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Synthesis and bioactivity evaluation of penta-1,4-diene-3-one oxime ether derivatives

A series of penta-1,4-diene-3-one oxime ether derivatives were synthesized, and their antiviral and antifungal activities were evaluated. Bioactivity evaluations showed that most target compounds had significant antiviral effects against tobacco mosaic virus (TMV). Among them, (1E,3Z,4E)-1-(4-(benzy...

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Autores principales: Tang, Xu, Su, Shijun, Li, Qin, He, Jun, Chen, Mei, Chen, Yu, Wu, Jiaxiang, Jiang, Shichun, Xue, Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Pesticide Science Society of Japan 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7457954/
https://www.ncbi.nlm.nih.gov/pubmed/32874125
http://dx.doi.org/10.1584/jpestics.D19-041
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author Tang, Xu
Su, Shijun
Li, Qin
He, Jun
Chen, Mei
Chen, Yu
Wu, Jiaxiang
Jiang, Shichun
Xue, Wei
author_facet Tang, Xu
Su, Shijun
Li, Qin
He, Jun
Chen, Mei
Chen, Yu
Wu, Jiaxiang
Jiang, Shichun
Xue, Wei
author_sort Tang, Xu
collection PubMed
description A series of penta-1,4-diene-3-one oxime ether derivatives were synthesized, and their antiviral and antifungal activities were evaluated. Bioactivity evaluations showed that most target compounds had significant antiviral effects against tobacco mosaic virus (TMV). Among them, (1E,3Z,4E)-1-(4-(benzyloxy)phenyl)-5-(furan-2-yl)penta-1,4-dien-3-one O-(3-fluorobenzyl) oxime (5e) was found to have good curative activity against TMV, with an inhibition rate of 64.6%, which was better than that of ribavirin (45.2%). (1E,3Z,4E)-1-(4-(benzyloxy) phenyl)-5-(furan-2-yl)penta-1,4-dien-3-one O-((6-chloropyridin-3-yl)methyl) oxime (5d) had a remarkable protective effect against TMV, with an inhibitory rate of 66.9%, which was better than that of ribavirin (61.8%). The inhibitory rate of (1E,3Z,4E)-1-(2-(benzyloxy)phenyl)-5-(furan-2-yl)penta-1,4-dien-3-one O-(4-chlorobenzyl) oxime(5m) in inactivation activity against TMV was 87.0%, which was better than that of ribavirin (77.9%). Further molecular docking studies indicated that compound 5m shows strong binding affinities toward the coat protein of tobacco mosaic virus. This result indicates that penta-1,4-diene-3-one oxime ether derivatives can play a significant role in discovering new antiviral agents.
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spelling pubmed-74579542020-08-31 Synthesis and bioactivity evaluation of penta-1,4-diene-3-one oxime ether derivatives Tang, Xu Su, Shijun Li, Qin He, Jun Chen, Mei Chen, Yu Wu, Jiaxiang Jiang, Shichun Xue, Wei J Pestic Sci Original Article A series of penta-1,4-diene-3-one oxime ether derivatives were synthesized, and their antiviral and antifungal activities were evaluated. Bioactivity evaluations showed that most target compounds had significant antiviral effects against tobacco mosaic virus (TMV). Among them, (1E,3Z,4E)-1-(4-(benzyloxy)phenyl)-5-(furan-2-yl)penta-1,4-dien-3-one O-(3-fluorobenzyl) oxime (5e) was found to have good curative activity against TMV, with an inhibition rate of 64.6%, which was better than that of ribavirin (45.2%). (1E,3Z,4E)-1-(4-(benzyloxy) phenyl)-5-(furan-2-yl)penta-1,4-dien-3-one O-((6-chloropyridin-3-yl)methyl) oxime (5d) had a remarkable protective effect against TMV, with an inhibitory rate of 66.9%, which was better than that of ribavirin (61.8%). The inhibitory rate of (1E,3Z,4E)-1-(2-(benzyloxy)phenyl)-5-(furan-2-yl)penta-1,4-dien-3-one O-(4-chlorobenzyl) oxime(5m) in inactivation activity against TMV was 87.0%, which was better than that of ribavirin (77.9%). Further molecular docking studies indicated that compound 5m shows strong binding affinities toward the coat protein of tobacco mosaic virus. This result indicates that penta-1,4-diene-3-one oxime ether derivatives can play a significant role in discovering new antiviral agents. Pesticide Science Society of Japan 2019-11-20 /pmc/articles/PMC7457954/ /pubmed/32874125 http://dx.doi.org/10.1584/jpestics.D19-041 Text en © 2019 Pesticide Science Society of Japan https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) License.
spellingShingle Original Article
Tang, Xu
Su, Shijun
Li, Qin
He, Jun
Chen, Mei
Chen, Yu
Wu, Jiaxiang
Jiang, Shichun
Xue, Wei
Synthesis and bioactivity evaluation of penta-1,4-diene-3-one oxime ether derivatives
title Synthesis and bioactivity evaluation of penta-1,4-diene-3-one oxime ether derivatives
title_full Synthesis and bioactivity evaluation of penta-1,4-diene-3-one oxime ether derivatives
title_fullStr Synthesis and bioactivity evaluation of penta-1,4-diene-3-one oxime ether derivatives
title_full_unstemmed Synthesis and bioactivity evaluation of penta-1,4-diene-3-one oxime ether derivatives
title_short Synthesis and bioactivity evaluation of penta-1,4-diene-3-one oxime ether derivatives
title_sort synthesis and bioactivity evaluation of penta-1,4-diene-3-one oxime ether derivatives
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7457954/
https://www.ncbi.nlm.nih.gov/pubmed/32874125
http://dx.doi.org/10.1584/jpestics.D19-041
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