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 (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.
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. dsj5216@163.com.
Shijie
S
Du
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. luhz@cau.edu.cn.
Huizhe
H
Lu
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. yangdy@cau.edu.cn.
Dongyan
D
Yang
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. lihong129106@163.com.
Hong
H
Li
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. david9351@126.com.
Xilin
X
Gu
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. wanchuan2011@163.com.
Chuan
C
Wan
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. cauchangqing@gmail.com.
Changqing
C
Jia
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. woookooo@cau.edu.cn.
Mian
M
Wang
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. lixiuyun0115@163.com.
Xiuyun
X
Li
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. qinzhaohai@263.net.
Zhaohai
Z
Qin
D000577:Amides / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001549:Benzamides / Q000138:chemical synthesis* / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000494:pharmacology; D007191:Indazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D008958:Models, Molecular; D025282:Mycelium / Q000187:drug effects*; D009536:Niacinamide / Q000031:analogs & derivatives / Q000494:pharmacology; D011775:Pythium / Q000187:drug effects* / Q000254:growth & development; D021281:Quantitative Structure-Activity Relationship; D012232:Rhizoctonia / Q000187:drug effects* / Q000254:growth & development
D000577:Amides; D000935:Antifungal Agents; D001549:Benzamides; D001713:Biphenyl Compounds; D007191:Indazoles; C000604457:N-(2-(1H-indazol-1-yl)phenyl)-2-(trifluoromethyl)benzamide; D009536:Niacinamide; C550088:2-chloro-N-(4-chlorobiphenyl-2-yl)nicotinamide