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

作者：Tan, Fangfang; Shi, Baojun; Li, Jian; Wu, Wenjun; Zhang, Jiwen^*

来源：Molecules, 2015, 20(11): 20118-20130.

DOI：10.3390/molecules201119680

• synthesis
• 4,5-dihydrothiazole
• antibacterial activity
• antibacterial mechanism

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 1 - hydroxyphenyl)- 4- hydroxy- methyl- 4,5- dihydrothiazole ( 7h) and ( R)- 2-( 2 1 - hydroxyphenyl)- 4- hydroxymethyl- 4,5- dihydro- thiazole ( 7h 1) 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 mu g . 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 1 - 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.

• 出版日期2015-11
• 单位西北农林科技大学