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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...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Pesticide Science Society of Japan
2019
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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. |
format | Online Article Text |
id | pubmed-7457954 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Pesticide Science Society of Japan |
record_format | MEDLINE/PubMed |
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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