Design and Synthesis of New 2-Aryl-4,5-Dihydro-thiazole Analogues: In Vitro Antibacterial Activities and Preliminary Mechanism of ActionReport as inadecuate




Design and Synthesis of New 2-Aryl-4,5-Dihydro-thiazole Analogues: In Vitro Antibacterial Activities and Preliminary Mechanism of Action - Download this document for free, or read online. Document in PDF available to download.

1

College of Science, Northwest Agriculture and Forestry University, Yangling 712100, China

2

Institute of Pesticide Science, Northwest Agriculture and Forestry University, Yangling 712100, China



These authors contributed equally to this work.





*

Author to whom correspondence should be addressed.



Academic Editor: Derek J. McPhee

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. View Full-Text

Keywords: synthesis; 4,5-dihydrothiazole; antibacterial activity; antibacterial mechanism synthesis; 4,5-dihydrothiazole; antibacterial activity; antibacterial mechanism





Author: Fangfang Tan 1,†, Baojun Shi 2,†, Jian Li 1, Wenjun Wu 2 and Jiwen Zhang 1,2,*

Source: http://mdpi.com/



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