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Pharmaceuticals
Special Issues
Design, Synthesis, and Biological Evaluation of Heterocyclic Compounds
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Design, Synthesis, and Biological Evaluation of Heterocyclic Compounds

A special issue of Pharmaceuticals (ISSN 1424-8247). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (20 March 2024) | Viewed by 5281

Special Issue Editor

Dr. Abbas G. Shilabin

E-Mail Website
Guest Editor
Department of Chemistry, East Tennessee State University, Johnson City, TN 37614, USA
Interests: synthetic organic chemistry; natural products chemistry; heterocyclic compounds; drug discovery and development; evaluation of biologically active molecules; structure-activity relationship studies
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

We are excited to announce a Special Issue dedicated to the fascinating world of heterocyclic compounds and their pivotal role in medicinal chemistry and drug discovery. Heterocyclic compounds represent a vast and diverse family within organic chemistry, making them a cornerstone of research in the field. Characterized by their heterocyclic core structures, they have emerged as a vital class of therapeutics for addressing a wide range of diseases.

The exceptional structural diversity and extensive bioactivity associated with heterocyclic compounds have piqued the interest of researchers worldwide. This Special Issue aims to shed light on the design, synthesis, and evaluation of these biologically active molecules across a spectrum of functional scaffolds. We invite you to contribute your original research and review articles to this Special Issue, where we will delve into the synthetic methodologies employed, the biological and medicinal significance of the generated heterocyclic compounds, and the crucial aspects of their purification, characterization, and analysis.

Topics of interest include, but are not limited to:

  1. Innovative Synthetic Methods: Exploring novel approaches and strategies for the efficient synthesis of heterocyclic compounds, including the development of new reactions, catalysts, and green synthesis methods.
  2. Structure–Activity Relationship (SAR) Studies: Investigating the relationship between the chemical structure of heterocyclic compounds and their biological activity, providing insights that can guide drug design.
  3. Biological Significance: Highlighting the potential therapeutic applications of heterocyclic compounds in treating various diseases, such as cancer, infectious diseases, neurodegenerative disorders, and more.
  4. Purification and Characterization: Discussing techniques and methods for the purification and characterization of heterocyclic compounds, ensuring their quality and reproducibility.
  5. Analytical Approaches: Presenting innovative analytical techniques for the quantification, identification, and analysis of heterocyclic compounds in complex matrices.

Your contributions will contribute to the collective knowledge in this dynamic and evolving field.

Please feel free to contact us if you have any questions or need further information. We look forward to receiving your contributions.

Dr. Abbas G. Shilabin
Guest Editor

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. Pharmaceuticals is an international peer-reviewed open access monthly 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 2900 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

  • heterocyclic compounds
  • synthetic methodology
  • drug discovery
  • biologically active molecules
  • structure–activity relationship (SAR) studies

Published Papers (5 papers)

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Research

17 pages, 1359 KiB  
Article
NMI-SO2Cl2-Mediated Amide Bond Formation: Facile Synthesis of Some Dihydrotriazolopyrimidine Amide Derivatives as Potential Anti-Inflammatory and Anti-Tubercular Agents
by Aravinda Babu, Kenchaiah Sunil, Ayyiliath Meleveetil Sajith, Eeda Koti Reddy, Sougata Santra, Grigory V. Zyryanov, Talavara Venkatesh, Somashekara Bhadrachari and Muthipeedika Nibin Joy
Pharmaceuticals 2024, 17(5), 548; https://0-doi-org.brum.beds.ac.uk/10.3390/ph17050548 - 24 Apr 2024
Viewed by 348
Abstract
Facile access to some novel biologically relevant dihydrotriazolopyrimidine carboxylic acid-derived amide analogues using NMI/SO2Cl2, and aromatic and aliphatic primary and secondary amines, is reported herein. The role of N-methylimidazole (NMI) as the base and sulfuryl chloride (SO2 [...] Read more.
Facile access to some novel biologically relevant dihydrotriazolopyrimidine carboxylic acid-derived amide analogues using NMI/SO2Cl2, and aromatic and aliphatic primary and secondary amines, is reported herein. The role of N-methylimidazole (NMI) as the base and sulfuryl chloride (SO2Cl2) as the coupling reagent has been effectively realized in accessing these molecules in good to excellent yields. The feasibility of the developed protocol has also been extended to the gram-scale synthesis of N-benzylbenzamide in a 75% yield from benzoic acid and benzyl amine. The newly synthesized compounds were tested via in vitro anti-inflammatory and anti-tubercular activity studies. The compounds 6aa and 6be were found to be the most active anti-inflammatory agents, whereas 6cb and 6ch were found to exhibit promising anti-tubercular potency when compared to other synthesized molecules. The structure–activity relationship (SAR) studies revealed the importance of the presence of electron-donating functionalities in enhancing the anti-inflammatory potential of the newly synthesized molecules. However, the presence of electron-withdrawing substituents was found to be significant for improving their anti-tubercular potency. Full article
(This article belongs to the Special Issue Design, Synthesis, and Biological Evaluation of Heterocyclic Compounds)
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Scheme 1

17 pages, 2451 KiB  
Article
Design, Synthesis and Biological Assessment of N′-(2-Oxoindolin-3-ylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazides as Potential Anti-Proliferative Agents toward MCF-7 Breast Cancer
by Najla A. Alshaye, Mohamed K. Elgohary, Mahmoud S. Elkotamy and Hatem A. Abdel-Aziz
Pharmaceuticals 2024, 17(2), 216; https://0-doi-org.brum.beds.ac.uk/10.3390/ph17020216 - 07 Feb 2024
Viewed by 834
Abstract
Breast cancer is a serious threat to the health and lives of women. Two novel series of N′-(2-oxoindolin-3-ylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazides and 1-(aryl)-3-(6-methylimidazo[2,1-b]thiazol-5-yl)ureas were designed, synthesized and investigated for their anticancer efficacy against the MCF-7 breast cell line. Three compounds of [...] Read more.
Breast cancer is a serious threat to the health and lives of women. Two novel series of N′-(2-oxoindolin-3-ylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazides and 1-(aryl)-3-(6-methylimidazo[2,1-b]thiazol-5-yl)ureas were designed, synthesized and investigated for their anticancer efficacy against the MCF-7 breast cell line. Three compounds of the first series showed potent activity toward MCF-7 with IC50 in the range 8.38–11.67 µM, respectively, as compared to Sorafenib (IC50 = 7.55 µM). N′-(1-butyl-2-oxoindolin-3-ylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide inhibited VEGFR-2 with IC50 = 0.33 µM when compared with Sorafenib (IC50 = 0.09 µM). Furthermore, this compound was introduced to PCR assessment, where it increased Bax, caspase 8, caspase 9 and cytochrome C levels by 4.337-, 2.727-, 4.947- and 2.420-fold, respectively, while it decreased levels of Bcl-2, as the anti-apoptotic gene, by 0.359-fold when compared to the untreated control MCF-7. This compound was also arrested in the G2/M phase by 27.07%, compared with 11.31% for the control MCF-7. Furthermore, it induced early and late apoptosis in MCF-7. In addition, a molecular docking study in the VEGFR-2 active site was performed to assess the binding profile for the most active compounds. Moreover, ADME parameters of the targeted compounds were also evaluated. Full article
(This article belongs to the Special Issue Design, Synthesis, and Biological Evaluation of Heterocyclic Compounds)
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Graphical abstract

22 pages, 10170 KiB  
Article
Discovery of Pyrano[2,3-c]pyrazole Derivatives as Novel Potential Human Coronavirus Inhibitors: Design, Synthesis, In Silico, In Vitro, and ADME Studies
by Abdou K. Allayeh, Aliaa H. El-boghdady, Mohamed A. Said, Mahmoud G. A. Saleh, Mohammed T. Abdel-Aal and Mohamed G. Abouelenein
Pharmaceuticals 2024, 17(2), 198; https://0-doi-org.brum.beds.ac.uk/10.3390/ph17020198 - 02 Feb 2024
Cited by 2 | Viewed by 1072
Abstract
The SARS-CoV-2 pandemic at the end of 2019 had major worldwide health and economic consequences. Until effective vaccination approaches were created, the healthcare sectors endured a shortage of operative treatments that might prevent the infection’s spread. As a result, academia and the pharmaceutical [...] Read more.
The SARS-CoV-2 pandemic at the end of 2019 had major worldwide health and economic consequences. Until effective vaccination approaches were created, the healthcare sectors endured a shortage of operative treatments that might prevent the infection’s spread. As a result, academia and the pharmaceutical industry prioritized the development of SARS-CoV2 antiviral medication. Pyranopyrazoles have been shown to play a prominent function in pharmaceutical chemistry and drug sighting because of their significant bioactive properties. We provide herein a novel sequence of pyranopyrazoles and their annulated systems whose antiviral efficacy and cytotoxicity were explored versus human coronavirus 229E (HCoV-229E) Vero-E6 cell lines as a model for the Coronaviridae family. Fifteen synthetic congeners pointed out miscellaneous antiviral efficacies against HCoV-229E with variable inhibition degrees. Compound 18 showed a high selectivity index (SI = 12.6) that established spectacular inhibitory capacity against human coronavirus 229E. Compounds 6, 7, and 14 exposed moderate efficacies. Compounds 6, 7, 14, and 18 exhibited substantial antiviral action through the replication phase with reduction percentages extending from 53.6%, 60.7%, and 55% to 82.2%, correspondingly. Likewise, when assessed to the positive control tipranavir (88.6%), the inhibitory efficiency of compounds 6, 7, 14, and 18 versus the SARS-CoV2 Mpro provided high percentages of 80.4%, 73.1%, 81.4% and up to 84.5%, respectively. In silico studies were performed to investigate further the biological activity and the target compounds’ physical and chemical features, including molecular dynamic (MD) simulations, protein–ligand docking, ADME studies, and density functional theory (DFT) calculations. These inquiries demonstrated that this series of metabolically stable pyranopyrazoles and their annulated systems are effective human coronavirus inhibitors that inhibit the viral Mpro protein and may have emerged as a novel COVID-19 curative option. Full article
(This article belongs to the Special Issue Design, Synthesis, and Biological Evaluation of Heterocyclic Compounds)
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Figure 1

16 pages, 3024 KiB  
Article
Design, Synthesis, Molecular Modeling and Biological Evaluation of Novel Pyrazole Benzimidazolone Derivatives as Potent Antioxidants
by Mohamed Adardour, Marouane Ait Lahcen, Mehdi Oubahmane, Walid Ettahiri, Ismail Hdoufane, Hafida Bouamama, Mohammed M. Alanazi, Driss Cherqaoui, Mustapha Taleb, Elena Zaballos Garcia and Abdesselam Baouid
Pharmaceuticals 2023, 16(12), 1648; https://0-doi-org.brum.beds.ac.uk/10.3390/ph16121648 - 24 Nov 2023
Cited by 1 | Viewed by 1077
Abstract
In the present study, we used benzimidazolone as a starting material to efficiently synthesize several hybrid compounds of pyrazole benzimidazolone derivatives by the 1,3-dipolar cycloaddition reaction. These compounds were obtained in average yields and were characterized by NMR (1H and 13 [...] Read more.
In the present study, we used benzimidazolone as a starting material to efficiently synthesize several hybrid compounds of pyrazole benzimidazolone derivatives by the 1,3-dipolar cycloaddition reaction. These compounds were obtained in average yields and were characterized by NMR (1H and 13C) and HRMS analysis. The antioxidant activity of the synthesized compounds 5(a–c) and 6(a–c) was evaluated using in vitro reduction assays, including ferric reducing antioxidant power (FRAP) and total antioxidant capacity (TAC). The results indicated that products 5c, 6b, and 6c exhibit higher antioxidant activity compared to the reference compounds and showed a remarkable ability to effectively remove the radical at IC50 (14.00 ± 0.14, 12.47± 0.02, and 12.82 ± 0.10 µM, respectively) under the TAC assessment. Conversely, compound 6c showed excellent activity at IC50 (68.97 ± 0.26 µM) in the FRAP assay. We carried out molecular docking and dynamics simulations to investigate the binding mode and stability of 5c, 6b, and 6c in the active site of human Peroxiredoxin 5. An ADMET study was conducted to determine the drug properties of the synthesized compounds. Full article
(This article belongs to the Special Issue Design, Synthesis, and Biological Evaluation of Heterocyclic Compounds)
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29 pages, 5815 KiB  
Article
Synthesis of Pyrrolo[3,4-b]pyridin-5-ones via Ugi–Zhu Reaction and In Vitro–In Silico Studies against Breast Carcinoma
by Ivette Morales-Salazar, Carlos E. Garduño-Albino, Flora P. Montes-Enríquez, Dania A. Nava-Tapia, Napoleón Navarro-Tito, Leonardo David Herrera-Zúñiga, Eduardo González-Zamora and Alejandro Islas-Jácome
Pharmaceuticals 2023, 16(11), 1562; https://0-doi-org.brum.beds.ac.uk/10.3390/ph16111562 - 06 Nov 2023
Viewed by 1535
Abstract
An Ugi–Zhu three-component reaction (UZ-3CR) coupled in a one-pot manner to a cascade process (N-acylation/aza Diels–Alder cycloaddition/decarboxylation/dehydration) was performed to synthesize a series of pyrrolo[3,4-b]pyridin-5-ones in 20% to 92% overall yields using ytterbium triflate as a catalyst, toluene [...] Read more.
An Ugi–Zhu three-component reaction (UZ-3CR) coupled in a one-pot manner to a cascade process (N-acylation/aza Diels–Alder cycloaddition/decarboxylation/dehydration) was performed to synthesize a series of pyrrolo[3,4-b]pyridin-5-ones in 20% to 92% overall yields using ytterbium triflate as a catalyst, toluene as a solvent, and microwaves as a heat source. The synthesized molecules were evaluated in vitro against breast cancer cell lines MDA-MB-231 and MCF-7, finding that compound 1f, at a concentration of 6.25 μM, exhibited a potential cytotoxic effect. Then, to understand the interactions between synthesized compounds and the main proteins related to the cancer cell lines, docking studies were performed on the serine/threonine kinase 1 (AKT1) and Orexetine type 2 receptor (Ox2R), finding moderate to strong binding energies, which matched accurately with the in vitro results. Additionally, molecular dynamics were performed between proteins related to the studied cell lines and the three best ligands. Full article
(This article belongs to the Special Issue Design, Synthesis, and Biological Evaluation of Heterocyclic Compounds)
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