Synthesis, delivery, and molecular docking of fused quinolines as inhibitor of Hepatitis A virus 3C proteinase

Abstract It is widely accepted that Hepatitis A virus (HAV) is responsible for liver failure and even death in older people and in people with other serious health issues; so, proposing new compounds with inhibitory activity can help to treated of these disease’s. In current study, a new class of qu...

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Autores principales:	Mehrnaz Rafiei Jorshari, Manouchehr Mamaghani, Parivash Jahanshahi
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2021
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/10b4b0d8e8cf4f0f8b0868bdd550fddf
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spelling	oai:doaj.org-article:10b4b0d8e8cf4f0f8b0868bdd550fddf2021-12-02T18:48:02ZSynthesis, delivery, and molecular docking of fused quinolines as inhibitor of Hepatitis A virus 3C proteinase10.1038/s41598-021-98529-02045-2322https://doaj.org/article/10b4b0d8e8cf4f0f8b0868bdd550fddf2021-09-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-98529-0https://doaj.org/toc/2045-2322Abstract It is widely accepted that Hepatitis A virus (HAV) is responsible for liver failure and even death in older people and in people with other serious health issues; so, proposing new compounds with inhibitory activity can help to treated of these disease’s. In current study, a new class of quinolines is proposed with inhibitor activity of the HAV proteinase. So, in the first step, fused quinoline derivatives has been synthesized in short reaction time (12.0 min) and high efficiency yields (94%) in presence of 1-carboxymethyl-2,3-dimethylimidazolium iodide ([cmdmim]I) ionic liquid catalyst using a new method. In the following, chemical reactivity and inhibitory activity of synthesized quinolines were evaluated in density functional theory (DFT) framework and molecular docking methodologies. High global softness (0.67 eV), low HOMOSWBNNT-LUMO4a gap (4.78 eV), and more negative adsorption energy (− 87.9 kJ mol−1) in these quinolines reveal that the 4a and 4b compounds have better delivery than other quinolines using SWBNNT as suitable carrier to target cells. Molecular docking shows that the best cavity of the HAV has − 134.2 kJ mol−1 interaction energy involving bonding and non-bonding interactions. In fact, these interactions are between fused quinolines with especial geometries and sidechain flexibility amino acids residues inside the best binding site of the HAV, as hydrogen bonding, steric, and electrostatic interactions. So, these interactions imply that proposed fused quinolines have good inhibitor activity for the HAV.Mehrnaz Rafiei JorshariManouchehr MamaghaniParivash JahanshahiNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-8 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Mehrnaz Rafiei Jorshari Manouchehr Mamaghani Parivash Jahanshahi Synthesis, delivery, and molecular docking of fused quinolines as inhibitor of Hepatitis A virus 3C proteinase
description	Abstract It is widely accepted that Hepatitis A virus (HAV) is responsible for liver failure and even death in older people and in people with other serious health issues; so, proposing new compounds with inhibitory activity can help to treated of these disease’s. In current study, a new class of quinolines is proposed with inhibitor activity of the HAV proteinase. So, in the first step, fused quinoline derivatives has been synthesized in short reaction time (12.0 min) and high efficiency yields (94%) in presence of 1-carboxymethyl-2,3-dimethylimidazolium iodide ([cmdmim]I) ionic liquid catalyst using a new method. In the following, chemical reactivity and inhibitory activity of synthesized quinolines were evaluated in density functional theory (DFT) framework and molecular docking methodologies. High global softness (0.67 eV), low HOMOSWBNNT-LUMO4a gap (4.78 eV), and more negative adsorption energy (− 87.9 kJ mol−1) in these quinolines reveal that the 4a and 4b compounds have better delivery than other quinolines using SWBNNT as suitable carrier to target cells. Molecular docking shows that the best cavity of the HAV has − 134.2 kJ mol−1 interaction energy involving bonding and non-bonding interactions. In fact, these interactions are between fused quinolines with especial geometries and sidechain flexibility amino acids residues inside the best binding site of the HAV, as hydrogen bonding, steric, and electrostatic interactions. So, these interactions imply that proposed fused quinolines have good inhibitor activity for the HAV.
format	article
author	Mehrnaz Rafiei Jorshari Manouchehr Mamaghani Parivash Jahanshahi
author_facet	Mehrnaz Rafiei Jorshari Manouchehr Mamaghani Parivash Jahanshahi
author_sort	Mehrnaz Rafiei Jorshari
title	Synthesis, delivery, and molecular docking of fused quinolines as inhibitor of Hepatitis A virus 3C proteinase
title_short	Synthesis, delivery, and molecular docking of fused quinolines as inhibitor of Hepatitis A virus 3C proteinase
title_full	Synthesis, delivery, and molecular docking of fused quinolines as inhibitor of Hepatitis A virus 3C proteinase
title_fullStr	Synthesis, delivery, and molecular docking of fused quinolines as inhibitor of Hepatitis A virus 3C proteinase
title_full_unstemmed	Synthesis, delivery, and molecular docking of fused quinolines as inhibitor of Hepatitis A virus 3C proteinase
title_sort	synthesis, delivery, and molecular docking of fused quinolines as inhibitor of hepatitis a virus 3c proteinase
publisher	Nature Portfolio
publishDate	2021
url	https://doaj.org/article/10b4b0d8e8cf4f0f8b0868bdd550fddf
work_keys_str_mv	AT mehrnazrafieijorshari synthesisdeliveryandmoleculardockingoffusedquinolinesasinhibitorofhepatitisavirus3cproteinase AT manouchehrmamaghani synthesisdeliveryandmoleculardockingoffusedquinolinesasinhibitorofhepatitisavirus3cproteinase AT parivashjahanshahi synthesisdeliveryandmoleculardockingoffusedquinolinesasinhibitorofhepatitisavirus3cproteinase
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Synthesis, delivery, and molecular docking of fused quinolines as inhibitor of Hepatitis A virus 3C proteinase

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