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

Shijie Du; Zaimin Tian; Dongyan Yang; Xiuyun Li; Hong Li; Changqing Jia; Chuanliang Che; Mian Wang; Zhaohai Qin

doi:10.3390/molecules20058395

Molecules (May 2015)

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

Shijie Du,
Zaimin Tian,
Dongyan Yang,
Xiuyun Li,
Hong Li,
Changqing Jia,
Chuanliang Che,
Mian Wang,
Zhaohai Qin

Affiliations

Shijie Du: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Zaimin Tian: College of Agricultural and Forestry Science and Technology, Hebei North University, Zhangjiakou 075131, Hebei, China
Dongyan Yang: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Xiuyun Li: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Hong Li: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Changqing Jia: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Chuanliang Che: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Mian Wang: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Zhaohai Qin: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China

DOI: https://doi.org/10.3390/molecules20058395
Journal volume & issue: Vol. 20, no. 5
pp. 8395 – 8408

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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