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Molecules 2015, 20(11), 20118-20130; doi:10.3390/molecules201119680

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

1,†
,
2,†
,
1
,
2
and
1,2,*
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
Received: 9 September 2015 / Revised: 27 October 2015 / Accepted: 2 November 2015 / Published: 9 November 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [2153 KB, uploaded 9 November 2015]   |  

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
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Tan, F.; Shi, B.; Li, J.; Wu, W.; Zhang, J. Design and Synthesis of New 2-Aryl-4,5-Dihydro-thiazole Analogues: In Vitro Antibacterial Activities and Preliminary Mechanism of Action. Molecules 2015, 20, 20118-20130.

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