title: Design and Synthesis of New 2-Aryl-4,5-Dihydro-thiazole Analogues: In Vitro Antibacterial Activities and Preliminary Mechanism of Action.
abstract: 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.
authors.affiliation: College of Science, Northwest Agriculture and Forestry University, Yangling 712100, China. 15877653513@163.com.
authors.forename: Fangfang
authors.initials: F
authors.lastname: Tan
authors.affiliation: Institute of Pesticide Science, Northwest Agriculture and Forestry University, Yangling 712100, China. shibaojun@nwsuaf.edu.cn.
authors.forename: Baojun
authors.initials: B
authors.lastname: Shi
authors.affiliation: College of Science, Northwest Agriculture and Forestry University, Yangling 712100, China. lijian3773@163.com.
authors.forename: Jian
authors.initials: J
authors.lastname: Li
authors.affiliation: Institute of Pesticide Science, Northwest Agriculture and Forestry University, Yangling 712100, China. wuwenjun@nwsuaf.edu.cn.
authors.forename: Wenjun
authors.initials: W
authors.lastname: Wu
authors.affiliation: College of Science, Northwest Agriculture and Forestry University, Yangling 712100, China. nwzjw@nwsuaf.edu.cn.|Institute of Pesticide Science, Northwest Agriculture and Forestry University, Yangling 712100, China. nwzjw@nwsuaf.edu.cn.
authors.forename: Jiwen
authors.initials: J
authors.lastname: Zhang
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects / Q000648:ultrastructure; D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D013844:Thiazoles
keywords: 4,5-dihydrothiazole; antibacterial activity; antibacterial mechanism; synthesis