Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic Acid Amides

A series of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides were synthesized and their activities were tested against seven phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to excellent activities. Among them N-(2-(5-bromo-1...

Descripción completa

Detalles Bibliográficos
Autores principales: Du, Shijie, Tian, Zaimin, Yang, Dongyan, Li, Xiuyun, Li, Hong, Jia, Changqing, Che, Chuanliang, Wang, Mian, Qin, Zhaohai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272562/
https://www.ncbi.nlm.nih.gov/pubmed/26007171
http://dx.doi.org/10.3390/molecules20058395
_version_ 1783377186036645888
author Du, Shijie
Tian, Zaimin
Yang, Dongyan
Li, Xiuyun
Li, Hong
Jia, Changqing
Che, Chuanliang
Wang, Mian
Qin, Zhaohai
author_facet Du, Shijie
Tian, Zaimin
Yang, Dongyan
Li, Xiuyun
Li, Hong
Jia, Changqing
Che, Chuanliang
Wang, Mian
Qin, Zhaohai
author_sort Du, Shijie
collection PubMed
description A series of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides were synthesized and their activities were tested against seven phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to excellent activities. Among them N-(2-(5-bromo-1H-indazol-1-yl)phenyl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide (9m) exhibited higher antifungal activity against the seven phytopathogenic fungi than boscalid. Topomer CoMFA was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds. In molecular docking, the carbonyl oxygen atom of 9m could form hydrogen bonds towards the hydroxyl of TYR58 and TRP173 on SDH.
format Online
Article
Text
id pubmed-6272562
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62725622019-01-07 Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic Acid Amides Du, Shijie Tian, Zaimin Yang, Dongyan Li, Xiuyun Li, Hong Jia, Changqing Che, Chuanliang Wang, Mian Qin, Zhaohai Molecules Article A series of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides were synthesized and their activities were tested against seven phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to excellent activities. Among them N-(2-(5-bromo-1H-indazol-1-yl)phenyl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide (9m) exhibited higher antifungal activity against the seven phytopathogenic fungi than boscalid. Topomer CoMFA was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds. In molecular docking, the carbonyl oxygen atom of 9m could form hydrogen bonds towards the hydroxyl of TYR58 and TRP173 on SDH. MDPI 2015-05-08 /pmc/articles/PMC6272562/ /pubmed/26007171 http://dx.doi.org/10.3390/molecules20058395 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
Tian, Zaimin
Yang, Dongyan
Li, Xiuyun
Li, Hong
Jia, Changqing
Che, Chuanliang
Wang, Mian
Qin, Zhaohai
Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic Acid Amides
title Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic Acid Amides
title_full Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic Acid Amides
title_fullStr Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic Acid Amides
title_full_unstemmed Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic Acid Amides
title_short Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic Acid Amides
title_sort synthesis, antifungal activity and structure-activity relationships of novel 3-(difluoromethyl)-1-methyl-1h-pyrazole-4-carboxylic acid amides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272562/
https://www.ncbi.nlm.nih.gov/pubmed/26007171
http://dx.doi.org/10.3390/molecules20058395
work_keys_str_mv AT dushijie synthesisantifungalactivityandstructureactivityrelationshipsofnovel3difluoromethyl1methyl1hpyrazole4carboxylicacidamides
AT tianzaimin synthesisantifungalactivityandstructureactivityrelationshipsofnovel3difluoromethyl1methyl1hpyrazole4carboxylicacidamides
AT yangdongyan synthesisantifungalactivityandstructureactivityrelationshipsofnovel3difluoromethyl1methyl1hpyrazole4carboxylicacidamides
AT lixiuyun synthesisantifungalactivityandstructureactivityrelationshipsofnovel3difluoromethyl1methyl1hpyrazole4carboxylicacidamides
AT lihong synthesisantifungalactivityandstructureactivityrelationshipsofnovel3difluoromethyl1methyl1hpyrazole4carboxylicacidamides
AT jiachangqing synthesisantifungalactivityandstructureactivityrelationshipsofnovel3difluoromethyl1methyl1hpyrazole4carboxylicacidamides
AT chechuanliang synthesisantifungalactivityandstructureactivityrelationshipsofnovel3difluoromethyl1methyl1hpyrazole4carboxylicacidamides
AT wangmian synthesisantifungalactivityandstructureactivityrelationshipsofnovel3difluoromethyl1methyl1hpyrazole4carboxylicacidamides
AT qinzhaohai synthesisantifungalactivityandstructureactivityrelationshipsofnovel3difluoromethyl1methyl1hpyrazole4carboxylicacidamides

Ejemplares similares