2024

Jump to: 2023, 2022, 2021, 2020, 2019

9 pages, 2545 KiB

Open AccessCommunication

Synthesis and Anti-Inflammatory Activity of (Z)-4-(2-(3-Oxopiperazin-2-ylidene)acetyl)benzoic Acid

by Maksim V. Dmitriev, Ekaterina E. Khramtsova, Danila Y. Apuskin, Alexander I. Andreev, Ilya I. Kovalenko, Irina V. Mashevskaya and Andrey N. Maslivets

Molbank 2024, 2024(1), M1772; https://doi.org/10.3390/M1772 - 05 Feb 2024

Viewed by 949

Abstract

Non-steroidal anti-inflammatory drugs (NSAIDs) are an important class of medications; however, they have some drawbacks. We are developing a new NSAID with pronounced anti-inflammatory and analgesic activities and a very low toxicity—(Z)-3-(2-oxo-2-(p-tolyl)ethylidene)piperazin-2-one (piron). In this work, we describe the synthesis of [...] Read more.

Non-steroidal anti-inflammatory drugs (NSAIDs) are an important class of medications; however, they have some drawbacks. We are developing a new NSAID with pronounced anti-inflammatory and analgesic activities and a very low toxicity—(Z)-3-(2-oxo-2-(p-tolyl)ethylidene)piperazin-2-one (piron). In this work, we describe the synthesis of the main metabolite of piron—(Z)-4-(2-(3-oxopiperazin-2-ylidene)acetyl)benzoic acid. The anti-inflammatory activity of the synthesized metabolite was determined in vivo. Full article

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7 pages, 1581 KiB

Open AccessCommunication

Synthesis of Substituted Pyrrole Derivatives Based on 8-Azaspiro[5.6]dodec-10-ene Scaffold

by Ildar R. Iusupov, Victor A. Tafeenko, Andrea Altieri and Alexander V. Kurkin

Molbank 2024, 2024(1), M1765; https://doi.org/10.3390/M1765 - 25 Jan 2024

Viewed by 1110

Abstract

This work describes the synthesis of spirocyclic compounds based on 8-azaspiro[5.6]dodec-10-ene. Diastereomerically pure pyrrole derivatives were prepared from the spirocyclic 1,2,3-triazole using a coupling reaction. The resulting compounds were characterized via ¹H and ¹³C NMR spectroscopy and HRMS, and the crystallographic [...] Read more.

This work describes the synthesis of spirocyclic compounds based on 8-azaspiro[5.6]dodec-10-ene. Diastereomerically pure pyrrole derivatives were prepared from the spirocyclic 1,2,3-triazole using a coupling reaction. The resulting compounds were characterized via ¹H and ¹³C NMR spectroscopy and HRMS, and the crystallographic characteristics of one of them were studied via X-ray diffraction. Full article

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4 pages, 1252 KiB

Open AccessShort Note

3-(4-Bromophenyl)-1-carbamothioyl-5-(2-carbamothioylhydrazinyl)-4,5-dihydro-1H-pyrazole-5-carboxylic Acid

by Anastasia A. Andreeva, Maksim V. Dmitriev and Andrey N. Maslivets

Molbank 2024, 2024(1), M1757; https://doi.org/10.3390/M1757 - 02 Jan 2024

Viewed by 1315

Abstract

The reaction of 4-(4-bromophenyl)-2,4-dioxobutanoic acid with thiosemicarbazide, in a ratio of 1:2, when boiled in ethanol gives 3-(4-bromophenyl)-1-carbamothioyl-5-(2-carbamothioylhydrazinyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid with a good yield. This compound was fully characterized. Full article

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2023

Jump to: 2024, 2022, 2021, 2020, 2019

4 pages, 1379 KiB

Open AccessShort Note

(Z)-1-Benzyl-5-(4-bromophenyl)-5-hydroxy-4-(2-oxomorpholin-3-ylidene)pyrrolidine-2,3-dione

by Nikita A. Tretyakov and Andrey N. Maslivets

Molbank 2023, 2023(4), M1751; https://doi.org/10.3390/M1751 - 18 Dec 2023

Viewed by 1247

Abstract

The reaction of 8-(4-bromobenzoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,6,7-trione with benzylamine in acetonitrile at room temperature afforded a good yield of (Z)-1-benzyl-5-(4-bromophenyl)-5-hydroxy-4-(2-oxomorpholin-3-ylidene)pyrrolidine-2,3-dione. The compound was fully characterized. Full article

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7 pages, 4926 KiB

Open AccessShort Note

3-Benzoyl-2-hydroxy-3a-[(3-methylquinoxalin-2-yl)methyl]-1H-pyrrolo[2,1-c][1,4]benzothiazine-1,4(3aH)-dione

by Ekaterina A. Lystsova and Ekaterina E. Khramtsova

Molbank 2023, 2023(4), M1749; https://doi.org/10.3390/M1749 - 13 Dec 2023

Viewed by 1136

Abstract

The reaction of 3-benzoylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-trione with 2,3-dimethylquinoxaline afforded 3-benzoyl-2-hydroxy-3a-[(3-methylquinoxalin-2-yl)methyl]-1H-pyrrolo[2,1-c][1,4]benzothiazine-1,4(3aH)-dione in a moderate yield. The compound was fully characterized. Full article

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9 pages, 1159 KiB

Open AccessCommunication

Potassium 6-Oxo-7,13,16,22-tetraazatetracyclo[12.6.2.1^8,12.0^17,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate

by Camille Blouet, Stéphanie Letast, Thomas Robert, Stéphane Bach, Noël Pinaud, Nicolas Joubert, Marie-Claude Viaud-Massuard, Jean Guillon, Cédric Logé and Caroline Denevault-Sabourin

Molbank 2023, 2023(4), M1735; https://doi.org/10.3390/M1735 - 09 Oct 2023

Viewed by 1110

Abstract

Potassium 6-oxo-7,13,16,22-tetraazatetracyclo[12.6.2.1^8,12.0^17,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate was synthesized through a multi-step pathway, starting from commercially available 3-iodo-1,2-phenylenediamine. Structure characterization of this new substituted macrocyclic quinoxaline compound was achieved using ¹H NMR, ¹³C NMR, and HRMS spectral analysis. This new macrocyclic derivative [...] Read more.

Potassium 6-oxo-7,13,16,22-tetraazatetracyclo[12.6.2.1^8,12.0^17,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate was synthesized through a multi-step pathway, starting from commercially available 3-iodo-1,2-phenylenediamine. Structure characterization of this new substituted macrocyclic quinoxaline compound was achieved using ¹H NMR, ¹³C NMR, and HRMS spectral analysis. This new macrocyclic derivative demonstrated submicromolar potency on both Pim-1 and Pim-2 isoforms, with an interesting selectivity profile against a selected panel of human kinases. Full article

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Graphical abstract

4 pages, 827 KiB

Open AccessShort Note

4-(4-(2-Bromoethyl)phenoxy)-2,3,5,6-tetrafluoropyridine

by Tiffany H. Li, Lucas C. Messer, Nathan J. Weeks, Timothy J. Fuhrer and Scott T. Iacono

Molbank 2023, 2023(3), M1730; https://doi.org/10.3390/M1730 - 19 Sep 2023

Cited by 1 | Viewed by 1089

Abstract

The title compound was synthesized in near quantitative yields via initial nucleophilic aromatic substitution of pentafluoropyridine (PFP) with 4-(2-bromoethyl)phenol as a versatile precursor for ionic liquids (ILs). The purity and structure were determined using ¹H, ¹³C, and ¹⁹F NMR and GC-EIMS. Full article

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Scheme 1

4 pages, 612 KiB

Open AccessShort Note

4-(2,5-Dimethyl-1H-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine

by Natalia V. Obruchnikova and Oleg A. Rakitin

Molbank 2023, 2023(3), M1700; https://doi.org/10.3390/M1700 - 20 Jul 2023

Viewed by 718

Abstract

1,2,5-Oxadiazol-3-amines with a heterocyclic substituent in the 4-position are being intensively investigated as compounds with valuable pharmacological activity. In this communication, the reaction of 1,2,5-oxadiazole-3,4-diamine with 2,5-hexanedione was shown to selectively give 4-(2,5-dimethyl-1H-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine as a product of the Paal–Knorr reaction. The [...] Read more.

1,2,5-Oxadiazol-3-amines with a heterocyclic substituent in the 4-position are being intensively investigated as compounds with valuable pharmacological activity. In this communication, the reaction of 1,2,5-oxadiazole-3,4-diamine with 2,5-hexanedione was shown to selectively give 4-(2,5-dimethyl-1H-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine as a product of the Paal–Knorr reaction. The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, ¹H and ¹³C NMR, and IR spectroscopy. Full article

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Scheme 1

5 pages, 606 KiB

Open AccessShort Note

3-(4-(Benzyloxy)-3-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine

by Katrina E. Doherty, Arturo León Sandoval, Ethan T. Mercier and Nicholas E. Leadbeater

Molbank 2023, 2023(3), M1694; https://doi.org/10.3390/M1694 - 12 Jul 2023

Viewed by 834

Abstract

The [1,2,4]triazolo[4,3-a]pyridine derivative 3-(4-(benzyloxy)-3-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine was prepared in a 73% isolated yield by means of an oxidative ring closure of a hydrazine intermediate. Sodium hypochlorite was used as the oxidant and ethanol as a solvent, making the process a clean, [...] Read more.

The [1,2,4]triazolo[4,3-a]pyridine derivative 3-(4-(benzyloxy)-3-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine was prepared in a 73% isolated yield by means of an oxidative ring closure of a hydrazine intermediate. Sodium hypochlorite was used as the oxidant and ethanol as a solvent, making the process a clean, green approach. The reaction was performed at room temperature for 3 h, and then the heterocycle was isolated in an analytically pure form by extraction, followed by passing the crude product mixture through a small plug of alumina. Full article

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Graphical abstract

8 pages, 908 KiB

Open AccessShort Note

2-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

by Perla Islas-Jácome, Cecilia García-Falcón, Sandra L. Castañón-Alonso, Ernesto Calderón-Jaimes, Daniel Canseco-González, Alejandro Islas-Jácome and Eduardo González-Zamora

Molbank 2023, 2023(3), M1693; https://doi.org/10.3390/M1693 - 10 Jul 2023

Viewed by 900

Abstract

The new polyheterocyclic compound, 2-benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, was synthesized by a sequential combination of 4-chlorobenzaldehyde, (1-phenyl-1H-1,2,3-triazol-4-yl)methanamine, 2-isocyano-1-morpholino-3-phenylpropan-1-one, and maleic anhydride under a microwave-assisted one-pot process [Ugi-Zhu/aza Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration] with a 28% overall yield. The synthesized [...] Read more.

The new polyheterocyclic compound, 2-benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, was synthesized by a sequential combination of 4-chlorobenzaldehyde, (1-phenyl-1H-1,2,3-triazol-4-yl)methanamine, 2-isocyano-1-morpholino-3-phenylpropan-1-one, and maleic anhydride under a microwave-assisted one-pot process [Ugi-Zhu/aza Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration] with a 28% overall yield. The synthesized compound was fully characterized by 1D (¹H, ¹³C) and 2D (COSY, HSQC, and HMBC) NMR, FT-IR, and HRMS. Full article

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Graphical abstract

7 pages, 912 KiB

Open AccessCommunication

Synthesis, Characterization and Chlorination of 4-(Pentyloxy)-7-(prop-2-yn-1-yloxy)pteridin-2-amine

by Jevy V. Correia, Bruno Wilke and Carola Schulzke

Molbank 2023, 2023(3), M1692; https://doi.org/10.3390/M1692 - 08 Jul 2023

Viewed by 1101

Abstract

A new alkyne functionalized pterin derivative was synthesized through a reaction of 7-chloropterin with propargyl alcohol in the presence of sodium hydride. The purity and chemical structure of the compound was validated by NMR (¹H, ¹³C) spectroscopy, Mass (APCI source) [...] Read more.

A new alkyne functionalized pterin derivative was synthesized through a reaction of 7-chloropterin with propargyl alcohol in the presence of sodium hydride. The purity and chemical structure of the compound was validated by NMR (¹H, ¹³C) spectroscopy, Mass (APCI source) spectrometry, elemental analysis, and X-ray crystallography. The title compound may be further functionalized by exploiting the yne moiety, for instance, using click chemistry. The novel pterin derivative, most notably, in contrast to typical pterin behavior, is now soluble or even well soluble in almost any solvent except water. Full article

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7 pages, 1985 KiB

Open AccessCommunication

Synthesis, Spectroscopic, and Thermal Analyses of 2-Oxo-1,2-dihydroquinolin-8-yl 4-chlorobenzoate

by Diana Becerra, Hugo Rojas and Juan-Carlos Castillo

Molbank 2023, 2023(2), M1672; https://doi.org/10.3390/M1672 - 19 Jun 2023

Viewed by 831

Abstract

The 2-oxo-1,2-dihydroquinolin-8-yl 4-chlorobenzoate was synthesized in good yield using a triethylamine-mediated O-acylation reaction between 8-hydroxyquinolin-2(1H)-one and 4-chlorobenzoyl chloride in acetonitrile at room temperature. This methodology is notable for its clean reaction profile and straightforward procedure. The 2-oxoquinoline derivative was characterized [...] Read more.

The 2-oxo-1,2-dihydroquinolin-8-yl 4-chlorobenzoate was synthesized in good yield using a triethylamine-mediated O-acylation reaction between 8-hydroxyquinolin-2(1H)-one and 4-chlorobenzoyl chloride in acetonitrile at room temperature. This methodology is notable for its clean reaction profile and straightforward procedure. The 2-oxoquinoline derivative was characterized using spectroscopic, spectrometric, and thermal analyses, enabling a comprehensive understanding of its molecular structure and thermal properties. Full article

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7 pages, 2204 KiB

Open AccessCommunication

Photoinduced Ring Opening of Methyl 1-Aryl-5-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylates in the Presence of Diaryl Disulfides

by Nejc Petek and Uroš Grošelj

Molbank 2023, 2023(2), M1670; https://doi.org/10.3390/M1670 - 15 Jun 2023

Viewed by 814

Abstract

Among the methods used for the synthesis of functionalized heterocyclic compounds, photochemistry has gained immense popularity due to the reactivity of intermediates in photoinduced reactions. In this study, we report on the effect of diaryl disulfides as hydrogen atom transfer catalysts on the [...] Read more.

Among the methods used for the synthesis of functionalized heterocyclic compounds, photochemistry has gained immense popularity due to the reactivity of intermediates in photoinduced reactions. In this study, we report on the effect of diaryl disulfides as hydrogen atom transfer catalysts on the photoinduced transformations of pyrazolo[1,2-a]pyrazolones. After excitation with visible light, these compounds are susceptible to C–N bond cleavage, followed by intermolecular hydrogen atom abstraction. By modifying the reaction conditions, we have developed two novel methods for the synthesis of highly substituted pyrazoles. Full article

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Scheme 1

5 pages, 600 KiB

Open AccessCommunication

Synthesis of 5-Aroyl-2-aryl-3-hydroxypyridin-4(1H)-ones

by Elena V. Steparuk, Dmitrii L. Obydennov and Vyacheslav Y. Sosnovskikh

Molbank 2023, 2023(2), M1668; https://doi.org/10.3390/M1668 - 10 Jun 2023

Cited by 1 | Viewed by 1095

Abstract

A two-stage synthesis of 5-aroyl-2-aryl-3-hydroxypyridin-4(1H)-ones (56–66% overall yields) was carried out by refluxing 5-aroyl-3-(benzyloxy)-2-(het)aryl-4H-pyran-4-ones with ammonium acetate in AcOH and subsequent debenzylation. The prepared N-unsubstituted 4-pyridones exist in the pyridone tautomeric form. Full article

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Graphical abstract

4 pages, 321 KiB

Open AccessShort Note

5,6-Dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione

by Timofey N. Chmovzh, Karim S. Gaisin and Oleg A. Rakitin

Molbank 2023, 2023(2), M1649; https://doi.org/10.3390/M1649 - 18 May 2023

Viewed by 1103

Abstract

1,2,5-Chalcogenadiazoles fused with electron-withdrawing heterocycles have been actively investigated for the preparation of organic photovoltaic materials. [1,2,5]Oxadiazolo[3,4-d]pyridazines are much less studied than other chalcogenadiazolopyridazines due to their low availability. In this communication, we report our study showing that 5,6-dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione, a key precursor for [...] Read more.

1,2,5-Chalcogenadiazoles fused with electron-withdrawing heterocycles have been actively investigated for the preparation of organic photovoltaic materials. [1,2,5]Oxadiazolo[3,4-d]pyridazines are much less studied than other chalcogenadiazolopyridazines due to their low availability. In this communication, we report our study showing that 5,6-dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione, a key precursor for the synthesis of 4,7-dihalo-[1,2,5]oxadiazolo[3,4-d]pyridazines, is formed via the cyclization of 1,2,5-oxadiazole-3,4-dicarbohydrazide in hydrochloric acid. The structure of the newly synthesized compound was established by means of elemental analysis; high-resolution mass spectrometry; ¹H and ¹³C NMR; IR spectroscopy, and mass spectrometry. Full article

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Graphical abstract

6 pages, 1690 KiB

Open AccessShort Note

5-(4-Chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine

by Francesco Messa, Paride Papadia, Serena Perrone and Antonio Salomone

Molbank 2023, 2023(2), M1648; https://doi.org/10.3390/M1648 - 17 May 2023

Viewed by 1095

Abstract

A new 2-amino imidazole derivative, 5-(4-chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine (3), has been synthesized using a green approach. The reaction was conducted in a ChCl (cholinium chloride)/urea eutectic mixture, which is a nature-inspired and environmentally friendly reaction medium. The proposed reaction mechanism involves [...] Read more.

A new 2-amino imidazole derivative, 5-(4-chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine (3), has been synthesized using a green approach. The reaction was conducted in a ChCl (cholinium chloride)/urea eutectic mixture, which is a nature-inspired and environmentally friendly reaction medium. The proposed reaction mechanism involves the preliminary regioselective alkylation of the N_sp2 of guanidine (2), followed by an intramolecular condensation between the carbonyl moiety and the secondary N′_sp3. Finally, a tautomerization/aromatization step furnished the final product (3). Notably, 2-amino imidazole (3) could be isolated in high yield (91%), just by filtration from the DES/water mixture and subsequent crystallization; the remaining ChCl/urea could be recycled, after water removal, for four consecutive reactions without any significant drop in the (3) yield. The product has been fully characterized by ¹H, ¹³C, 2D ¹H-¹³C HSQC, and 2D ¹H-¹³C HMBC NMR; FT-IR spectroscopy; and EI-MS spectrometry. Full article

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Figure 1

5 pages, 517 KiB

Open AccessShort Note

5-(1-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione

by Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Fedor V. Ryzhkov and Michail N. Elinson

Molbank 2023, 2023(2), M1640; https://doi.org/10.3390/M1640 - 08 May 2023

Viewed by 1286

Abstract

Multicomponent reactions have been demonstrated as a promising tool for the creation of diverse molecular structures with enhanced efficiency, reduced waste, and a high atom economy. Arylglyoxal monohydrates with two different carbonyl groups are well known as worthwhile synthons in organic synthesis. 2-Pyrone [...] Read more.

Multicomponent reactions have been demonstrated as a promising tool for the creation of diverse molecular structures with enhanced efficiency, reduced waste, and a high atom economy. Arylglyoxal monohydrates with two different carbonyl groups are well known as worthwhile synthons in organic synthesis. 2-Pyrone and pyrimidine-2,4,6-trione are versatile building blocks for the synthesis of key intermediates in synthetic organic chemistry as well as in medicinal chemistry. A simple and efficient tandem Knoevenagel–Michael protocol for the synthesis of the previously unknown 5-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimet-hylpyrimidine-2,4,6(1H,3H,5H)-trione was elaborated. The suggested method is based on the multicomponent reaction of phenylglyoxal hydrate, 1,3-dimethylbarbituric acid, and 4-hydroxy-6-methyl-2H-pyran-2-one. The structure of the synthesized compound was proven by ¹H, ¹³C-NMR, and IR spectroscopy, mass spectrometry, and elemental analysis. A procedure for predicting the possible types of its biological activity was carried out for the title compound. Full article

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Scheme 1

5 pages, 1560 KiB

Open AccessShort Note

N-[1-(2-Chlorophenyl)-2-{1-methyl-5-nitro-4-[(phenylsulfonyl)methyl]-1H-imidazol-2-yl}ethyl]-4-methylbenzenesulfonamide

by Romain Paoli-Lombardo, Nicolas Primas, Caroline Castera-Ducros, Inès Jacquet, Pascal Rathelot and Patrice Vanelle

Molbank 2023, 2023(2), M1633; https://doi.org/10.3390/M1633 - 25 Apr 2023

Viewed by 1009

Abstract

In continuation of our research program to develop original synthetic methods using TDAE methodology on nitroheterocyclic substrates, we were able to generate for the first time a stable carbanion in position 2 of the 5-nitroimidazole scaffold. Starting from a 2-chloromethyl-4-phenylsulfonylmethyl-5-nitroimidazole intermediate, prepared by [...] Read more.

In continuation of our research program to develop original synthetic methods using TDAE methodology on nitroheterocyclic substrates, we were able to generate for the first time a stable carbanion in position 2 of the 5-nitroimidazole scaffold. Starting from a 2-chloromethyl-4-phenylsulfonylmethyl-5-nitroimidazole intermediate, prepared by the vicarious nucleophilic substitution of hydrogen (VNS) reaction, we selectively introduced a N-tosylbenzylimine moiety at position 2 without reducing the sulfone at position 4, leading to the formation of N-[1-(2-chlorophenyl)-2-{1-methyl-5-nitro-4-[(phenylsulfonyl)methyl]-1H-imidazol-2-yl}ethyl]-4-methylbenzenesulfonamide in 47% yield. This new synthetic method using TDAE should allow access to new 2-substituted 5-nitroimidazole derivatives with various electrophiles such as carbonyls and other N-tosylbenzylimines. Full article

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Figure 1

4 pages, 783 KiB

Open AccessShort Note

9-Methoxynaphtho[1,2-b]benzofuran

by Roberto Miani, Jacopo Vigna and Ines Mancini

Molbank 2023, 2023(2), M1632; https://doi.org/10.3390/M1632 - 25 Apr 2023

Cited by 1 | Viewed by 978

Abstract

A highly selective one-pot microwave-assisted synthesis of 9-methoxynaphtho[1,2-b]benzofuran was obtained by treating 1-naphthol with 1-bromo-4-methoxy-2-nitrobenzene and two molar equivalents of potassium tert-butoxide in dimethyl sulfoxide. The selectivity in the production of the title compound was addressed by the suitable position [...] Read more.

A highly selective one-pot microwave-assisted synthesis of 9-methoxynaphtho[1,2-b]benzofuran was obtained by treating 1-naphthol with 1-bromo-4-methoxy-2-nitrobenzene and two molar equivalents of potassium tert-butoxide in dimethyl sulfoxide. The selectivity in the production of the title compound was addressed by the suitable position of the bromine and nitro group on the aryl reagent. Moreover, we highlight how the nitro group plays a dual role, as activator in the first nucleophilic substitution with the release of bromide ion and then as the leaving group in the furan cyclization. Eventually, the product was structurally characterized by MS and extensive NMR analyses. Full article

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Scheme 1

5 pages, 1135 KiB

Open AccessShort Note

2-(2,5-Dimethoxyphenyl)pyrrole-3-carbonitrile

by Yannic Grimm, Dieter Schollmeyer and Heiner Detert

Molbank 2023, 2023(2), M1627; https://doi.org/10.3390/M1627 - 20 Apr 2023

Viewed by 1204

Abstract

The Cadogan reaction of 2-aryl-3-nitropyridines leads to δ-carbolines. The title compound is a side product in this reaction, generated via a ring opening of a nitrene and cyclization. A crystal structure analysis gives an enormous unit cell. Full article

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Figure 1

8 pages, 3193 KiB

Open AccessCommunication

3a-(4-Chlorophenyl)-1-methyl-3a,4-dihydroimidazo[1,5-a]quinazolin-5(3H)-one: Synthesis and In Silico Evaluation as a Ligand in the µ-Opioid Receptor

by Andrea Defant, Nicole Innocenti and Ines Mancini

Molbank 2023, 2023(2), M1622; https://doi.org/10.3390/M1622 - 17 Apr 2023

Cited by 1 | Viewed by 1154

Abstract

In the search for fused heterocycle molecules with potential biological activities, the new title compound was produced in racemic form via a four step-synthetic sequence with an overall yield of 60%. It was structurally characterised via ¹H-, ¹³C-NMR and IR analyses, [...] Read more.

In the search for fused heterocycle molecules with potential biological activities, the new title compound was produced in racemic form via a four step-synthetic sequence with an overall yield of 60%. It was structurally characterised via ¹H-, ¹³C-NMR and IR analyses, and the molecular composition was confirmed through a high-resolution MS experiment. After predicting its analgesic activity using PASS online software, wherein a good overlap between its enantiomers and the structure of the natural opioid morphine was observed, the compound was evaluated through docking calculations as a ligand of the µ-opioid receptor. The resulting energy values and interactions were comparable to the data obtained for morphine and its synthetic derivative fentanyl, which is used in the therapeutic treatment of severe forms of pain. Moreover, the title compound displayed favourable predicted blood–brain barrier permeation and drug-likeness. Full article

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Figure 1

4 pages, 796 KiB

Open AccessShort Note

2-(3-Bromophenyl)imidazo[2,1-b]oxazole

by Ángel Cores, Mercedes Villacampa and J. Carlos Menéndez

Molbank 2023, 2023(2), M1616; https://doi.org/10.3390/M1616 - 04 Apr 2023

Viewed by 1183

Abstract

The microwave-assisted reaction of 2-nitroimidazole with 3-bromophenacyl bromide in the presence of potassium carbonate as a base and dimethylformamide as a solvent afforded 2-(3-bromophenyl)imidazo[2,1-b]oxazole. The formation of this compound was explained via a domino mechanism comprising an initial N-alkylation reaction of [...] Read more.

The microwave-assisted reaction of 2-nitroimidazole with 3-bromophenacyl bromide in the presence of potassium carbonate as a base and dimethylformamide as a solvent afforded 2-(3-bromophenyl)imidazo[2,1-b]oxazole. The formation of this compound was explained via a domino mechanism comprising an initial N-alkylation reaction of the imidazole substrate, followed by the base-promoted deprotonation of the position adjacent to the carbonyl to give an enolate anion that finally cyclizes via an intramolecular S_NAr reaction, with the loss of the nitro group as potassium nitrite. Then, the proposed 1-(3-bromophenacyl)-2-nitroimidazole intermediate could be isolated by reducing the reaction time and was shown to be a precursor of the imidazo[2,1-b]oxazole final product. Full article

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Scheme 1

5 pages, 960 KiB

Open AccessShort Note

tert-Butyl (E)-3-oxo-2-(3-oxoisobenzofuran-1(3H)-ylidene)butanoate

by Alexandra S. Chechulina, Ekaterina A. Knyazeva, Bin Kan, Tainan Duan and Oleg A. Rakitin

Molbank 2023, 2023(2), M1614; https://doi.org/10.3390/M1614 - 30 Mar 2023

Viewed by 1248

Abstract

Non-fullerene acceptors have recently attracted much attention as components of organic solar cells. 1H-indene-1,3(2H)-dione is a key compound for the synthesis of the end-capping component of non-fullerene acceptors. In this communication, an intermediate for the synthesis of this compound, [...] Read more.

Non-fullerene acceptors have recently attracted much attention as components of organic solar cells. 1H-indene-1,3(2H)-dione is a key compound for the synthesis of the end-capping component of non-fullerene acceptors. In this communication, an intermediate for the synthesis of this compound, tert-butyl (E)-3-oxo-2-(3-oxoisobenzofuran-1(3H)-ylidene)butanoate, was prepared by the reaction between phthalic anhydride and tert-butyl acetoacetate. Further treatment with sodium methoxide in methanol led to the formation of 1H-indene-1,3(2H)-dione in a high yield. The structure of the newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, ¹H, ¹³C NMR, IR spectroscopy, mass spectrometry and X-ray analysis. Full article

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Graphical abstract

6 pages, 706 KiB

Open AccessShort Note

New 2-(2,4-Dihydroxyphenyl)benzimidazolines

by Yordan Stremski, Maria Bachvarova, Desislava Kirkova and Stela Statkova-Abeghe

Molbank 2023, 2023(1), M1602; https://doi.org/10.3390/M1602 - 10 Mar 2023

Viewed by 1116

Abstract

New 2-(2,4-dihydroxyphenyl)benzimidazolines are synthesized in an easily accessible approach. The method is based on the reaction of resorcinol with in situ-formed electrophilic N-ethoxycarbonylbenzimidazolium reagents. The structure of the two newly formed products was spectrally characterized by 1D and 2D NMR, IR, and [...] Read more.

New 2-(2,4-dihydroxyphenyl)benzimidazolines are synthesized in an easily accessible approach. The method is based on the reaction of resorcinol with in situ-formed electrophilic N-ethoxycarbonylbenzimidazolium reagents. The structure of the two newly formed products was spectrally characterized by 1D and 2D NMR, IR, and MS spectral analyses. Full article

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Graphical abstract

3 pages, 321 KiB

Open AccessShort Note

4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide

by Natalia V. Obruchnikova and Oleg A. Rakitin

Molbank 2023, 2023(1), M1596; https://doi.org/10.3390/M1596 - 23 Feb 2023

Viewed by 1037

Abstract

1,2,5-Oxadiazole oxides (furoxans) are well known nitric oxide donors; among them, 4-fluorofuroxans have recently been found to be important photoinduced nitric oxide donors. In this research, it was shown that the reaction of 4,4′-dinitro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide with fluoro-containing reagents (tetrabutylammonium fluoride or cesium fluoride) [...] Read more.

1,2,5-Oxadiazole oxides (furoxans) are well known nitric oxide donors; among them, 4-fluorofuroxans have recently been found to be important photoinduced nitric oxide donors. In this research, it was shown that the reaction of 4,4′-dinitro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide with fluoro-containing reagents (tetrabutylammonium fluoride or cesium fluoride) selectively gave the bis-substitution product 4,4′-difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide. The structure of the synthesized compound was established by elemental analysis, ¹³C, ¹⁹F-NMR and IR spectroscopy, and mass-spectrometry. Full article

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Scheme 1

7 pages, 2512 KiB

Open AccessShort Note

(E)-1-(5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one Oxime

by Bakr F. Abdel-Wahab, Abdelbasset A. Farahat, Benson M. Kariuki and Gamal A. El-Hiti

Molbank 2023, 2023(1), M1593; https://doi.org/10.3390/M1593 - 21 Feb 2023

Cited by 3 | Viewed by 1308

Abstract

The reaction of 1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (1) with excess hydroxylamine hydrochloride (2 mole equivalents) in dry ethanol afforded (E)-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one oxime (2) in 86% yield. The structure of the new heterocycle 2 was confirmed using nuclear magnetic resonance spectroscopy, single crystal X-ray and elemental analysis. Full article

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Graphical abstract

7 pages, 1807 KiB

Open AccessShort Note

Triethylammonium 2-(3-Hydroxy-2-oxoindolin-3-yl)-5,5-dimethyl-3-oxocyclohex-1-en-1-olate

by Yuliya E. Ryzhkova, Fedor V. Ryzhkov and Michail N. Elinson

Molbank 2023, 2023(1), M1589; https://doi.org/10.3390/M1589 - 15 Feb 2023

Cited by 1 | Viewed by 1231

Abstract

In recent years, the application of privileged structures has become a powerful approach in the discovery of new biologically active molecules. Ion pairing is a strategy used to enhance the permeation of ionized topical drugs. A convenient and efficient method for the synthesis [...] Read more.

In recent years, the application of privileged structures has become a powerful approach in the discovery of new biologically active molecules. Ion pairing is a strategy used to enhance the permeation of ionized topical drugs. A convenient and efficient method for the synthesis of triethylammonium 2-(3-hydroxy-2-oxoindolin-3-yl)-5,5-dimethyl-3-oxocyclohex-1-en-1-olate has been developed. The presented protocol includes an aldol reaction and the formation of an ammonium salt. Triethylamine is both a reactant and a catalyst in the process. The structure of the synthesized title compound has been established by ¹H, ¹³C-NMR and IR spectroscopy, mass spectrometry, and elemental analysis. Full article

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Graphical abstract

4 pages, 1133 KiB

Open AccessShort Note

4-Benzoyl-2-(4-bromophenyl)-1-(4-methoxyphenyl)-1,2-dihydropyrimidino[4,3-c][1,4]benzoxazine-3,5-dione

by Ekaterina E. Khramtsova, Maksim V. Dmitriev and Andrey N. Maslivets

Molbank 2023, 2023(1), M1583; https://doi.org/10.3390/M1583 - 08 Feb 2023

Viewed by 1118

Abstract

The reaction of 3-benzoylpyrrolo[2,1-c][1,4]benzoxazin-1,2,4-trione with N-(4-bromophenyl)-1-(4-methoxyphenyl)methanimine under thermolytical conditions afforded 4-benzoyl-2-(4-bromophenyl)-1-(4-methoxyphenyl)-1,2-dihydropyrimidino[4,3-c][1,4]benzoxazine-3,5-dione in a good yield. The reaction proceeded via in situ generation of a reactive intermediate, acyl(imidoyl)ketene. The compound was fully characterized. Full article

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Figure 1

10 pages, 2059 KiB

Open AccessShort Note

(Z)-3-(Dicyanomethylene)-4-((5-fluoro-3,3-dimethyl-1-(3-phenylpropyl)-3H-indol-1-ium-2-yl) methylene)-2-(((E)-5-fluoro-3,3-dimethyl-1-(3-phenylpropyl)indolin-2-ylidene)methyl) cyclobut-1-en-1-olate

by Stefanie Casa, Guliz Ersoy Ozmen and Maged Henary

Molbank 2023, 2023(1), M1576; https://doi.org/10.3390/M1576 - 03 Feb 2023

Cited by 1 | Viewed by 1335

Abstract

Recent literature on this topic highlights the significance of adding malononitrile moiety and halogen substituents to the squaraine scaffold to create redshifted fluorophores into the near-infrared optical region. Herein, a redshifted hydrophobic squaraine dye is synthesized via a three-step pathway. The reported dye [...] Read more.

Recent literature on this topic highlights the significance of adding malononitrile moiety and halogen substituents to the squaraine scaffold to create redshifted fluorophores into the near-infrared optical region. Herein, a redshifted hydrophobic squaraine dye is synthesized via a three-step pathway. The reported dye is characterized by spectroscopic techniques, such as ¹H NMR, ¹⁹F NMR, ¹³C NMR, and high-resolution mass spectroscopy. Optical properties are also reported using absorbance and fluorescence studies. The hydrophobicity of the dye was studied with absorbance and fluorescence spectroscopy in water–methanol mixtures and showed J-aggregates as the water concentration increased. Density functional theory calculations were conducted to assess its electron delocalization as well as observe the three-dimensional geometry of the dye as a result of the dicyanomethylene modification and the two bulky phenyl groups. Full article

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Graphical abstract

7 pages, 1071 KiB

Open AccessShort Note

6-Chloro-3-nitro-2-[(phenylsulfonyl)methyl]imidazo[1,2-b]pyridazine

by Romain Paoli-Lombardo, Nicolas Primas, Sébastien Hutter, Sandra Bourgeade-Delmas, Clotilde Boudot, Caroline Castera-Ducros, Inès Jacquet, Bertrand Courtioux, Nadine Azas, Pascal Rathelot and Patrice Vanelle

Molbank 2023, 2023(1), M1573; https://doi.org/10.3390/M1573 - 01 Feb 2023

Viewed by 1224

Abstract

As part of our ongoing scaffold-hopping work on an antikinetoplastid 3-nitroimidazo[1,2-a]pyridine scaffold, we explored 3-nitroimidazo[1,2-b]pyridazine as a potential new antikinetoplastid series. Using conditions previously described by our lab, we obtained 6-chloro-3-nitro-2-[(phenylsulfonyl)methyl]imidazo[1,2-b]pyridazine with 54% yield. In vitro activity [...] Read more.

As part of our ongoing scaffold-hopping work on an antikinetoplastid 3-nitroimidazo[1,2-a]pyridine scaffold, we explored 3-nitroimidazo[1,2-b]pyridazine as a potential new antikinetoplastid series. Using conditions previously described by our lab, we obtained 6-chloro-3-nitro-2-[(phenylsulfonyl)methyl]imidazo[1,2-b]pyridazine with 54% yield. In vitro activity of this compound was evaluated against both the promastigote form of Leishmania donovani, the axenic amastigote form of Leishmania infantum and the trypomastigote blood stream form of Trypanosomabrucei brucei, and its influence on cell viability was assessed on the HepG2 cell line. However, despite good activity against the trypomastigote blood stream form of T. b. brucei (EC₅₀ = 0.38 µM), it showed poor solubility in both HepG2 (CC₅₀ > 7.8 µM) and L. infantum axenic amastigotes (EC₅₀ > 1.6 µM) culture media, associated with a loss of activity against the promastigote form of L. infantum (EC₅₀ > 15.6 µM). Full article

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Figure 1

6 pages, 1118 KiB

Open AccessCommunication

(3-(1H-Indol-3-yl)-2-(7,8,12,13-tetraoxa-10-azaspiro[5.7]tridecan-10-yl)propanoic acid) with Cytotoxic Activity

by Nataliya N. Makhmudiyarova, Irina R. Ishmukhametova, Lilya U. Dzhemileva and Usein M. Dzhemilev

Molbank 2023, 2023(1), M1572; https://doi.org/10.3390/M1572 - 01 Feb 2023

Viewed by 1042

Abstract

An efficient method for the synthesis of 3-(1H-indol-3-yl)-2-(7,8,12,13-tetraoxa-10-azaspiro[5.7]tridecan-10-yl)propanoic acid) via condensation of 7,8,10,12,13-pentaoxaspiro[5.7]tridecane with tryptophan under the action of a catalyst based on Sm(NO₃)₃·6H₂O has been developed. A high cytotoxic activity of eight-membered azadiperoxide against [...] Read more.

An efficient method for the synthesis of 3-(1H-indol-3-yl)-2-(7,8,12,13-tetraoxa-10-azaspiro[5.7]tridecan-10-yl)propanoic acid) via condensation of 7,8,10,12,13-pentaoxaspiro[5.7]tridecane with tryptophan under the action of a catalyst based on Sm(NO₃)₃·6H₂O has been developed. A high cytotoxic activity of eight-membered azadiperoxide against tumor cells Jurkat, K562, U937, and HL60 was established. Additionally, this compound is an inducer of apoptosis and affects the cell cycle. Full article

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Figure 1

4 pages, 523 KiB

Open AccessShort Note

2-{9-(10-Bromoanthracenyl)}-1,3-dihydro-1H-[d]-1,3,2-benzodiazaborole

by Siphamandla Sithebe

Molbank 2023, 2023(1), M1569; https://doi.org/10.3390/M1569 - 27 Jan 2023

Viewed by 1021

Abstract

In this paper, a synthesis and characterization of a novel three coordinate 2-{9-(10-Bromoanthracenyl)}-1,3-dihydro-1H-[d]-1,3,2-benzodiazaborole from a cyclo-condensation reaction of o-phenylenediamine and 10-bromoanthracene-9-boronic acid is described. The desired product was obtained in 0.343 g (92% yields) with its structure characterized [...] Read more.

In this paper, a synthesis and characterization of a novel three coordinate 2-{9-(10-Bromoanthracenyl)}-1,3-dihydro-1H-[d]-1,3,2-benzodiazaborole from a cyclo-condensation reaction of o-phenylenediamine and 10-bromoanthracene-9-boronic acid is described. The desired product was obtained in 0.343 g (92% yields) with its structure characterized by ¹H, ¹¹B, ¹³C NMR, HRMS and FT-IR. Full article

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Scheme 1

7 pages, 762 KiB

Open AccessCommunication

Synthesis of Pentacycloundecane (PCUD) Based Spiro-Pyrano-Cage Framework via Ring-Closing Metathesis

by Sambasivarao Kotha, Mohammad Salman and Subba Rao Cheekatla

Molbank 2023, 2023(1), M1567; https://doi.org/10.3390/M1567 - 23 Jan 2023

Cited by 1 | Viewed by 1436

Abstract

Here, we demonstrate a short synthetic route to pyrano cage systems containing pentacycloundecane units by employing ring-closing metathesis (RCM) as a key step. These cage systems were constructed starting with readily available starting materials by adopting atomic economic processes such as cycloadditions (Diels-Alder [...] Read more.

Here, we demonstrate a short synthetic route to pyrano cage systems containing pentacycloundecane units by employing ring-closing metathesis (RCM) as a key step. These cage systems were constructed starting with readily available starting materials by adopting atomic economic processes such as cycloadditions (Diels-Alder reaction and [2+2] cycloaddition), Grignard addition, and olefin metathesis. The key building block, such as hexacyclic cage dione, was prepared from 1,4-naphthoquinone derivative and freshly cracked 1,3-cyclopentadiene. Some of these heterocyclic motifs are useful in biological chemistry and valuable as key synthons for high-energy-density materials. Full article

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Figure 1

7 pages, 720 KiB

Open AccessCommunication

Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free Conditions

by Roman D. Marchenko and Andrei S. Potapov

Molbank 2023, 2023(1), M1551; https://doi.org/10.3390/M1551 - 13 Jan 2023

Viewed by 1261

Abstract

Nucleophilic substitution reactions between 1,2,3-triazole and dibromomethane or 1,2-dirbomoethane in a superbasic medium potassium hydroxide–dimethyl sulfoxide gave mixtures of the isomeric bis(1,2,3-triazolyl)alkanes, in which (1,2,3-triazol-1-yl)(1,2,3-triazol-2-yl)alkanes and bis(1,2,3-triazol-2-yl)alkanes were the dominating products, while bis(triazol-1-yl)alkanes were detected only in trace amounts. The same products could [...] Read more.

Nucleophilic substitution reactions between 1,2,3-triazole and dibromomethane or 1,2-dirbomoethane in a superbasic medium potassium hydroxide–dimethyl sulfoxide gave mixtures of the isomeric bis(1,2,3-triazolyl)alkanes, in which (1,2,3-triazol-1-yl)(1,2,3-triazol-2-yl)alkanes and bis(1,2,3-triazol-2-yl)alkanes were the dominating products, while bis(triazol-1-yl)alkanes were detected only in trace amounts. The same products could also be obtained under solvent-free conditions in a neat reaction mixture. The proposed methods are economically feasible, do not require using toxic solvents or catalysts, and make the (1,2,3-triazol-2-yl)-derivatives, inaccessible by alkyne-azide cycloaddition (click) reactions, readily available. Full article

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Graphical abstract

8 pages, 1542 KiB

Open AccessShort Note

2,4-Diamino-5-(5-hydroxy-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile

by Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Oleg I. Maslov and Michail N. Elinson

Molbank 2023, 2023(1), M1541; https://doi.org/10.3390/M1541 - 09 Jan 2023

Viewed by 1202

Abstract

5H-Chromeno[2,3-b]pyridines are important compounds with industrial, biological, and medicinal properties. In this short note, the multicomponent reaction of salicylaldehyde, malononitrile dimer, and 2-phenyl-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one in dimethyl sulfoxide at ambient temperature was investigated to give 2,4-diamino-5-(5-hydroxy-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-5H [...] Read more.

5H-Chromeno[2,3-b]pyridines are important compounds with industrial, biological, and medicinal properties. In this short note, the multicomponent reaction of salicylaldehyde, malononitrile dimer, and 2-phenyl-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one in dimethyl sulfoxide at ambient temperature was investigated to give 2,4-diamino-5-(5-hydroxy-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile with good yield. The structure of the previously unknown chromeno[2,3-b]pyridine derivative was confirmed by elemental analysis, mass, nuclear magnetic resonance, and infrared spectroscopy data. The ADME (absorption, distribution, metabolism, and excretion) properties were also assessed. Full article

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Graphical abstract

2022

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6 pages, 1729 KiB

Open AccessShort Note

2-[2-(Diphenylphosphoryl)phenyl]-1H-perimidine

by Mangaliso N. Goge, Siphamandla Sithebe and Tshephiso R. Papo

Molbank 2023, 2023(1), M1537; https://doi.org/10.3390/M1537 - 29 Dec 2022

Cited by 1 | Viewed by 1314

Abstract

In this paper, we report the crystal structure of 2-[2-(diphenylphosphoryl)phenyl]-1H-perimidine (L1) obtained from the ring closure reaction of 1,8-diaminonaphthalene and 2-(diphenylphosphino)benzaldehyde, followed by the dehydrogenation reaction with sodium metabisulfite (Na₂S₂O₅). L1 was characterised using ¹H, ¹³ [...] Read more.

In this paper, we report the crystal structure of 2-[2-(diphenylphosphoryl)phenyl]-1H-perimidine (L1) obtained from the ring closure reaction of 1,8-diaminonaphthalene and 2-(diphenylphosphino)benzaldehyde, followed by the dehydrogenation reaction with sodium metabisulfite (Na₂S₂O₅). L1 was characterised using ¹H, ¹³C & ³¹P NMR, FT-IR and X-ray single structure analyses. Full article

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Figure 1

5 pages, 1992 KiB

Open AccessCommunication

1-(4-{[3,5-bis({[3,5-Dimethyl-4-(4-methyl-3,5-dioxo-1,2,4-triazolidin-1-yl)-phenoxy]methyl})phenyl]methoxy}-2,6-dimethyl-phenyl)-4-methyl-1,2,4-triazolidine-3,5-dione

by Gary W. Breton and James Alexander Bowron, Jr.

Molbank 2023, 2023(1), M1535; https://doi.org/10.3390/M1535 - 27 Dec 2022

Cited by 1 | Viewed by 1032

Abstract

Appropriately substituted N-centered urazolyl radicals are capable of generating interesting cage-like structures upon forming N-N bonds. The radicals are generated by the oxidation of the corresponding NH urazole precursors. We synthesized a triurazole precursor that we hoped would dimerize through the formation of [...] Read more.

Appropriately substituted N-centered urazolyl radicals are capable of generating interesting cage-like structures upon forming N-N bonds. The radicals are generated by the oxidation of the corresponding NH urazole precursors. We synthesized a triurazole precursor that we hoped would dimerize through the formation of three N-N bonds to afford a large molecular cage. Unfortunately, the attempts at the oxidation of the urazoles to form urazolyl radicals instead only lead to random oligomerization, forming plastic-like materials rather than the desired cages. Full article

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Figure 1

9 pages, 838 KiB

Open AccessShort Note

1-[2-(1H-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)urea

by Antonia G. Sarantou and George Varvounis

Molbank 2023, 2023(1), M1531; https://doi.org/10.3390/M1531 - 22 Dec 2022

Viewed by 1581

Abstract

For the synthesis of 1-(2-(1H-pyrrole-2-carbonyl)phenyl)-3-(4-methoxyphenyl)urea, the final product, two different methods were used, in one or two steps, from (2-aminophenyl)(1H-pyrrol-2-yl)methanone. The one-step synthesis entailed a carbonylation reaction with 1/3 equivalent of triphosgene in the presence of two equivalents of [...] Read more.

For the synthesis of 1-(2-(1H-pyrrole-2-carbonyl)phenyl)-3-(4-methoxyphenyl)urea, the final product, two different methods were used, in one or two steps, from (2-aminophenyl)(1H-pyrrol-2-yl)methanone. The one-step synthesis entailed a carbonylation reaction with 1/3 equivalent of triphosgene in the presence of two equivalents of trimethylamine, followed by the addition of 4-methoxyaniline to the in situ generated aryl isocyanate. The two-step synthesis required first the preparation of phenyl(2-(1H-pyrrole-2-carbonyl)phenyl)carbamate and then a substitution reaction by 4-methoxyaniline. The first method produced the final product in 72% yield, which was the best yield. The structure of the final product was confirmed by FTIR, UV-VIS, ¹H and ¹³C NMR spectroscopy and high resolution mass spectrometry. Full article

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Figure 1

7 pages, 729 KiB

Open AccessShort Note

2-Benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

by Ivette Morales-Salazar, Mónica A. Rincón-Guevara, Eduardo González-Zamora and Alejandro Islas-Jácome

Molbank 2022, 2022(4), M1503; https://doi.org/10.3390/M1503 - 23 Nov 2022

Cited by 1 | Viewed by 1142

Abstract

The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (1) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade aza-Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the [...] Read more.

The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (1) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade aza-Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the Lewis acid catalyst, and microwave-dielectric heating to increase the overall yield by up to 73%, while decreasing the reaction time to less than one hour. Product 1 was fully characterized by its physicochemical properties and using spectroscopic techniques (IR, HRMS and NMR). Full article

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Graphical abstract

7 pages, 1786 KiB

Open AccessShort Note

4-Methyl-7-((2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)ethyl)thio)-coumarin

by Vanya Kurteva, Rusi Rusew and Boris Shivachev

Molbank 2022, 2022(4), M1491; https://doi.org/10.3390/M1491 - 12 Nov 2022

Viewed by 1417

Abstract

The novel compound 4-methyl-7-((2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)ethyl)thio)-coumarin is obtained in good yield via a two-step protocol; that is, initial synthesis of the reagent 2-((2-chloroethyl)thio)-5-methyl-1,3,4-thiadiazole followed by alkylation of 7-mercapto-4-methylcoumarin. The product’s structure is assigned by 1D and 2D NMR experiments and is confirmed by single-crystal XRD. [...] Read more.

The novel compound 4-methyl-7-((2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)ethyl)thio)-coumarin is obtained in good yield via a two-step protocol; that is, initial synthesis of the reagent 2-((2-chloroethyl)thio)-5-methyl-1,3,4-thiadiazole followed by alkylation of 7-mercapto-4-methylcoumarin. The product’s structure is assigned by 1D and 2D NMR experiments and is confirmed by single-crystal XRD. Full article

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Figure 1

6 pages, 812 KiB

Open AccessShort Note

5-Chloro-6-oxo-6H-xantheno[4,3-d]thiazole-2-carbonitrile

by Konstantinos Paraskevas, Christos Iliopoulos-Tsoutsouvas, Eleftheria A. Georgiou and Ioannis K. Kostakis

Molbank 2022, 2022(4), M1489; https://doi.org/10.3390/M1489 - 10 Nov 2022

Viewed by 1439

Abstract

Xanthones and benzothiazoles are important classes of heterocyclic compounds with versatile biological activities. Herein, we describe a straightforward and scalable synthesis of 5-chloro-6-oxo-6H-xantheno[4,3-d]thiazole-2-carbonitrile, a thiazole-fused xanthone, via a six-step approach, using Appel’s salt for the synthesis of the thiazole [...] Read more.

Xanthones and benzothiazoles are important classes of heterocyclic compounds with versatile biological activities. Herein, we describe a straightforward and scalable synthesis of 5-chloro-6-oxo-6H-xantheno[4,3-d]thiazole-2-carbonitrile, a thiazole-fused xanthone, via a six-step approach, using Appel’s salt for the synthesis of the thiazole ring. The thiazole-fused xanthone was fully characterized employing ¹H and ¹³C NMR spectra, using direct and long-range heteronuclear correlation experiments (HMBC and HMQC). Full article

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Graphical abstract

8 pages, 2368 KiB

Open AccessCommunication

Synthesis and Characterization of 3-Methyl-1-(4-(trifluoromethyl)phenyl)indeno [1,2-c]pyrazol-4(1H)-one

by Linh Lam, Sang H. Park and Joseph Sloop

Molbank 2022, 2022(4), M1483; https://doi.org/10.3390/M1483 - 07 Nov 2022

Viewed by 1749

Abstract

Pyrazoles have potential applications in the agrochemical and medicinal chemistry industries as pesticides, anti-inflammatory medications, and antitumor drugs. Fluorinated fused-ring pyrazoles may also possess medicinally useful properties. Herein, we report the acid-catalyzed synthesis of a new tricyclic, trifluoromethylated indenopyrazole, 3-methyl-1-(4-(trifluoromethyl)phenyl)indeno[1,2-c]pyrazol-4(1H)-one, from [...] Read more.

Pyrazoles have potential applications in the agrochemical and medicinal chemistry industries as pesticides, anti-inflammatory medications, and antitumor drugs. Fluorinated fused-ring pyrazoles may also possess medicinally useful properties. Herein, we report the acid-catalyzed synthesis of a new tricyclic, trifluoromethylated indenopyrazole, 3-methyl-1-(4-(trifluoromethyl)phenyl)indeno[1,2-c]pyrazol-4(1H)-one, from 2-acetyl-1,3-indanedione and 4-trifluoromethylphenylhydrazine. This isomeric pyrazole was obtained in yields ranging from 4–24%. NMR spectroscopic characterization and elemental analysis support the structural assignment, identity, and purity of the product. Full article

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4 pages, 2070 KiB

Open AccessShort Note

Dimethyl 3,7-diamino-4,8-bis((2-methoxy-2-oxoethyl)thio)benzo[1,2-b:4,5-b’]dithiophene-2,6-dicarboxylate

by Branislav Pavilek, Daniel Végh, Dušan Bortňák, Veronika Šmejkalová, Jozef Kožíšek and Viktor Milata

Molbank 2022, 2022(4), M1474; https://doi.org/10.3390/M1474 - 27 Oct 2022

Viewed by 1192

Abstract

The convenient and multigram synthesis of a linear benzo[b]dithiophene (BDT) structure is proposed (dimethyl 3,7-diamino-4,8-bis((2-methoxy-2-oxoethyl)thio)benzo[1,2-b:4,5-b’]dithiophene-2,6-dicarboxylate). The starting materials are commercially available 2,3,5,6-tetrachloroterephthalonitrile and methyl 2-mercaptoacetate, which undergo aromatic substitution, followed by a cyclization reaction in basic conditions [...] Read more.

The convenient and multigram synthesis of a linear benzo[b]dithiophene (BDT) structure is proposed (dimethyl 3,7-diamino-4,8-bis((2-methoxy-2-oxoethyl)thio)benzo[1,2-b:4,5-b’]dithiophene-2,6-dicarboxylate). The starting materials are commercially available 2,3,5,6-tetrachloroterephthalonitrile and methyl 2-mercaptoacetate, which undergo aromatic substitution, followed by a cyclization reaction in basic conditions to form suitable BDT for potential optoelectronic applications. Full article

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4 pages, 577 KiB

Open AccessShort Note

1-Phenyl-3-tosyl-1H-pyrrole

by Zoumpoulia Kechagioglou and Vassilis J. Demopoulos

Molbank 2022, 2022(4), M1471; https://doi.org/10.3390/M1471 - 26 Oct 2022

Viewed by 1123

Abstract

1-Phenyl-3-tosyl-1H-pyrrole was prepared, in moderate yield, by the electrophilic aromatic substitution of 1-phenyl-1H-pyrrole with tosyl chloride in the presence of excess zinc oxide under solvent-free conditions. A minor product was its isomer, 1-phenyl-2-tosyl-1H-pyrrole. Full article

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Scheme 1

7 pages, 738 KiB

Open AccessShort Note

3-Methyl 5-{3-[(4-Methylbenzenesulfonyl)oxy]propyl} 4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

by Carlotta Borgarelli, Stijn Lenaers, Wim M. De Borggraeve and Ermal Ismalaj

Molbank 2022, 2022(4), M1460; https://doi.org/10.3390/M1460 - 09 Oct 2022

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Abstract

The 1,4-dihydropyridine is a ubiquitous scaffold employed not only in medicinal chemistry but also in organic synthesis, given its ability to act as a hydrogen transfer reagent, thus emulating NAD(P)H reducing agents. In this work, we describe the synthesis of 3-methyl 5-{3-[(4-methylbenzenesulfonyl)oxy]propyl} 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate [...] Read more.

The 1,4-dihydropyridine is a ubiquitous scaffold employed not only in medicinal chemistry but also in organic synthesis, given its ability to act as a hydrogen transfer reagent, thus emulating NAD(P)H reducing agents. In this work, we describe the synthesis of 3-methyl 5-{3-[(4-methylbenzenesulfonyl)oxy]propyl} 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate as scaffold, which enables downstream derivatization towards new 1,4-dihydropyridine molecules. Inspired by the literature, a new two-step synthesis was planned that involved: (i) synthesis of a silylated 1,4-dihydropyridine derivative and (ii) deprotection and tosylation in one step using tosyl fluoride. Full article

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6 pages, 661 KiB

Open AccessShort Note

Ferrocenyl-bis-(1-(4-benzyl-5-morpholinooxazol-2-yl)-N-(4-(trifluoromethyl)benzyl)methanamine)

by Roberto E. Blanco-Carapia, Enrique A. Aguilar-Rangel, Alejandro Islas-Jácome and Eduardo González-Zamora

Molbank 2022, 2022(3), M1444; https://doi.org/10.3390/M1444 - 13 Sep 2022

Cited by 1 | Viewed by 1329

Abstract

The new bis-heterocyclic compound ferrocenyl-bis-(1-(4-benzyl-5-morpholinooxazol-2-yl)-N-(4-(trifluoromethyl)benzyl)methanamine) (1) was synthesized in 73% overall yield in 1.5 hours via a pseudo-repetitive Ugi-Zhu five-component reaction, starting from 1,1′-ferrocenedicarboxaldehyde, 4-(trifluoromethyl)benzylamine, and 2-isocyano-1-morpholino-3-phenylpropan-1-one, in 1:2.1:2.2 proportions, respectively, using scandium(III) triflate as a [...] Read more.

The new bis-heterocyclic compound ferrocenyl-bis-(1-(4-benzyl-5-morpholinooxazol-2-yl)-N-(4-(trifluoromethyl)benzyl)methanamine) (1) was synthesized in 73% overall yield in 1.5 hours via a pseudo-repetitive Ugi-Zhu five-component reaction, starting from 1,1′-ferrocenedicarboxaldehyde, 4-(trifluoromethyl)benzylamine, and 2-isocyano-1-morpholino-3-phenylpropan-1-one, in 1:2.1:2.2 proportions, respectively, using scandium(III) triflate as a Lewis-acid catalyst, microwaves as a heat source, and toluene as a solvent. The synthesized compound was characterized by 1D (¹H, ¹³C, and ¹⁹F) and 2D (COSY, HSQC, and HMBC) NMR, HRMS, and FT-IR. Full article

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9 pages, 612 KiB

Open AccessShort Note

1,1′-{[3,5-Bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] Dibromide

by Reinis Ozolins, Mara Plotniece, Karlis Pajuste, Reinis Putralis, Nadiia Pikun, Arkadij Sobolev, Aiva Plotniece and Martins Rucins

Molbank 2022, 2022(3), M1438; https://doi.org/10.3390/M1438 - 02 Sep 2022

Cited by 3 | Viewed by 1694

Abstract

A synthesis of a cationic moiety and fluorescent moieties containing amphiphilic 1,4-dihydropyridine (1,4-DHP) derivatives was performed starting with the Hantzsch-type cyclization of dodecyl acetoacetate, phenylaldehyde and ammonium acetate. Bromination of the 2,6-dimethyl groups of a parent 1,4-DHP compound, followed by nucleophilic substitution of [...] Read more.

A synthesis of a cationic moiety and fluorescent moieties containing amphiphilic 1,4-dihydropyridine (1,4-DHP) derivatives was performed starting with the Hantzsch-type cyclization of dodecyl acetoacetate, phenylaldehyde and ammonium acetate. Bromination of the 2,6-dimethyl groups of a parent 1,4-DHP compound, followed by nucleophilic substitution of bromine with 4-(anthracen-9-yl)pyridine, produced the desired 1,1′-{[3,5-bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] dibromide. The obtained target compound was fully characterized by the IR, ¹H NMR, ¹³C NMR and HRMS data. Studies of the self-assembling properties and characterization of the nanoparticles obtained by the ethanol injection method were performed using dynamic light scattering (DLS) measurements. DLS measurement data showed that 1,1′-{[3,5-bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] dibromide produced liposomes that had average diameters of 200 nm when the samples were freshly prepared, and 140 nm after 7 days or 1 month storage. The PDI values of the samples were approximately 0.50 and their zeta-potential values were approximately 41 mV when the samples were freshly prepared, and 33 mV after storage. The obtained nanoparticles were stored at room temperature for one month and remained stable during that period. The mean molecular area of the cationic 1,4-DHP-anthracene hybrid 4 was 118 Å², while the mean molecular area of the cationic 1,4-DHP 5 without anthracene substituents was only 83 Å². The photoluminescence quantum yield (PLQY) value for the EtOH solution of the 1,4-DHP derivative 4 was 10.8%, but for the 1,4-DHP derivative 5 it was only 1.8%. These types of compounds could be used as synthetic lipids in the further development of prospective theranostic delivery systems. Full article

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4 pages, 926 KiB

Open AccessShort Note

3-(1-Cyclohexyl-2-(cyclohexylamino)-4-(4-ethoxyphenyl)-6-oxo-1,6-dihydropyrimidin-5-yl)-1-methylquinoxalin-2(1H)-one

by Ekaterina E. Khramtsova, Svetlana O. Kasatkina, Maksim V. Dmitriev and Andrey N. Maslivets

Molbank 2022, 2022(3), M1421; https://doi.org/10.3390/M1421 - 05 Aug 2022

Viewed by 1624

Abstract

The reaction of 3-cyclohexyl-2-(cyclohexylimino)-6-(4-ethoxyphenyl)-5-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)-2,3-dihydro-4H-1,3-oxazin-4-one with ammonium acetate afforded 3-(1-cyclohexyl-2-(cyclohexylamino)-4-(4-ethoxyphenyl)-6-oxo-1,6-dihydropyrimidin-5-yl)-1-methylquinoxalin-2(1H)-one in a good yield. The compound was fully characterized. Full article

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4 pages, 1408 KiB

Open AccessShort Note

12H-Dibenzo[d,g][1,2,3]triselenocin-12-ol

by Marko Boskovic, Stanislav Andreev, Dieter Schollmeyer and Pierre Koch

Molbank 2022, 2022(3), M1418; https://doi.org/10.3390/M1418 - 01 Aug 2022

Viewed by 1324

Abstract

Reaction of diphenylmethanol (4) with n-butyllithium and subsequent treatment with selenium resulted in 12H-dibenzo[d,g][1,2,3]triselenocin-12-ol (5) comprising a novel heterocyclic ring system. The title compound 5 was analyzed by ¹H-NMR, ¹³C-NMR [...] Read more.

Reaction of diphenylmethanol (4) with n-butyllithium and subsequent treatment with selenium resulted in 12H-dibenzo[d,g][1,2,3]triselenocin-12-ol (5) comprising a novel heterocyclic ring system. The title compound 5 was analyzed by ¹H-NMR, ¹³C-NMR and HPLC. Additionally, the structure of 5 was confirmed by single crystal X-ray diffraction. Full article

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9 pages, 2000 KiB

Open AccessShort Note

3-Amino-4-(diphenylamino)-1H-2-benzopyran-1-one

by Felipe Quiroga-Suavita, Ricaurte Rodríguez and Omar León

Molbank 2022, 2022(3), M1408; https://doi.org/10.3390/M1408 - 14 Jul 2022

Viewed by 1463

Abstract

Various synthetic methodologies to obtain 3,4-diaminoisocumarin nucleus have been reported and described. However, mechanistic analysis based on experimental evidence is lacking. Herein, we report the synthesis of the novel 3-amino-4-(diphenylamino)-1H-2-benzopyran-1-one using a two-step methodology with a new mechanistic proposal to explain [...] Read more.

Various synthetic methodologies to obtain 3,4-diaminoisocumarin nucleus have been reported and described. However, mechanistic analysis based on experimental evidence is lacking. Herein, we report the synthesis of the novel 3-amino-4-(diphenylamino)-1H-2-benzopyran-1-one using a two-step methodology with a new mechanistic proposal to explain the formation of the latter based on previously reported precursors and the established conditions. This compound was afforded in 80% yield. Full article

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Graphical abstract

7 pages, 2059 KiB

Open AccessCommunication

Unexpected Formation of 4-[(1-Carbamoyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl)amino]benzoic Acid from 4-[(3-Amino-1-oxo-1H-2-benzopyran-4-yl)amino]benzoic Acid

by Ricaurte Rodríguez, Felipe Quiroga-Suavita and Mónica Yadira Dotor Robayo

Molbank 2022, 2022(3), M1407; https://doi.org/10.3390/M1407 - 12 Jul 2022

Viewed by 1487

Abstract

With the aim of obtaining derivatives belonging to 2′,3′-diphenyl-3H-spiro[[2]benzofuran-1,4′-imidazole]-3,5′(3′H)-dione nucleus, we synthesized 4-[(3-amino-1-oxo-1H-2-benzopyran-4-yl)amino]benzoic acid (a 3,4-diaminoisocoumarine derivative), a known precursor of 4-[(1-carbamoyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl)amino]benzoic acid (a phthalide–carboxamide-bearing system) by a novel methodology that we report here. The reaction conditions [...] Read more.

With the aim of obtaining derivatives belonging to 2′,3′-diphenyl-3H-spiro[[2]benzofuran-1,4′-imidazole]-3,5′(3′H)-dione nucleus, we synthesized 4-[(3-amino-1-oxo-1H-2-benzopyran-4-yl)amino]benzoic acid (a 3,4-diaminoisocoumarine derivative), a known precursor of 4-[(1-carbamoyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl)amino]benzoic acid (a phthalide–carboxamide-bearing system) by a novel methodology that we report here. The reaction conditions were optimized to afford the latter in 62% yield. Full article

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8 pages, 553 KiB

Open AccessCommunication

Synthesis and Evaluation of Self-Assembling Properties of 3-(3,5-Difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium Iodides

by Nadiia Pikun, Davis Lacis, Arkadij Sobolev, Martins Rucins, Mara Plotniece, Karlis Pajuste and Aiva Plotniece

Molbank 2022, 2022(3), M1402; https://doi.org/10.3390/M1402 - 06 Jul 2022

Viewed by 1574

Abstract

A synthesis of 3-(3,5-difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodides with ethyl or nonyl ester groups at positions 3 and 5 was performed. Treatment of the corresponding 2’,6’-dimethyl-1’,4’-dihydro-[3,4’-bipyridine]-3’,5’-dicarboxylates with Selectfluor^® followed by quaternization of pyridine moiety in the obtained dialkyl 2,4-diacetyl-2,4-difluoro-3-(pyridin-3-yl)pentanedioates with methyl iodide gave the desired [...] Read more.

A synthesis of 3-(3,5-difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodides with ethyl or nonyl ester groups at positions 3 and 5 was performed. Treatment of the corresponding 2’,6’-dimethyl-1’,4’-dihydro-[3,4’-bipyridine]-3’,5’-dicarboxylates with Selectfluor^® followed by quaternization of pyridine moiety in the obtained dialkyl 2,4-diacetyl-2,4-difluoro-3-(pyridin-3-yl)pentanedioates with methyl iodide gave the desired 3-(3,5-difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodides. This type of compound would be useful as synthetic lipids for further development of the delivery systems. The obtained target compounds were fully characterized by ¹H NMR, ¹⁹F NMR, ¹³C NMR, HRMS, IR and UV data. The estimation of self-assembling properties and characterization of the nanoparticles obtained by ethanol solution injection in an aqueous media were performed by dynamic light scattering (DLS) measurements. DLS measurement data showed that 3-(3,5-difluoro-3,5-bis((nonyloxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodide created liposomes with the average diameter of 300–400 nm and polydispersity index (PDI) value around 0.30–0.40, while 3-(3,5-difluoro-3,5-bis((ethyloxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodide formed a heterogeneous sample with PDI value 1, which was not prospective for delivery system development. Full article

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Scheme 1

5 pages, 2334 KiB

Open AccessCommunication

Styryl Hemicyanine Dye (E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium Iodide for Nucleic Acids and Cell Nucleoli Visualization

by Aleksey A. Vasilev, Marina Miteva, Nikolay Ishkitiev, Maria Dragneva, Lora Topalova and Meglena I. Kandinska

Molbank 2022, 2022(2), M1392; https://doi.org/10.3390/M1392 - 20 Jun 2022

Cited by 2 | Viewed by 2106

Abstract

(E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide 1 was prepared by a convenient and reliable reaction procedure. The slight molar excess of the starting benzaldehyde and the mixture of ethanol: ethyl acetate in the ratio 3:1 as a solvent afforded a pure reaction product. The photophysical [...] Read more.

(E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide 1 was prepared by a convenient and reliable reaction procedure. The slight molar excess of the starting benzaldehyde and the mixture of ethanol: ethyl acetate in the ratio 3:1 as a solvent afforded a pure reaction product. The photophysical properties of the dye in a TE buffer in the absence and presence of double-stranded DNA (dsDNA) were elucidated. The low intrinsic fluorescence of 1 in TE buffer is followed by an increase in the fluorescence after dsDNA binding. The dye is nontoxic for stem cells from apical papilla and the most concentrated fluorescence is detected in the cell nucleoli. Full article

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Graphical abstract

7 pages, 859 KiB

Open AccessCommunication

Synthesis, Crystal Structure and Anti-Leukemic Activity of 1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one

by Jean Guillon, Solène Savrimoutou, Sandra Albenque-Rubio, Noël Pinaud, Stéphane Moreau and Vanessa Desplat

Molbank 2022, 2022(1), M1333; https://doi.org/10.3390/M1333 - 09 Feb 2022

Cited by 4 | Viewed by 1912

Abstract

1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one has been synthesized through a multi-step pathway starting from commercially available 2-nitroaniline. A structure characterization of this new substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, ¹H-NMR, ¹³C-NMR, X-Ray and HRMS spectral analysis. This [...] Read more.

1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one has been synthesized through a multi-step pathway starting from commercially available 2-nitroaniline. A structure characterization of this new substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, ¹H-NMR, ¹³C-NMR, X-Ray and HRMS spectral analysis. This new pyrroloquinoxaline derivative shows an interesting cytotoxic potential against several human leukemia cell lines (HL60, K562 and U937 cells). Full article

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2021

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7 pages, 2131 KiB

Open AccessCommunication

CF₃-Bis-TEMPO-Vis: New Visible Light Active Bis-Benzimidazolequinone Alkoxyamine

by Patrick Kielty, Pau Farràs, Dennis A. Smith and Fawaz Aldabbagh

Molbank 2021, 2021(4), M1300; https://doi.org/10.3390/M1300 - 26 Nov 2021

Viewed by 2159

Abstract

Alkoxyamines of TEMPO usually dissociate thermally at >100 °C; however, room temperature homolysis, activated by visible light, occurs with benzimidazolequinone derivatives. 1,1’-Dimethyl-2,2’-bis{[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]methyl}-6-(trifluoromethyl)-1H,1’H-[5,5’-bibenzimidazole]-4,4’,7,7’-tetrone (CF₃-Bis-TEMPO-Vis) is prepared in a 59% yield through NBS/H₂SO₄ oxidative [...] Read more.

Alkoxyamines of TEMPO usually dissociate thermally at >100 °C; however, room temperature homolysis, activated by visible light, occurs with benzimidazolequinone derivatives. 1,1’-Dimethyl-2,2’-bis{[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]methyl}-6-(trifluoromethyl)-1H,1’H-[5,5’-bibenzimidazole]-4,4’,7,7’-tetrone (CF₃-Bis-TEMPO-Vis) is prepared in a 59% yield through NBS/H₂SO₄ oxidative demethylations of the dimethoxybenzimidazole-benzimidazolequinone precursor with aqueous work up. The alternative basic work up in air gave the epoxide derivative of CF₃-Bis-TEMPO-Vis. Unlike the latter CF₃-epoxide, both alkoxyamine residues are labile under green light (470–600 nm), and the rate of TEMPO release is three times slower than Bis-TEMPO-Vis. Full article

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5 pages, 542 KiB

Open AccessCommunication

Regioselective Synthesis of 4-Bromo-3-formyl-N-phenyl-5-propylthiophene-2-carboxamide

by Sukanta Bar and Maxwell Israel Martin

Molbank 2021, 2021(4), M1296; https://doi.org/10.3390/M1296 - 16 Nov 2021

Cited by 1 | Viewed by 2104

Abstract

We synthesized 4-bromo-3-formyl-N-phenyl-5-propylthiophene-2-carboxamide by using three successive direct lithiations and a bromination reaction starting from thiophene. All these lithiation reactions were carried out at −78 °C to RT over a period of 1 to 24 h based on the reactivity of [...] Read more.

We synthesized 4-bromo-3-formyl-N-phenyl-5-propylthiophene-2-carboxamide by using three successive direct lithiations and a bromination reaction starting from thiophene. All these lithiation reactions were carried out at −78 °C to RT over a period of 1 to 24 h based on the reactivity of electrophile. This is a four-step protocol starting from thiophene with an overall yield of 47%. Full article

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Graphical abstract

4 pages, 369 KiB

Open AccessShort Note

4,7-Bis(1,2,3,4,4a,9a-Hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine

by Timofey N. Chmovzh, Karim S. Gaisin and Oleg A. Rakitin

Molbank 2021, 2021(4), M1295; https://doi.org/10.3390/M1295 - 05 Nov 2021

Cited by 2 | Viewed by 1876

Abstract

New donor-acceptor-donor (D-A-D)-type structures are widely used to design effective organic light-emitting diodes (OLEDs). In this communication, 4,7-bis(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine was obtained in a 65% yield by the treatment of 4,7-dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide with 2,3,4,4a,9,9a-hexahydro-1H-carbazole. The structure of [...] Read more.

New donor-acceptor-donor (D-A-D)-type structures are widely used to design effective organic light-emitting diodes (OLEDs). In this communication, 4,7-bis(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine was obtained in a 65% yield by the treatment of 4,7-dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide with 2,3,4,4a,9,9a-hexahydro-1H-carbazole. The structure of the newly synthesized compounds was established by means of an elemental analysis, ¹H, ¹³C NMR, IR and UV spectroscopy, and HRMS and LR mass-spectrometry. Full article

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5 pages, 560 KiB

Open AccessShort Note

6-(Chloromethyl)-N,1-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

by Vladimir A. Ogurtsov and Oleg A. Rakitin

Molbank 2021, 2021(4), M1294; https://doi.org/10.3390/M1294 - 01 Nov 2021

Cited by 1 | Viewed by 1997

Abstract

Functionally 4,6-disubstituted 1H-pyrazolo[3,4-d]pyrimidines are important compounds with various pharmacological activities. 1-Substituted 4-chloro-6-(chloromethyl)-1H-pyrazolo[3,4-d]pyrimidines are practically unexplored derivatives in this series. In this paper, it was shown that the nucleophilic substitution of 4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine [...] Read more.

Functionally 4,6-disubstituted 1H-pyrazolo[3,4-d]pyrimidines are important compounds with various pharmacological activities. 1-Substituted 4-chloro-6-(chloromethyl)-1H-pyrazolo[3,4-d]pyrimidines are practically unexplored derivatives in this series. In this paper, it was shown that the nucleophilic substitution of 4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine with methylamine produced selectively 4-substituted product, 6-(chloromethyl)-N,1-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine. The structure of the synthesized compound was established by elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C-NMR, and IR spectroscopy, mass-spectrometry, and X-ray analysis. Full article

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5 pages, 1293 KiB

Open AccessCommunication

Ambient-Temperature Synthesis of (E)-N-(3-(tert-Butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanimine

by Diana Becerra, Justo Cobo and Juan-Carlos Castillo

Molbank 2021, 2021(3), M1250; https://doi.org/10.3390/M1250 - 07 Jul 2021

Cited by 1 | Viewed by 2050

Abstract

We report the ambient-temperature synthesis of novel (E)-N-(3-(tert-butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanamine 3 in 81% yield by a condensation reaction between 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and 2-pyridinecarboxaldehyde 2 in methanol using magnesium sulfate as a drying agent. [...] Read more.

We report the ambient-temperature synthesis of novel (E)-N-(3-(tert-butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanamine 3 in 81% yield by a condensation reaction between 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and 2-pyridinecarboxaldehyde 2 in methanol using magnesium sulfate as a drying agent. The N-pyrazolyl imine 3 was full characterized by IR, 1D, and 2D NMR spectroscopy, mass spectrometry, and elemental analysis. Full article

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3 pages, 314 KiB

Open AccessShort Note

(2,3-Dihydro-1H-indol-5-ylmethyl)amine

by Vladimir A. Ogurtsov and Oleg A. Rakitin

Molbank 2021, 2021(3), M1248; https://doi.org/10.3390/M1248 - 05 Jul 2021

Viewed by 1941

Abstract

New (2,3-dihydro-1H-indol-5-ylmethyl)amine was synthesized from 2-((1-acetylindolin-5-yl)methyl)isoindoline-1,3-dione by simultaneous deprotection of phthalimide and acetyl groups. The structure of the newly synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C NMR and IR spectroscopy and mass-spectrometry. The resulting [...] Read more.

New (2,3-dihydro-1H-indol-5-ylmethyl)amine was synthesized from 2-((1-acetylindolin-5-yl)methyl)isoindoline-1,3-dione by simultaneous deprotection of phthalimide and acetyl groups. The structure of the newly synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C NMR and IR spectroscopy and mass-spectrometry. The resulting compound is a convenient intermediate for various disubstituted 1-(indolin-5-yl)methanamines, which may be of interest as substances with useful pharmacological properties. Full article

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Graphical abstract

6 pages, 1287 KiB

Open AccessShort Note

(E)-4-Oxo-3,4-dihydroquinazoline-2-carbaldehyde Oxime

by Andreas S. Kalogirou, Andreas Kourtellaris and Panayiotis A. Koutentis

Molbank 2021, 2021(2), M1233; https://doi.org/10.3390/M1233 - 11 Jun 2021

Viewed by 1954

Abstract

Reaction of 4-oxo-3,4-dihydroquinazoline-2-carbaldehyde with hydroxylamine hydrochloride (1.1 equiv) in the presence of K₂CO₃ (1 equiv) gave (E)-4-oxo-3,4-dihydroquinazoline-2-carbaldehyde oxime (8) in 58% yield. The compound was fully characterized and the conformation of the oxime was supported by single crystal x-ray diffractometry. Full article

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Graphical abstract

6 pages, 665 KiB

Open AccessShort Note

3-(tert-Butyl)-N-(4-methoxybenzyl)-1-methyl-1H-pyrazol-5-amine

by Diana Becerra, Hugo Rojas and Juan-Carlos Castillo

Molbank 2021, 2021(1), M1196; https://doi.org/10.3390/M1196 - 10 Mar 2021

Cited by 2 | Viewed by 2418

Abstract

We reported an efficient one-pot two-step synthesis of 3-(tert-butyl)-N-(4-methoxybenzyl)-1-methyl-1H-pyrazol-5-amine 3 in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and p-methoxybenzaldehyde 2. The one-pot reductive amination proceeded [...] Read more.

We reported an efficient one-pot two-step synthesis of 3-(tert-butyl)-N-(4-methoxybenzyl)-1-methyl-1H-pyrazol-5-amine 3 in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and p-methoxybenzaldehyde 2. The one-pot reductive amination proceeded by the formation in situ of the N-(5-pyrazolyl)imine 4 as key synthetic intermediate of other valuable pyrazole derivatives. This methodology is distinguished by its operational easiness, short reaction time, isolation and purification of the aldimine intermediate is not required. The structure of the synthesized N-heterocyclic amine 3 was fully characterized by FTIR-ATR, 1D and 2D NMR experiments, EIMS, and elemental analysis. Full article

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Graphical abstract

10 pages, 2085 KiB

Open AccessCommunication

Synthesis of 1,5-Disubstituted Tetrazoles in Aqueous Micelles at Room Temperature

by Mohammed Abdessalam, Madjid Ait Sidhoum, Fatima-Zohra Zradni and Hocine Ilikti

Molbank 2021, 2021(1), M1194; https://doi.org/10.3390/M1194 - 09 Mar 2021

Cited by 4 | Viewed by 2252

Abstract

The ongoing study is a Ugi-azide four-component reaction for the synthesis of 1,5-disubstituted tetrazole(1,5-DST), which involves an aldehyde, different amines, isocyanides, and as azide’s source the Trimethylsilylazide (TMSN₃), in water as solvent using as catalyst the tetradecyltrimethylammonium bromide (TTAB) with a [...] Read more.

The ongoing study is a Ugi-azide four-component reaction for the synthesis of 1,5-disubstituted tetrazole(1,5-DST), which involves an aldehyde, different amines, isocyanides, and as azide’s source the Trimethylsilylazide (TMSN₃), in water as solvent using as catalyst the tetradecyltrimethylammonium bromide (TTAB) with a load of (10% mole), which provides a hydrophobic micellar reaction site. This approach is a step toward a green chemistry reaction of 1,5 disubstituted tetrazole. A serie of 1, 5- disubstituted tetrazole was synthesized by engaging a large substrate scope, leading to yields between 43% and 56%, which are compared afterwards with those obtained with methanol as solvent. The results were confirmed by HRMS, IR, and 1D NMR experiments. Full article

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7 pages, 1459 KiB

Open AccessShort Note

Ethyl 1-Butyl-2-(2-hydroxy-4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate

by Reshma Sathyanarayana and Boja Poojary

Molbank 2021, 2021(1), M1192; https://doi.org/10.3390/M1192 - 24 Feb 2021

Viewed by 2252

Abstract

Ethyl 4-(butylamino)-3-nitrobenzoate upon “one-pot” nitro-reductive cyclization using sodium dithionite and substituted aldehyde in dimethyl sulphoxide affords ethyl 1-butyl-2-(2-hydroxy-4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate in an 87% yield. The structural characterization was determined by Fourier-transfer infrared spectroscopy (FT-IR), Proton nuclear magnetic resonance (¹H-NMR), [...] Read more.

Ethyl 4-(butylamino)-3-nitrobenzoate upon “one-pot” nitro-reductive cyclization using sodium dithionite and substituted aldehyde in dimethyl sulphoxide affords ethyl 1-butyl-2-(2-hydroxy-4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate in an 87% yield. The structural characterization was determined by Fourier-transfer infrared spectroscopy (FT-IR), Proton nuclear magnetic resonance (¹H-NMR), Carbon-13 nuclear magnetic resonance (¹³C-NMR), mass spectrometry, Ultraviolet-visible(UV-Vis), photoluminescence (PL), thin-film solid emission spectra, cyclic voltammetry (CV) and thermogravimetric (TGA) analysis. Molecular electrostatic potential (MEP) was studied to determine the reactive sites of the molecule. Full article

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5 pages, 907 KiB

Open AccessShort Note

2-Amino-5-chloro-1H-pyrrole-3,4-dicarbonitrile

by Andreas S. Kalogirou and Panayiotis A. Koutentis

Molbank 2021, 2021(1), M1191; https://doi.org/10.3390/M1191 - 13 Feb 2021

Cited by 1 | Viewed by 2608

Abstract

The reaction of tetracyanoethylene (TCNE) with HCl (g) in the presence of Sn (1 equiv) and AcOH resulted in 2-amino-5-chloro-1H-pyrrole-3,4-dicarbonitrile in a 74% yield. The compound was fully characterized. Full article

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Graphical abstract

7 pages, 1489 KiB

Open AccessCommunication

Tetramethyl 1,1′-(2-[{4,5-bis(Methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate)

by Serigne Abdou Khadir Fall, Sara Hajib, Oumaima Karai, Younas Aouine, Salaheddine Boukhssas, Hassane Faraj and Anouar Alami

Molbank 2021, 2021(1), M1186; https://doi.org/10.3390/M1186 - 31 Jan 2021

Cited by 1 | Viewed by 2185

Abstract

A new compound tetramethyl 1,1′-(2-[{4,5-bis(methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate) (3) was prepared in two steps starting from 2-((4-methylphenyl)sulfonamido)-2-((tosyloxy)methyl)propane-1,3-diylbis(4-methylbenzenesulfonate) (1), with an overall yield of 74%. The key step being the copper-free Huisgen cycloaddition between N [...] Read more.

A new compound tetramethyl 1,1′-(2-[{4,5-bis(methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate) (3) was prepared in two steps starting from 2-((4-methylphenyl)sulfonamido)-2-((tosyloxy)methyl)propane-1,3-diylbis(4-methylbenzenesulfonate) (1), with an overall yield of 74%. The key step being the copper-free Huisgen cycloaddition between N-(1,3-diazido-2-(azidomethyl)propan-2-yl)-4-methylbenzenesulfonamide (2) and commercially available dimethyl acetylenedicarboxylate. The chemical structure of compound 3 was determined by IR, 1D and 2D NMR experiments, and elemental analysis. Full article

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Graphical abstract

6 pages, 714 KiB

Open AccessShort Note

N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine

by Valentin Wydra, Stefan Gerstenecker, Dieter Schollmeyer, Stanislav Andreev, Teodor Dimitrov, Ricardo Augusto Massarico Serafim, Stefan Laufer and Matthias Gehringer

Molbank 2021, 2021(1), M1181; https://doi.org/10.3390/M1181 - 18 Jan 2021

Cited by 2 | Viewed by 3175

Abstract

Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald–Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (¹H, ¹³C, [...] Read more.

Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald–Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (¹H, ¹³C, HSQC, HMBC, COSY, DEPT90 and NOESY), high resolution mass spectrometry (ESI-TOF-HRMS) and infrared spectroscopy (ATR-IR) and its structure was confirmed by single crystal X-ray diffraction. The inhibitory potency of the title compound was evaluated for selected kinases harboring a rare cysteine in the hinge region (MPS1, MAPKAPK2 and p70S6Kβ/S6K2). Full article

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4 pages, 1891 KiB

Open AccessShort Note

(S)-1-(Ethoxycarbonyl)ethyl(2R,5S)-2,5-dimethyl-1,3-dioxolan-4-one-2-carboxylate

by R. Alan Aitken, Oliver E. Haslett and Alexandra M. Z. Slawin

Molbank 2021, 2021(1), M1178; https://doi.org/10.3390/M1178 - 02 Jan 2021

Cited by 1 | Viewed by 2025

Abstract

The title compound was obtained in low yield in the condensation of ethyl pyruvate and lactic acid. Its structure is determined by NMR methods and x-ray diffraction and the mechanism for formation of this 1:2 adduct from the initial 1:1 adduct is considered. [...] Read more.

The title compound was obtained in low yield in the condensation of ethyl pyruvate and lactic acid. Its structure is determined by NMR methods and x-ray diffraction and the mechanism for formation of this 1:2 adduct from the initial 1:1 adduct is considered. Full article

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2020

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4 pages, 370 KiB

Open AccessShort Note

Methyl (2E)-3-[3-Benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidin-1-yl]acrylate

by Alexandra S. Golubenkova, Nikita E. Golantsov and Leonid G. Voskressensky

Molbank 2021, 2021(1), M1176; https://doi.org/10.3390/M1176 - 30 Dec 2020

Viewed by 2071

Abstract

Compounds with propargylamine moiety are useful synthetic precursors of several important classes of nitrogen-containing heterocycles. The title compound, methyl (2E)-3-[3-benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidine-1-yl]acrylate, has been prepared by domino-reaction, employing easily available 1-benzyl-2-(1-naphthyl)-4,5-dihydro-1H-imidazole and methyl propiolate in a high 92% yield. The structure [...] Read more.

Compounds with propargylamine moiety are useful synthetic precursors of several important classes of nitrogen-containing heterocycles. The title compound, methyl (2E)-3-[3-benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidine-1-yl]acrylate, has been prepared by domino-reaction, employing easily available 1-benzyl-2-(1-naphthyl)-4,5-dihydro-1H-imidazole and methyl propiolate in a high 92% yield. The structure of title compound was determined using ¹H-NMR, ¹³C-NMR, UV, FT-IR and HRMS (High-Resolution Mass Spectrometry). Full article

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Scheme 1

4 pages, 1659 KiB

Open AccessShort Note

4,4′-(Pyrrolo[3,2-b]pyrrole-1,4-diyl)dianiline

by Lorenza Giordano, Rafael Ballesteros and Rafael Ballesteros-Garrido

Molbank 2020, 2020(4), M1169; https://doi.org/10.3390/M1169 - 23 Nov 2020

Cited by 2 | Viewed by 2140

Abstract

4,4′-(Pyrrolo[3,2-b]pyrrole-1,4-diyl)dianiline was synthesized in one step from benzene-1,4-diamine and ethylene glycol with Pd/Al₂O₃ and ZnO. The title compound was characterized by means of NMR techniques and HRMS mass spectrometry. Full article

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Scheme 1

7 pages, 484 KiB

Open AccessShort Note

6-Nitro-7-tosylquinazolin-4(3H)-one

by Thi Ngoc Nguyen, Thi Phuong Thuy Tran, Thi Hoang Mai Vu, Hoa Binh Nguyen, Nguyet Suong Huyen Dao, Van Giang Nguyen, Dinh Luyen Nguyen, Nguyen Trieu Trinh and Van Hai Nguyen

Molbank 2020, 2020(4), M1168; https://doi.org/10.3390/M1168 - 21 Nov 2020

Viewed by 2717

Abstract

Sulfones are important building blocks in the construction of biologically active molecules or functional materials. The sulfonyl functional group in sulfones is so versatile that it can act as either a nucleophile, an electrophile, or a radical in different organic reactions. Recently, quinazoline [...] Read more.

Sulfones are important building blocks in the construction of biologically active molecules or functional materials. The sulfonyl functional group in sulfones is so versatile that it can act as either a nucleophile, an electrophile, or a radical in different organic reactions. Recently, quinazoline sulfones have been used to build asymmetrical ether derivatives as inhibitors of signaling pathways governed by tyrosine kinases and the epidermal growth factor-receptor. In this paper, we report a facile synthesis of a novel quinazoline sulfone, 6-nitro-7-tosylquinazolin-4(3H)-one (III), using the modified protocol from 7-chloro-6-nitroquinazolin-4(3H)-one (I) and sodium p-toluenesulfinate (II). The structure of the title compound III was determined using mass-spectrometry, FT-IR, ¹H-NMR, ¹³C-NMR, DEPT, HSQC (Heteronuclear single quantum coherence), HMBC (Heteronuclear Multiple Bond Correlation Spectroscopy) spectroscopies, and PXRD analysis. Full article

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5 pages, 745 KiB

Open AccessShort Note

Ethyl (S)-2-Benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate

by Mario A. Leyva-Acuña, Francisco Delgado-Vargas, Gabriela López-Angulo and Julio Montes-Avila

Molbank 2020, 2020(4), M1166; https://doi.org/10.3390/M1166 - 13 Nov 2020

Viewed by 2278

Abstract

Pyrimidines are compounds with a wide range of biological activities, and the synthesis of pyrimidine derivatives—useful in chemical and medicinal applications—is important in medicinal chemistry. This work shows the synthesis under microwave irradiation of the novel compound ethyl (S)-2-benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate (3 [...] Read more.

Pyrimidines are compounds with a wide range of biological activities, and the synthesis of pyrimidine derivatives—useful in chemical and medicinal applications—is important in medicinal chemistry. This work shows the synthesis under microwave irradiation of the novel compound ethyl (S)-2-benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate (3) from (S)-N-α-benzoyl-l-arginine ethyl ester hydrochloride (1) and acetylacetone (2). Compound 3 was easily purified, obtained in moderate yield (70%), and fully characterized by UV-Vis, FTIR-ATR spectroscopy, ¹H-NMR, ¹³C-NMR, HRMS, and EI-MS. Full article

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Scheme 1

5 pages, 334 KiB

Open AccessShort Note

Sodium N-(3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate

by Egils Bisenieks, Janis Poikans, Aiva Plotniece, Eiva Bernotiene, Wei-Bor Tsai and Arkadij Sobolev

Molbank 2020, 2020(3), M1148; https://doi.org/10.3390/M1148 - 14 Jul 2020

Viewed by 2769

Abstract

The development of the methods for amide bond formation is important for various uses in the laboratory and industrial applications. The compounds combined in their structures 1,4-dihydroisonicotinic acids and amino acids linked with an amide bond can be considered as “privileged structures” due [...] Read more.

The development of the methods for amide bond formation is important for various uses in the laboratory and industrial applications. The compounds combined in their structures 1,4-dihydroisonicotinic acids and amino acids linked with an amide bond can be considered as “privileged structures” due to their broad range of biological activities. Herein, the formation of amide bond between 1,4-dihydroisonicotinic acid and l-methionine is reported. The coupling of l-methionine with pentafluorophenyl active ester of 1,4-dihydroisonicotinic acid appears to be a convenient and effective method for amide bond formation. Sodium N-(3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate has been successfully synthesized via a procedure where the key step is amide formation from 5-diethyl 4-(perfluorophenyl) 2,6-dimethyl-1,4-dihydropyridine-3,4,5-tricarboxylate and l-methionine. Sodium salt formation was performed to improve physicochemical properties, such as solubility of the l-methionine-derived 1,4-dihydroisonicotinamide. The obtained target compound was fully characterized by UV, IR, ¹H NMR, ¹³C NMR, MS, and microanalysis. Full article

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Graphical abstract

5 pages, 586 KiB

Open AccessFeature PaperShort Note

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

by Jack Bennett and Paul V. Murphy

Molbank 2020, 2020(2), M1140; https://doi.org/10.3390/M1140 - 03 Jun 2020

Viewed by 2354

Abstract

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) [...] Read more.

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by ¹H and ¹³C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring. Full article

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Scheme 1

6 pages, 887 KiB

Open AccessCommunication

Synthesis of (R) and (S)-3-Chloro-5-(2,4-dimethylpiperazin-1-yl)-4H-1,2,6-thiadiazin-4-ones

by Andreas S. Kalogirou, Christopher R. M. Asquith and Panayiotis A. Koutentis

Molbank 2020, 2020(2), M1139; https://doi.org/10.3390/M1139 - 01 Jun 2020

Cited by 2 | Viewed by 2414

Abstract

The reaction of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one with (R) and (S)-1,3-dimethylpiperazines (1 equiv), in THF, at ca. 20 °C gives (R) and (S)-3-chloro-5-(2,4-dimethylpiperazin-1-yl)-4H-1,2,6-thiadiazin-4-ones in 70% and 68% yields, respectively. The new compounds were fully characterized. Full article

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4 pages, 518 KiB

Open AccessShort Note

Methyl 2-(1-methyl-3-oxoisoindolin-1-yl)acetate

by Antonia Di Mola, Antonio Macchia, Laura Palombi and Antonio Massa

Molbank 2020, 2020(2), M1131; https://doi.org/10.3390/M1131 - 08 May 2020

Cited by 1 | Viewed by 2321

Abstract

In this work, we report a facile access to a 3,3-disubstituted isoindolinone by means of Krapcho decarboxylation reaction of the respective substituted dimethyl malonate derivative. Good isolated yields were obtained under mild reaction conditions. Full article

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Graphical abstract

5 pages, 1270 KiB

Open AccessFeature PaperShort Note

2-(Fluoromethyl)-4,7-dimethoxy-1-methyl-1H-benzimidazole

by Patrick Kielty, Pau Farràs, Dennis A. Smith and Fawaz Aldabbagh

Molbank 2020, 2020(2), M1129; https://doi.org/10.3390/M1129 - 01 May 2020

Cited by 1 | Viewed by 3044

Abstract

Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) substitutes the TEMPO free radical with fluorine on 4,7-dimethoxy-1-methyl-2-{[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]methyl}-1H-benzimidazole to give the title compound in a 77% yield. A mechanism is proposed for the formation of this novel methylene fluoride. Full article

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Graphical abstract

6 pages, 841 KiB

Open AccessCommunication

Synthesis of (R) and (S)-3-Chloro-5-(3-methylmorpholino)-4H-1,2,6-thiadiazin-4-ones

by Andreas S. Kalogirou, Christopher R. M. Asquith and Panayiotis A. Koutentis

Molbank 2020, 2020(2), M1128; https://doi.org/10.3390/M1128 - 27 Apr 2020

Cited by 1 | Viewed by 2295

Abstract

Reaction of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one with (R) and (S)-3-methylmorpholines (2 equiv), in THF, at ca. 20 °C gave (R) and (S)-3-chloro-5-(3-methylmorpholino)-4H-1,2,6-thiadiazin-4-ones in 95 and 97% yields, respectively. The new compounds were fully characterized. Full article

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Graphical abstract

7 pages, 2065 KiB

Open AccessShort Note

2,6-exo-8,12-exo-10-Butyl-13-oxa-3,5-dithia-10-azatetracyclo[5.5.1.0^2,6.0^8,12]tridecane-9,11-dione

by R. Alan Aitken, Fiona M. Fotherby and Alexandra M. Z. Slawin

Molbank 2020, 2020(2), M1123; https://doi.org/10.3390/M1123 - 02 Apr 2020

Cited by 2 | Viewed by 2630

Abstract

The title compound was obtained in low yield and spectroscopically characterised. Its X-ray structure was compared with the X-ray structures of other crystallographically-characterised 2-unsubstituted 1,3-dithiolanes. Full article

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Graphical abstract

5 pages, 727 KiB

Open AccessCommunication

6-Imino-1,2,3,4,8,9,10,11-octahydropyrido[1,2-a]pyrido[1′,2′:1,2]imidazo[4,5-f]benzimidazole-13-one: Synthesis and Cytotoxicity Evaluation

by Darren Conboy and Fawaz Aldabbagh

Molbank 2020, 2020(1), M1118; https://doi.org/10.3390/M1118 - 05 Mar 2020

Cited by 4 | Viewed by 2481

Abstract

The first report of an iminoquinone of imidazo[4,5-f]benzimidazole is described. The 2D-NOESY spectrum of 1,2,3,4,8,9,10,11-octahydropyrido[1,2-a]pyrido[1’,2’:1,2]imidazo[4,5-f]benzimidazol-6-amine was used to confirm the location of the imine moiety at the C-6 position of the title compound. Cytotoxicity data from the National Cancer Institute are included. Full article

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Figure 1

6 pages, 1515 KiB

Open AccessShort Note

Diethyl pyrrole-2,5-dicarboxylate

by R. Alan Aitken, Charles Bloomfield, Liam J. R. McGeachie and Alexandra M. Z. Slawin

Molbank 2020, 2020(1), M1117; https://doi.org/10.3390/M1117 - 17 Feb 2020

Cited by 1 | Viewed by 2346

Abstract

The title compound was obtained in moderate yield by a new and unexpected base-induced ring contraction from a 1,4-thiazine precursor. Its X-ray structure showing hydrogen bonded dimers was compared with those of other crystallographically characterised 2-acylpyrroles. Full article

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Figure 1

7 pages, 1201 KiB

Open AccessCommunication

1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one: Synthesis, Crystal Structure and Anti-Leukemic Activity

by Jean Guillon, Solène Savrimoutou, Sandra Rubio, Stéphane Moreau, Noël Pinaud, Mathieu Marchivie and Vanessa Desplat

Molbank 2020, 2020(1), M1113; https://doi.org/10.3390/M1113 - 29 Jan 2020

Cited by 7 | Viewed by 2506

Abstract

1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one has been successfully synthesized via a multi-step pathway starting from 2-nitroaniline. Structure characterization of this original pyrrolo[1,2-a]quinoxaline derivative was achieved by FT-IR, ¹H-NMR, ¹³C-NMR, X-Ray and HRMS spectral analysis. This title compound shows interesting cytotoxic potential [...] Read more.

1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one has been successfully synthesized via a multi-step pathway starting from 2-nitroaniline. Structure characterization of this original pyrrolo[1,2-a]quinoxaline derivative was achieved by FT-IR, ¹H-NMR, ¹³C-NMR, X-Ray and HRMS spectral analysis. This title compound shows interesting cytotoxic potential against several human leukemia cell lines (K562, HL60, and U937 cells). Full article

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2019

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9 pages, 2505 KiB

Open AccessCommunication

Novel One-Pot Synthesis of Methyl 4-Hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate: Synthetic and Crystallographic Studies

by Sergiy M. Kovalenko, Oleksandr G. Drushlyak, Irina S. Konovalova, Illia O. Mariutsa, Dmitry V. Kravchenko, Alexandre V. Ivachtchenko and Oleg D. Mitkin

Molbank 2019, 2019(4), M1085; https://doi.org/10.3390/M1085 - 14 Oct 2019

Cited by 2 | Viewed by 2535

Abstract

A new suitable method of synthesis of methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by condensation of methyl 2-isothiocyanatobenzoate and methyl malonate is described. The structure of the compound both and by-product methyl 2-(methoxycarbonothioylamino)benzoate was confirmed by means of elemental analysis, ¹H NMR, ¹³C NMR, LC/MS [...] Read more.

A new suitable method of synthesis of methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by condensation of methyl 2-isothiocyanatobenzoate and methyl malonate is described. The structure of the compound both and by-product methyl 2-(methoxycarbonothioylamino)benzoate was confirmed by means of elemental analysis, ¹H NMR, ¹³C NMR, LC/MS and single crystal X-ray diffraction. UV/Vis and IR spectra of compounds are described. The presence of a strong intramolecular hydrogen bond between the hydroxy group and the carbonyl oxygen atom of the ester group in methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate is shown. The crystal structure of product was stabilized through intermolecular hydrogen bonds. Full article

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8 pages, 1490 KiB

Open AccessShort Note

3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione

by Nadine Uwabagira and Balladka Kunhana Sarojini

Molbank 2019, 2019(4), M1083; https://doi.org/10.3390/M1083 - 03 Oct 2019

Cited by 1 | Viewed by 2150

Abstract

The compound 3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione has been designed, synthesized, and screened for its in vitro antibreast cancer activity, using human breast adenocarcinoma cell lines (MCF-7) and in vitro anti-inflammatory activity. By hemolysis assay, it showed that it has a nonhemolytic and nontoxic effect on human [...] Read more.

The compound 3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione has been designed, synthesized, and screened for its in vitro antibreast cancer activity, using human breast adenocarcinoma cell lines (MCF-7) and in vitro anti-inflammatory activity. By hemolysis assay, it showed that it has a nonhemolytic and nontoxic effect on human blood cell. The title compound 5, subjected to in vitro activities, showed that it is cytotoxic with an IC₅₀ of 42.30 µM and a good anti-inflammatory agent. The docking results against cyclin dependent kinase 2 (CDK2) (PDB ID: 3QQK) gave insights on its inhibitory activity. Full article

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5 pages, 1523 KiB

Open AccessShort Note

4-[(3,5-Dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole

by Sara Hajib, Anouar Alami, Hassane Faraj and Younas Aouine

Molbank 2019, 2019(3), M1074; https://doi.org/10.3390/M1074 - 19 Jul 2019

Cited by 2 | Viewed by 2666

Abstract

The compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole 2 was prepared in high yield, through nucleophilic substitution reaction of the O-tosyl oxazoline derivative 1, by heating in dimethyl sulfoxide (DMSO) and in presence of KOH as base. The structure of the synthesized compound was [...] Read more.

The compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole 2 was prepared in high yield, through nucleophilic substitution reaction of the O-tosyl oxazoline derivative 1, by heating in dimethyl sulfoxide (DMSO) and in presence of KOH as base. The structure of the synthesized compound was established on the basis of NMR spectroscopy (¹H, ¹³C), MS data and elemental analysis. Full article

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