Design and Synthesis of New 2-Aryl-4,5-dihydro-thiazole Analogues: In Vitro Antibacterial Activities and Preliminary Mechanism of Action

Molecules

Fangfang Tan²  Baojun Shi¹  Jian Li²  Wenjun Wu¹  Jiwen Zhang² 

[1] Institute of Pesticide Science, Northwest Agriculture and Forestry University, Yangling 712100, China;College of Science, Northwest Agriculture and Forestry University, Yangling 712100, China;

关键词: synthesis;    4;    5-dihydrothiazole;    antibacterial activity;    antibacterial mechanism;   

DOI  :  10.3390/molecules201119680

来源: mdpi

【 摘 要 】

Sixty 2-aryl-4,5-dihydrothiazoles were designed and synthesized in yields ranging from 64% to 89% from cysteine and substituted-benzonitriles via a novel metal- and catalyst-free method. The structures of the title compounds were confirmed mainly by NMR spectral data analysis. Antibacterial activity assays showed that the compounds (S)-2-(2′-hydroxyphenyl)-4-hydroxy-methyl-4,5-dihydrothiazole (7h) and (R)-2-(2′-hydroxyphenyl)-4-hydroxymethyl-4,5-dihydro-thiazole (7h′) exhibited significant inhibition against Ralstonia solanacearum, Pseudomonas syringae pv. actinidiae, Bacillus subtilis and Bacillus cereus, with minimum inhibitory concentrations (MICs) ranging from 3.91 to 31.24 μg·mL⁻¹. The effect of substituents showed that not only electron-withdrawing groups, but also electron-donating groups could abolish the antibacterial activities unless a 2′-hydroxy group was introduced on the 2-aryl substituent of the 4,5-dihydrothiazole analogues. The results of scanning electron microscope (SEM) and fatty acid exposure experiments indicated that these antibacterial compounds influence fatty acid synthesis in the tested bacteria.

【 授权许可】

CC BY   
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