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Synthesis, Antifungal Activity and QSAR of Some Novel Carboxylic Acid Amides

A series of novel aromatic carboxylic acid amides were synthesized and tested for their activities against six phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to good activity. Among them N-(2-(1H-indazol-1-yl)phenyl)-2-(trifluoromethyl)benzamide...

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Autores principales: Du, Shijie, Lu, Huizhe, Yang, Dongyan, Li, Hong, Gu, Xilin, Wan, Chuan, Jia, Changqing, Wang, Mian, Li, Xiuyun, Qin, Zhaohai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272411/
https://www.ncbi.nlm.nih.gov/pubmed/25749678
http://dx.doi.org/10.3390/molecules20034071
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author Du, Shijie
Lu, Huizhe
Yang, Dongyan
Li, Hong
Gu, Xilin
Wan, Chuan
Jia, Changqing
Wang, Mian
Li, Xiuyun
Qin, Zhaohai
author_facet Du, Shijie
Lu, Huizhe
Yang, Dongyan
Li, Hong
Gu, Xilin
Wan, Chuan
Jia, Changqing
Wang, Mian
Li, Xiuyun
Qin, Zhaohai
author_sort Du, Shijie
collection PubMed
description A series of novel aromatic carboxylic acid amides were synthesized and tested for their activities against six phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to good activity. Among them N-(2-(1H-indazol-1-yl)phenyl)-2-(trifluoromethyl)benzamide (3c) exhibited the highest antifungal activity against Pythium aphanidermatum (EC(50) = 16.75 µg/mL) and Rhizoctonia solani (EC(50) = 19.19 µg/mL), compared to the reference compound boscalid with EC(50) values of 10.68 and 14.47 µg/mL, respectively. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were employed to develop a three-dimensional quantitative structure-activity relationship model for the activity of the compounds. In the molecular docking, a fluorine atom and the carbonyl oxygen atom of 3c formed hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.
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spelling pubmed-62724112018-12-31 Synthesis, Antifungal Activity and QSAR of Some Novel Carboxylic Acid Amides Du, Shijie Lu, Huizhe Yang, Dongyan Li, Hong Gu, Xilin Wan, Chuan Jia, Changqing Wang, Mian Li, Xiuyun Qin, Zhaohai Molecules Article A series of novel aromatic carboxylic acid amides were synthesized and tested for their activities against six phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to good activity. Among them N-(2-(1H-indazol-1-yl)phenyl)-2-(trifluoromethyl)benzamide (3c) exhibited the highest antifungal activity against Pythium aphanidermatum (EC(50) = 16.75 µg/mL) and Rhizoctonia solani (EC(50) = 19.19 µg/mL), compared to the reference compound boscalid with EC(50) values of 10.68 and 14.47 µg/mL, respectively. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were employed to develop a three-dimensional quantitative structure-activity relationship model for the activity of the compounds. In the molecular docking, a fluorine atom and the carbonyl oxygen atom of 3c formed hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173. MDPI 2015-03-04 /pmc/articles/PMC6272411/ /pubmed/25749678 http://dx.doi.org/10.3390/molecules20034071 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Du, Shijie
Lu, Huizhe
Yang, Dongyan
Li, Hong
Gu, Xilin
Wan, Chuan
Jia, Changqing
Wang, Mian
Li, Xiuyun
Qin, Zhaohai
Synthesis, Antifungal Activity and QSAR of Some Novel Carboxylic Acid Amides
title Synthesis, Antifungal Activity and QSAR of Some Novel Carboxylic Acid Amides
title_full Synthesis, Antifungal Activity and QSAR of Some Novel Carboxylic Acid Amides
title_fullStr Synthesis, Antifungal Activity and QSAR of Some Novel Carboxylic Acid Amides
title_full_unstemmed Synthesis, Antifungal Activity and QSAR of Some Novel Carboxylic Acid Amides
title_short Synthesis, Antifungal Activity and QSAR of Some Novel Carboxylic Acid Amides
title_sort synthesis, antifungal activity and qsar of some novel carboxylic acid amides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272411/
https://www.ncbi.nlm.nih.gov/pubmed/25749678
http://dx.doi.org/10.3390/molecules20034071
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