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Eco-Friendly Synthesis, Biological Evaluation, and In Silico Molecular Docking Approach of Some New Quinoline Derivatives as Potential Antioxidant and Antibacterial Agents

A new series of quinoline derivatives 5–12 were efficiently synthesized via one-pot multicomponent reaction (MCR) of resorcinol, aromatic aldehydes, β-ketoesters, and aliphatic/aromatic amines under solvent-free conditions. All products were obtained in excellent yields, pure at low-cost processing,...

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Autores principales: El-Saghier, Ahmed M., El-Naggar, Mohamed, Hussein, Abdel Haleem M., El-Adasy, Abu-Bakr A., Olish, M., Abdelmonsef, Aboubakr H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8222571/
https://www.ncbi.nlm.nih.gov/pubmed/34178944
http://dx.doi.org/10.3389/fchem.2021.679967
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author El-Saghier, Ahmed M.
El-Naggar, Mohamed
Hussein, Abdel Haleem M.
El-Adasy, Abu-Bakr A.
Olish, M.
Abdelmonsef, Aboubakr H.
author_facet El-Saghier, Ahmed M.
El-Naggar, Mohamed
Hussein, Abdel Haleem M.
El-Adasy, Abu-Bakr A.
Olish, M.
Abdelmonsef, Aboubakr H.
author_sort El-Saghier, Ahmed M.
collection PubMed
description A new series of quinoline derivatives 5–12 were efficiently synthesized via one-pot multicomponent reaction (MCR) of resorcinol, aromatic aldehydes, β-ketoesters, and aliphatic/aromatic amines under solvent-free conditions. All products were obtained in excellent yields, pure at low-cost processing, and short time. The structures of all compounds were characterized by means of spectral and elemental analyses. In addition, all the synthesized compounds 5–12 were in vitro screened for their antioxidant and antibacterial activity. Moreover, in silico molecular docking studies of the new quinoline derivatives with the target enzymes, human NAD (P)H dehydrogenase (quinone 1) and DNA gyrase, were achieved to endorse their binding affinities and to understand ligand–enzyme possible intermolecular interactions. Compound 9 displayed promising antioxidant and antibacterial activity, as well as it was found to have the highest negative binding energy of -9.1 and -9.3 kcal/mol for human NAD (P)H dehydrogenase (quinone 1) and DNA gyrase, respectively. Further, it complied with the Lipinski’s rule of five, Veber, and Ghose. Therefore, the quinoline analogue 9 could be promising chemical scaffold for the development of future drug candidates as antioxidant and antibacterial agents.
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spelling pubmed-82225712021-06-25 Eco-Friendly Synthesis, Biological Evaluation, and In Silico Molecular Docking Approach of Some New Quinoline Derivatives as Potential Antioxidant and Antibacterial Agents El-Saghier, Ahmed M. El-Naggar, Mohamed Hussein, Abdel Haleem M. El-Adasy, Abu-Bakr A. Olish, M. Abdelmonsef, Aboubakr H. Front Chem Chemistry A new series of quinoline derivatives 5–12 were efficiently synthesized via one-pot multicomponent reaction (MCR) of resorcinol, aromatic aldehydes, β-ketoesters, and aliphatic/aromatic amines under solvent-free conditions. All products were obtained in excellent yields, pure at low-cost processing, and short time. The structures of all compounds were characterized by means of spectral and elemental analyses. In addition, all the synthesized compounds 5–12 were in vitro screened for their antioxidant and antibacterial activity. Moreover, in silico molecular docking studies of the new quinoline derivatives with the target enzymes, human NAD (P)H dehydrogenase (quinone 1) and DNA gyrase, were achieved to endorse their binding affinities and to understand ligand–enzyme possible intermolecular interactions. Compound 9 displayed promising antioxidant and antibacterial activity, as well as it was found to have the highest negative binding energy of -9.1 and -9.3 kcal/mol for human NAD (P)H dehydrogenase (quinone 1) and DNA gyrase, respectively. Further, it complied with the Lipinski’s rule of five, Veber, and Ghose. Therefore, the quinoline analogue 9 could be promising chemical scaffold for the development of future drug candidates as antioxidant and antibacterial agents. Frontiers Media S.A. 2021-06-10 /pmc/articles/PMC8222571/ /pubmed/34178944 http://dx.doi.org/10.3389/fchem.2021.679967 Text en Copyright © 2021 El-Saghier, El-Naggar, Hussein, El-Adasy, Olish and Abdelmonsef. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
El-Saghier, Ahmed M.
El-Naggar, Mohamed
Hussein, Abdel Haleem M.
El-Adasy, Abu-Bakr A.
Olish, M.
Abdelmonsef, Aboubakr H.
Eco-Friendly Synthesis, Biological Evaluation, and In Silico Molecular Docking Approach of Some New Quinoline Derivatives as Potential Antioxidant and Antibacterial Agents
title Eco-Friendly Synthesis, Biological Evaluation, and In Silico Molecular Docking Approach of Some New Quinoline Derivatives as Potential Antioxidant and Antibacterial Agents
title_full Eco-Friendly Synthesis, Biological Evaluation, and In Silico Molecular Docking Approach of Some New Quinoline Derivatives as Potential Antioxidant and Antibacterial Agents
title_fullStr Eco-Friendly Synthesis, Biological Evaluation, and In Silico Molecular Docking Approach of Some New Quinoline Derivatives as Potential Antioxidant and Antibacterial Agents
title_full_unstemmed Eco-Friendly Synthesis, Biological Evaluation, and In Silico Molecular Docking Approach of Some New Quinoline Derivatives as Potential Antioxidant and Antibacterial Agents
title_short Eco-Friendly Synthesis, Biological Evaluation, and In Silico Molecular Docking Approach of Some New Quinoline Derivatives as Potential Antioxidant and Antibacterial Agents
title_sort eco-friendly synthesis, biological evaluation, and in silico molecular docking approach of some new quinoline derivatives as potential antioxidant and antibacterial agents
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8222571/
https://www.ncbi.nlm.nih.gov/pubmed/34178944
http://dx.doi.org/10.3389/fchem.2021.679967
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