Novel 1,2,4-triazoles as anti-enzymatic agents: Microwave versus conventional synthesis, characterization, docking and BSA binding studies

Novel 1,2,4-triazoles as anti-enzymatic agents: Microwave versus conventional synthesis, characterization, docking and BSA binding studies

In the drug development process, 1,2,4-triazoles have become widely acknowledged as an effective structural motif. Through both classical and microwave supported approaches, analogues based on 1,2,4-triazole were synthesized, and they have the potential to act as strong anti-enzymatic agents. Starti...

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Published in:Journal of Molecular Structure
Main Author: Akhtar Virk N.; Rehman A.U.; Shuaib A.; Iqbal J.; Rasool S.; Al-Mijalli S.H.; Abid M.A.; Nisa M.-U.; Ali Shah S.A.; Saadiq M.
Format: Article
Language:English
Published: Elsevier B.V. 2023
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85150880224&doi=10.1016%2fj.molstruc.2023.135070&partnerID=40&md5=06db9e0181e27585f4b8ac6b49b9f770
id 2-s2.0-85150880224
spelling 2-s2.0-85150880224
Akhtar Virk N.; Rehman A.U.; Shuaib A.; Iqbal J.; Rasool S.; Al-Mijalli S.H.; Abid M.A.; Nisa M.-U.; Ali Shah S.A.; Saadiq M.
Novel 1,2,4-triazoles as anti-enzymatic agents: Microwave versus conventional synthesis, characterization, docking and BSA binding studies
2023
Journal of Molecular Structure
1281

10.1016/j.molstruc.2023.135070
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85150880224&doi=10.1016%2fj.molstruc.2023.135070&partnerID=40&md5=06db9e0181e27585f4b8ac6b49b9f770
In the drug development process, 1,2,4-triazoles have become widely acknowledged as an effective structural motif. Through both classical and microwave supported approaches, analogues based on 1,2,4-triazole were synthesized, and they have the potential to act as strong anti-enzymatic agents. Starting from 4‑methoxy benzensulfonyl chloride (1), subsequent carboxylate (3), carbohydrazide (4), 1,2,4-triazole (5) and their hybrids,7a-j, were successfully synthesized in attractive yields. All the synthesized analogs were characterized by 1H NMR, 13CNMR and IR spectral data. The enzymes acetyl cholinesterase (AChE), butyryl cholinesterase (BChE), and lipoxygenase (LOX), which are in charge of a variety of problems in people's daily lives, were considered in the biological assessment. Compounds,7g(IC50 (µM)=3.15±0.13) and 7h(IC50 (µM)=3.48±0.11) were outstanding against AChE while compounds, 7g(IC50 (µM)=39.17±0.29) and 7j(IC50 (µM)=35.42±0.41)against BChE comparative to Eserine(IC50 (µM)=0.19±0.05, 0.62±0.08)used as a standard respectively against both enzymes respectively. Inhibition potential against LOX was found excellent by compounds 7a(IC50 (µM)=12.53±0.25) and 7j(IC50 (µM)=19.28±0.46) among all the tested compoundsrelative to Quercetin(IC50 (µM)=2.34±0.35) used as a standard. The molecular docking and BSA (bovine serum albumin) binding studies further supported the physiologically active anti-enzymatic behaviors of synthesized compounds and they could be the future anti-enzymatic drugs after further assessments. © 2023
Elsevier B.V.
222860
English
Article
author Akhtar Virk N.; Rehman A.U.; Shuaib A.; Iqbal J.; Rasool S.; Al-Mijalli S.H.; Abid M.A.; Nisa M.-U.; Ali Shah S.A.; Saadiq M.
spellingShingle Akhtar Virk N.; Rehman A.U.; Shuaib A.; Iqbal J.; Rasool S.; Al-Mijalli S.H.; Abid M.A.; Nisa M.-U.; Ali Shah S.A.; Saadiq M.
Novel 1,2,4-triazoles as anti-enzymatic agents: Microwave versus conventional synthesis, characterization, docking and BSA binding studies
author_facet Akhtar Virk N.; Rehman A.U.; Shuaib A.; Iqbal J.; Rasool S.; Al-Mijalli S.H.; Abid M.A.; Nisa M.-U.; Ali Shah S.A.; Saadiq M.
author_sort Akhtar Virk N.; Rehman A.U.; Shuaib A.; Iqbal J.; Rasool S.; Al-Mijalli S.H.; Abid M.A.; Nisa M.-U.; Ali Shah S.A.; Saadiq M.
title Novel 1,2,4-triazoles as anti-enzymatic agents: Microwave versus conventional synthesis, characterization, docking and BSA binding studies
title_short Novel 1,2,4-triazoles as anti-enzymatic agents: Microwave versus conventional synthesis, characterization, docking and BSA binding studies
title_full Novel 1,2,4-triazoles as anti-enzymatic agents: Microwave versus conventional synthesis, characterization, docking and BSA binding studies
title_fullStr Novel 1,2,4-triazoles as anti-enzymatic agents: Microwave versus conventional synthesis, characterization, docking and BSA binding studies
title_full_unstemmed Novel 1,2,4-triazoles as anti-enzymatic agents: Microwave versus conventional synthesis, characterization, docking and BSA binding studies
title_sort Novel 1,2,4-triazoles as anti-enzymatic agents: Microwave versus conventional synthesis, characterization, docking and BSA binding studies
publishDate 2023
container_title Journal of Molecular Structure
container_volume 1281
container_issue
doi_str_mv 10.1016/j.molstruc.2023.135070
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85150880224&doi=10.1016%2fj.molstruc.2023.135070&partnerID=40&md5=06db9e0181e27585f4b8ac6b49b9f770
description In the drug development process, 1,2,4-triazoles have become widely acknowledged as an effective structural motif. Through both classical and microwave supported approaches, analogues based on 1,2,4-triazole were synthesized, and they have the potential to act as strong anti-enzymatic agents. Starting from 4‑methoxy benzensulfonyl chloride (1), subsequent carboxylate (3), carbohydrazide (4), 1,2,4-triazole (5) and their hybrids,7a-j, were successfully synthesized in attractive yields. All the synthesized analogs were characterized by 1H NMR, 13CNMR and IR spectral data. The enzymes acetyl cholinesterase (AChE), butyryl cholinesterase (BChE), and lipoxygenase (LOX), which are in charge of a variety of problems in people's daily lives, were considered in the biological assessment. Compounds,7g(IC50 (µM)=3.15±0.13) and 7h(IC50 (µM)=3.48±0.11) were outstanding against AChE while compounds, 7g(IC50 (µM)=39.17±0.29) and 7j(IC50 (µM)=35.42±0.41)against BChE comparative to Eserine(IC50 (µM)=0.19±0.05, 0.62±0.08)used as a standard respectively against both enzymes respectively. Inhibition potential against LOX was found excellent by compounds 7a(IC50 (µM)=12.53±0.25) and 7j(IC50 (µM)=19.28±0.46) among all the tested compoundsrelative to Quercetin(IC50 (µM)=2.34±0.35) used as a standard. The molecular docking and BSA (bovine serum albumin) binding studies further supported the physiologically active anti-enzymatic behaviors of synthesized compounds and they could be the future anti-enzymatic drugs after further assessments. © 2023
publisher Elsevier B.V.
issn 222860
language English
format Article
accesstype
record_format scopus
collection Scopus
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