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

Shijie Du; Huizhe Lu; Dongyan Yang; Hong Li; Xilin Gu; Chuan Wan; Changqing Jia; Mian Wang; Xiuyun Li; Zhaohai Qin

doi:10.3390/molecules20034071

Molecules (Mar 2015)

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

Shijie Du,
Huizhe Lu,
Dongyan Yang,
Hong Li,
Xilin Gu,
Chuan Wan,
Changqing Jia,
Mian Wang,
Xiuyun Li,
Zhaohai Qin

Affiliations

Shijie Du: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Huizhe Lu: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Dongyan Yang: 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
Xilin Gu: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Chuan Wan: 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
Mian Wang: 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
Zhaohai Qin: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China

DOI: https://doi.org/10.3390/molecules20034071
Journal volume & issue: Vol. 20, no. 3
pp. 4071 – 4087

Abstract

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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 (EC50 = 16.75 µg/mL) and Rhizoctonia solani (EC50 = 19.19 µg/mL), compared to the reference compound boscalid with EC50 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.

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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