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Special Issue "Research of Organic Chemicals for Biological Applications"

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: 31 October 2023 | Viewed by 8466

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Special Issue Editors

Dr. Claudia Sorbi

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Guest Editor

LiBraMedChem Lab, University of Modena and Reggio Emilia, Modena, Italy
Interests: medicinal chemistry; organic chemistry; synthesis of sigma and 5-HT1A/5-HT7 selective receptors ligands; DAT and HDAC6 inhibitors; NMR; HPLC-MS; FT-IR analyses

Dr. Pasquale Linciano

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Guest Editor

The Department of Drug Science, University of Pavia, Pavia, Italy
Interests: medicinal chemistry; characterization of chiral compounds; CADD, design and synthesis of sigma receptors ligands with neuroprotective activity; anticancer agents acting as proteasome inhibitors or RNA-Binding protein disruptors; antimicrobial resistance; antiparasitic drugs

Special Issue Information

Dear Colleagues,

Drugs are chemicals used for medicinal purposes. They interact with complex chemical systems of humans. For this reason, organic chemicals and biology are closely related and the role of chemistry in the discovery and manufacture of new drugs is crucial.

This Special Issue covers research in medicinal chemistry, organic synthesis and analytical chemistry, useful for the rational design, synthesis and characterization of small molecules endowed with biological activity, in particular of pharmaceutical relevance.
Contributions on the most interesting developments in the organic chemistry, medicinal chemistry and chemical biology areas are welcome. These should concern:

The rational design and structural optimization of hits and leads (i.e., computational, chemical, biophysical sciences), and the application of these technologies to the modern pharmaceutical research;
The support of organic chemistry to the identification of new molecular targets through the synthesis of small molecule modulators that could be modulators of characterized (structure-based drug design, SBDD), or non-characterized biological targets (ligand-based drug design, LBDD);
The development of advanced synthetic methodologies (such as organo-catalyzed, stereo-controlled, solvent-free, high pressure and microwave assisted synthetic procedures) and chemical technologies (such as flow chemistry, electrochemistry, photocatalysis), which directly affect the synthesis of new drug-like molecules or simply of new chemical entities. Particular attention will be paid to the development and application of environmentally sustainable synthetic techniques in view of the current global green transition;
The application of advanced spectroscopic and spectrometric techniques (NMR, LC-(HR)MS, UV, and FT-IR) useful to structurally characterize the synthesized new organic molecules, to study the ligand-receptor interactions, and to develop the new biologically active molecules that have been discovered.

Full papers, communications, reviews and mini-reviews are welcome in this Special Issue.

Dr. Claudia Sorbi
Dr. Pasquale Linciano
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

medicinal chemistry
organic chemistry
organic synthesis
biological targets
therapeutics
drug design
drug analysis
pharmaceutical analysis.

Published Papers (7 papers)

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Research

Open AccessArticle

Synthesis, Characterization, and Anticancer Activity of New N,N′-Diarylthiourea Derivative against Breast Cancer Cells

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Molecules 2023, 28(17), 6420; https://doi.org/10.3390/molecules28176420 - 03 Sep 2023

Viewed by 581

Abstract

The goal of the current study was to prepare two new homologous series of N,N′-diarylurea and N,N′-diarylthiourea derivatives to investigate the therapeutic effects of these derivatives on the methodologies of inhibition directed on human MCF-7 cancer cells. The molecular structures of the prepared derivatives were successfully revealed through elemental analyses, ¹H-NMR, ¹³C-NMR and FT-IR spectroscopy. The cytotoxic results showed that Diarylthiourea (compound 4) was the most effective in suppressing MCF-7 cell growth when compared to all other prepared derivatives, with the most effective IC₅₀ value (338.33 ± 1.52 µM) after an incubation period of 24 h and no cytotoxic effects on normal human lung cells (wi38 cells). Using the annexin V/PI and comet tests, respectively, treated MCF-7 cells with this IC₅₀ value of the Diarylthiourea 4 compound displayed a considerable increase in early and late apoptotic cells, as well as an intense comet nucleus in comparison to control cells. An arrest of the cell cycle in the S phase was observed via flow cytometry in MCF-7 cells treated with the Diarylthiourea 4 compound, suggesting the onset of apoptosis. Additionally, ELISA research showed that caspase-3 was upregulated in MCF-7 cells treated with compound 4 compared to control cells, suggesting that DNA damage induced by compound 4 may initiate an intrinsic apoptotic pathway and activate caspase-3. These results contributed to recognizing that the successfully prepared Diarylthiourea 4 compound inhibited the proliferation of MCF-7 cancer cells by arresting the S cell cycle and caspase-3 activation via an intrinsic apoptotic route. These results, however, need to be verified through in vivo studies utilizing an animal model. Full article

(This article belongs to the Special Issue Research of Organic Chemicals for Biological Applications)

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Open AccessArticle

Design and Synthesis of New Acyl Urea Analogs as Potential σ1R Ligands

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Molecules 2023, 28(5), 2319; https://doi.org/10.3390/molecules28052319 - 02 Mar 2023

Viewed by 1158

Abstract

In search of synthetically accessible open-ring analogs of PD144418 or 5-(1-propyl-1,2,5,6-tetrahydropyridin-3-yl)-3-(p-tolyl)isoxazole, a highly potent sigma-1 receptor (σ1R) ligand, we herein report the design and synthesis of sixteen arylated acyl urea derivatives. Design aspects included modeling the target compounds for drug-likeness, docking at σ1R crystal structure 5HK1, and contrasting the lower energy molecular conformers with that of the receptor-embedded PD144418—a molecule we opined that our compounds could mimic pharmacologically. Synthesis of our acyl urea target compounds was achieved in two facile steps which involved first generating the N-(phenoxycarbonyl) benzamide intermediate and then coupling it with the appropriate amines weakly to strongly nucleophilic amines. Two potential leads (compounds 10 and 12, with respective in vitro σ1R binding affinities of 2.18 and 9.54 μM) emerged from this series. These leads will undergo further structure optimization with the ultimate goal of developing novel σ1R ligands for testing in neurodegeneration models of Alzheimer’s disease (AD). Full article

(This article belongs to the Special Issue Research of Organic Chemicals for Biological Applications)

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Open AccessArticle

Synthesis and the In Vitro Evaluation of Antitumor Activity of Novel Thiobenzanilides

Maria João Álvaro-Martins

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Molecules 2023, 28(4), 1877; https://doi.org/10.3390/molecules28041877 - 16 Feb 2023

Viewed by 962

Abstract

Cancer is a generic term for a large group of diseases that are the second-leading cause of death worldwide, accounting for nearly 10 million deaths in 2020. Melanoma is a highly aggressive skin tumor with an increasing incidence and poor prognosis in the metastatic stage. Breast cancer still stands as one of the major cancer-associated deaths among women, and diagnosed cases are increasing year after year worldwide. Despite the recent therapeutic advances for this type of cancer, novel drugs and treatment strategies are still urgently needed. In this paper, the synthesis of 18 thiobenzanilide derivatives (17 of them new) is described, and their cytotoxic potential against melanoma cells (A375) and hormone-dependent breast cancer (MCF-7) cells is evaluated using the MTT assay. In the A375 cell line, most of the tested thiobenzanilides derivatives showed EC₅₀ values in the order of μM. Compound 17 was the most promising, with an EC₅₀ (24 h) of 11.8 μM. Compounds 8 and 9 are also interesting compounds that deserve to be further improved. The MCF-7 cell line, on the other hand, was seen to be less susceptible to these thiobenzanilides indicating that these compounds show different selectivity towards skin and breast cancer cells. Compound 15 showed the highest cytotoxic potential for MCF-7 cells, with an EC₅₀ (24 h) of 43 μM, a value within the range of the EC₅₀ value determined for tamoxifen (30.0 μM). ADME predictions confirm the potential of the best compounds. Overall, this work discloses a new set of thiobenzanilides that are worth being considered as new scaffolds for the further development of anticancer agents. Full article

(This article belongs to the Special Issue Research of Organic Chemicals for Biological Applications)

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Open AccessArticle

Cannabidiol as Self-Assembly Inducer for Anticancer Drug-Based Nanoparticles

Eleonora Colombo

Davide Andrea Coppini

Laura Polito

Umberto Ciriello

Giuseppe Paladino

Mariafrancesca Hyeraci

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Molecules 2023, 28(1), 112; https://doi.org/10.3390/molecules28010112 - 23 Dec 2022

Cited by 2 | Viewed by 1318

Abstract

Cannabidiol (CBD) is a biologically active compound present in the plants of the Cannabis family, used as anticonvulsant, anti-inflammatory, anti-anxiety, and more recently, anticancer drug. In this work, its use as a new self-assembly inducer in the formation of nanoparticles is validated. The target conjugates are characterized by the presence of different anticancer drugs (namely N-desacetyl thiocolchicine, podophyllotoxin, and paclitaxel) connected to CBD through a linker able to improve drug release. These nanoparticles are formed via solvent displacement method, resulting in monodisperse and stable structures having hydrodynamic diameters ranging from 160 to 400 nm. Their biological activity is evaluated on three human tumor cell lines (MSTO-211H, HT-29, and HepG2), obtaining GI₅₀ values in the low micromolar range. Further biological assays were carried out on MSTO-211H cells for the most effective NP 8B, confirming the involvement of paclitaxel in cytotoxicity and cell death mechanism Full article

(This article belongs to the Special Issue Research of Organic Chemicals for Biological Applications)

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Open AccessArticle

Synthesis and Antiproliferative Effect of Halogenated Coumarin Derivatives

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Molecules 2022, 27(24), 8897; https://doi.org/10.3390/molecules27248897 - 14 Dec 2022

Cited by 2 | Viewed by 1400

Abstract

A series of 6- and 6,8-halocoumarin derivatives have been investigated as potential antiproliferative compounds against a panel of tumor and normal cell lines. Cytotoxic effects were determined by the MTT method. To investigate the potential molecular mechanism involved in the cytotoxic effect, apoptosis assay, cell cycle analysis, reactive oxygen species (ROS), and reduced glutathione analysis were performed. Among the screened compounds, coumarins 6,8-dibromo-2-oxo-2H-chromene-3-carbonitrile 2h and 6,8-diiodo-2-oxo-2H-chromene-3-carbonitrile 2k exhibited the most antiproliferative effect in thyroid cancer-derived cells TPC-1. The apoptosis assay showed that both 2h and 2k induced apoptosis in TPC-1 thyroid cancer cells. According to these experiments, both coumarins induced a slight increase in TPC-1 cells in the G2/M phase and a decrease in the S phase. A significant increase in ROS levels was observed in TPC-1 treated with diiodocoumarin 2k, while the dibromocoumarin 2h induced a decrease in ROS in a dose and time-dependent manner. Full article

(This article belongs to the Special Issue Research of Organic Chemicals for Biological Applications)

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Open AccessArticle

Synthesis of Sulfonamides Incorporating Piperidinyl-Hydrazidoureido and Piperidinyl-Hydrazidothioureido Moieties and Their Carbonic Anhydrase I, II, IX and XII Inhibitory Activity

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Molecules 2022, 27(17), 5370; https://doi.org/10.3390/molecules27175370 - 23 Aug 2022

Cited by 2 | Viewed by 1120

Abstract

Here we report a small library of hydrazinocarbonyl-ureido and thioureido benzenesulfonamide derivatives, designed and synthesized as potent and selective human carbonic anhydrase inhibitors (hCAIs). The synthesized compounds were evaluated against isoforms hCA I, II, IX and XII using acetazolamide (AAZ) as standard inhibitor. Several urea and thiourea derivatives showed inhibitory activity at low nanomolar levels with selectivity against the cytosolic hCA II isoform, as well as the transmembrane, tumor-associated enzymes hCA IX and XII. The thiourea derivatives showed enhanced potency as compared to urea analogues. Additionally, eight compounds 5g, 5m, 5o, 5q, 6l, 6j, 6o and 6u were selected for docking analysis on isoform I, II, IX, XII to illustrate the potential interaction with the enzyme to better understand the activity against the different isoforms. Full article

(This article belongs to the Special Issue Research of Organic Chemicals for Biological Applications)

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Open AccessArticle

One-Step, Low-Cost, Operator-Friendly, and Scalable Procedure to Synthetize Highly Pure N-(4-ethoxyphenyl)-retinamide in Quantitative Yield without Purification Work-Up

Silvana Alfei

and

Guendalina Zuccari

Molecules 2022, 27(11), 3632; https://doi.org/10.3390/molecules27113632 - 06 Jun 2022

Viewed by 1235

Abstract

It is widely reported that N-(4-hydroxyphenyl)-retinamide or fenretinide (4-HPR), which is a synthetic amide of all-trans-retinoic acid (ATRA), inhibits in vitro several types of tumors, including cancer cell lines resistant to ATRA, at 1–10 µM concentrations. Additionally, studies in rats and mice have confirmed the potent anticancer effects of 4-HPR, without evidencing hemolytic toxicity, thus demonstrating its suitability for the development of a new chemo-preventive agent. To this end, the accurate determination of 4-HPR levels in tissues is essential for its pre-clinical training, and for the correct determination of 4-HPR and its metabolites by chromatography, N-(4-ethoxyphenyl)-retinamide (4-EPR) has been suggested as an indispensable internal standard. Unfortunately, only a consultable old patent reports the synthesis of 4-EPR, starting from dangerous and high-cost reagents and using long and tedious purification procedures. To the best of our knowledge, no article existed so far describing the specific synthesis of 4-EPR. Only two vendors worldwide supply 4-ERP, and its characterization was incomplete. Here, a scalable, operator-friendly, and one-step procedure to synthetize highly pure 4-EPR without purification work-up and in quantitative yield is reported. Additionally, a complete characterization of 4-EPR using all possible analytical techniques has been provided. Full article

(This article belongs to the Special Issue Research of Organic Chemicals for Biological Applications)

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