates for various environmental remediation and catalytic applications. This study advances our understanding of the custom synthesis of advanced photocatalytic materials, potentially fostering sustainable technological advancements. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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2163 KiB

Open AccessProceeding Paper

Suzuki–Miyaura Cross-Coupling for the Synthesis of Key Intermediates of Ketoprofen and Bifonazole Analogues

by Nayane Abreu do Amaral e Silva and Daniela de Luna Martins

Chem. Proc. 2023, 14(1), 105; https://doi.org/10.3390/ecsoc-27-16068 - 15 Nov 2023

Viewed by 199

Abstract

Aromatic ketones are important compounds because of their utility as synthetic intermediates and applications as light absorbing compounds and biological activities. Bifonazole (antifungal) and ketoprofen (anti-inflammatory) are commercial drugs with aryl ketones as synthetic intermediates. The Suzuki coupling reaction is a C-C bond [...] Read more.

Aromatic ketones are important compounds because of their utility as synthetic intermediates and applications as light absorbing compounds and biological activities. Bifonazole (antifungal) and ketoprofen (anti-inflammatory) are commercial drugs with aryl ketones as synthetic intermediates. The Suzuki coupling reaction is a C-C bond forming procedure catalyzed with palladium species under a basic medium. Acyl chlorides can be used as electrophiles in Suzuki couplings, resulting in aryl ketones. In this work, the selectivity in Suzuki coupling reactions between acid chlorides and boronic acids, the catalytic system for such reactions and other aspects of the reaction are studied. The intermediates of interest are 4-bromobenzophenone, 4-phenylbenzophenone and 3-bromobenzophenone. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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4685 KiB

Open AccessProceeding Paper

Biological Docking and BSA Binding Studies of 1,4-Disubstituted Piperdine Containing 1,2,4-Triazoles: Comparative Synthesis Leveraging Microwave-Assisted and Conventional Protocols

by Javed Iqbal, Naeem Akhtar Virk, Aziz Ur Rehman, Aleksey Kuznetsov, Shahid Rasool, Muhammad Yasir and Syed Adnan Ali Shah

Chem. Proc. 2023, 14(1), 106; https://doi.org/10.3390/ecsoc-27-16281 - 15 Nov 2023

Viewed by 876

Abstract

A biologically effective study regarding the synthesis of a library of hybrids based on a triazole ring, propanamide and azinane was performed in this study. The targeted hybrids, 9a–9l, were synthesized through a multistep protocol followed by two methodologies, that is, conventional [...] Read more.

A biologically effective study regarding the synthesis of a library of hybrids based on a triazole ring, propanamide and azinane was performed in this study. The targeted hybrids, 9a–9l, were synthesized through a multistep protocol followed by two methodologies, that is, conventional and microwave-assisted ones. Initially, compound 3 was synthesized via the room-temperature stirring of 4-methoxybenzenesulfonyl chloride (1) and ethyl ester (2). Resulting carboxylate was converted into carbohydrazide 4, which was refluxed with phenyl isothiocyanate and KOH to synthesize product 5. A library of amides, 8a–8l, was stirred at room temperature with compound 5 to avail the targeted library of hybrids 9a–9l. The designed hybrids were screened for their antioxidant, urease, AChE and BChE inhibition potential. All the compounds were found to be active with variable potential. The best antioxidant agent was compound 9c with an IC₅₀ value of 45.2 ± 0.15. The compound 9e (63.27 ± 1.21) was the best AChE inhibitor; 9g (20.2 ± 0.21) and 9k (19.2 ± 0.09) were the best anti-urease agents; and 9d (15.5 ± 0.39) and 9e (15.9 ± 0.67) were the best BChE inhibitors. The computational and BSA binding studies of the selected synthesized compounds against urease, BChE and AChE enzymes were carried out to elaborate the strong and weak enzyme-inhibition potential through the binding forces of the synthesized compounds with the different enzymatic sites that are responsible for their activity. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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2349 KiB

Open AccessProceeding Paper

Organocatalytic Properties of 3,4-Dihydroxyprolines

by Ramón J. Estévez, Rosalino Balo, Andrés Fernández and Juan C. Estévez

Chem. Proc. 2023, 14(1), 107; https://doi.org/10.3390/ecsoc-27-16117 - 15 Nov 2023

Viewed by 165

Abstract

The synthesis and organocatalytic properties of (2S,3R,4R)-3,4-bis((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid are reported. Using the aldol condensation of cyclohexanone with p-nitrobenzaldehyde as a model, a yield of 86%, an enantiomeric excess of 99% and a diastereomeric excess of 25:1 were achieved. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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1432 KiB

Open AccessProceeding Paper

One-Pot Synthesis of Tetrazole–Triazole Bis-Heterocycles via Ugi–Azide Reaction

by Fidel Rodriguez-Lopez, Carlos Zárate-Hernández, Manuel A. Rentería-Gómez and Rocío Gámez-Montaño

Chem. Proc. 2023, 14(1), 108; https://doi.org/10.3390/ecsoc-27-16060 - 15 Nov 2023

Viewed by 136

Abstract

Bioisosteres of amide bonds such as 4,5-disubstituted-1,2,3-triazoles (4,5-DS-1,2,3-Ts) and 1,5-disubstituted tetrazoles (1,5-DST) are present in compounds with important biological activities like those that are antineoplastic, antibacterial, antifungal, and antiparasitic, and antifungal, antiparasitic, antiviral, and anti-inflammatory. In the present work, we describe the synthesis [...] Read more.

Bioisosteres of amide bonds such as 4,5-disubstituted-1,2,3-triazoles (4,5-DS-1,2,3-Ts) and 1,5-disubstituted tetrazoles (1,5-DST) are present in compounds with important biological activities like those that are antineoplastic, antibacterial, antifungal, and antiparasitic, and antifungal, antiparasitic, antiviral, and anti-inflammatory. In the present work, we describe the synthesis of tetrazole–triazole bis-heterocycles via the Ugi–Azide strategy. The target molecules were synthesized with moderate yields, under mild conditions, employing 2H-1,2,3-triazole aldehyde as an input. Full article

(This article belongs to the Proceedings of 27th International Electronic Conference on Synthetic Organic Chemistry)

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