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Design, Synthesis, Antifungal Activities and SARs of ( R )‐2‐Aryl‐4,5‐dihydrothiazole‐4‐carboxylic Acid Derivatives
Author(s) -
Liu Jingbo,
Li Yuxin,
Chen Youwei,
Hua Xuewen,
Wan Yingying,
Wei Wei,
Song Haibin,
Yu Shujing,
Zhang Xiao,
Li Zhengming
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201500619
Subject(s) - aryl , carbendazim , bioassay , fungicide , antifungal , chemistry , carboxylic acid , stereochemistry , biology , botany , organic chemistry , microbiology and biotechnology , ecology , alkyl
Based on the structure of natural product 2‐aryl‐4,5‐dihydrothiazole‐4‐carboxylic acid, a series of novel ( R )‐2‐aryl‐4,5‐dihydrothiazole‐4‐carboxylic acid derivatives were designed and synthesized. Their structures were characterized by 1 H NMR, 13 C NMR and HRMS. The single crystal structure of compound 9b was determined by X‐ray diffraction analysis. The antifungal activities were evaluated for the first time. The bioassay results indicated that most compounds exhibited moderate to good antifungal activities. The antifungal activities of compound 13a (against Cercospora arachidicola Hori), 13d (against Alternaria solani ), and 16e (against Cercospora arachidicola Hori) were 61.9%, 67.3% and 61.9%, respectively, which are higher than those of the commercial fungicides chlorothalonil and carbendazim. Moreover, compound 13d exhibited excellent antifungal activities against 7 kinds of the fungi tested (66.7%, 77.3%, 63.0%, 87.9%, 70.0%, 70.0% and 80.0% at 50 µg?mL). Therefore, 13d can be used as a new lead structure for the development of antifungal agents.