Design and Synthesis of New 2-Aryl-4,5-Dihydro-thiazole Analogues: In Vitro Antibacterial Activities and Preliminary Mechanism of Action.
Design and Synthesis of New 2-Aryl-4,5-Dihydro-thiazole Analogues: In Vitro Antibacterial Activities and Preliminary Mechanism of Action.
复制标题
新型2-芳基-4,5-二氢噻唑类似物的设计与合成：体外抗菌活性及初步作用机制
DOI：
10.3390/molecules201119680
复制
发表时间：
2015-11-09
期刊：
影响因子：
--
通讯作者：
Zhang J
中科院分区：
文献类型：
--
作者：
Tan F;Shi B;Li J;Wu W;Zhang J
以半胱氨酸和取代苯甲腈为原料，采用无金属、无催化剂的新方法，设计合成了60个2-芳基-4，5-二氢噻唑，产率为%~89%。标题化合物的结构主要通过核磁共振波谱数据进行确证。抗菌活性测定表明，化合物(S)-2-(2′-hydroxyphenyl)-4-hydroxy-methyl-4，5-dihydrothiazole(7h)和(R)-2-(2′-hydroxyphenyl)-4-hydroxymethyl-4，5-dihydro-thiazole(7h‘)对青枯雷尔氏菌、紫丁香假单胞菌有明显的抑制作用。最低抑菌浓度(MIC)范围为3.91~31.24μg·m L−1。取代基的作用表明，除4，5-二氢噻唑类似物的2-芳基上引入2‘-羟基外，所有4，5-二氢噻唑类似物的2-芳基上都引入了2’-羟基，否则它们的抗菌活性均被抑制。扫描电子显微镜(SEM)和脂肪酸暴露实验结果表明，这些抗菌化合物对受试菌的脂肪酸合成有影响。
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.
登录
查看更多内容
影响因子：
1.1
作者：
Loughlin, WA;Knevitt, SA;Marshall, RL
通讯作者：
Marshall, RL
一种新型二氢恶唑抗生素 一种新型二氢恶唑抗生素
影响因子：
0.6
作者：
Zhang, Ji-Wen;Zhang, Wen-Juan;Wu, Wen-Jun
通讯作者：
Wu, Wen-Jun
影响因子：
1.7
作者：
Li, Long-Bo;Dan, Wen-Jia;Zhang, Ji-Wen
通讯作者：
Zhang, Ji-Wen
膜通透性和细胞形态调控钌(II)聚吡啶复合物的抗菌活性
影响因子：
2.7
作者：
Sun, Dongdong;Zhang, Weiwei;Wang, Weiyun
通讯作者：
Wang, Weiyun
DOI：
10.3390/molecules18032763
发表时间：
2013-03-01
期刊：
Molecules (Basel, Switzerland)
影响因子：
--
作者：
Zhang W;Wei S;Zhang J;Wu W
通讯作者：
Wu W