Synthesis and Antibacterial Activities of Novel S-β-D-Glucosides of 1,2,4-Triazole

doi:10.6023/cjoc201410021

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (4): 858-864.DOI: 10.6023/cjoc201410021 Previous Articles Next Articles

ARTICLE

新型S-β-D-葡萄糖苷-1,2,4-三唑的合成及其抗菌活性研究

张瑞波, 卢俊瑞, 辛春伟, 刘金彪, 穆江蓓, 杨旭云, 王宏韫, 王美君, 张贺

天津理工大学化学化工学院天津 300384

收稿日期:2014-10-15 修回日期:2014-11-19 发布日期:2014-12-09
通讯作者: 卢俊瑞 E-mail:lujunrui@tjut.edu.cn
基金资助:
国家自然科学基金(Nos. 21176194, 21476174)资助项目.

Synthesis and Antibacterial Activities of Novel S-β-D-Glucosides of 1,2,4-Triazole

Zhang Ruibo, Lu Junrui, Xin Chunwei, Liu Jinbiao, Mu Jiangbei, Yang Xuyun, Wang Hongyun, Wang Meijun, Zhang He

School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384

Received:2014-10-15 Revised:2014-11-19 Published:2014-12-09
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21176194, 21476174).

1. Synthesis and Antibacterial Activities of Novel S-β-D-Glucosides of 1,2,4-Triazole.PDF(976KB)

Abstract

A series potassiums 3 were prepared by substituted benzoyl hydrazide 2 and CS₂ in potassium hydroxide. These compounds 3 were converted to 4-amino-5-substituted phenyl-3-ylsulfanyl-4H-1,2,4-triazols (4) by cyclization in hydrazine hydrate. Nine novel S-β-D-glucosides (5a～5i) were synthesized by glycosylation of 4 and bromo-2,3,4,6-tetra-O-acetyl- α-D-glucopyranoside in the presence of potassium hydroxide with acetone as solvent. The structures of all target compounds were confirmed by ¹H NMR, ¹³C NMR, IR and HRMS spectrum. The results of preliminary bioassay show that most of the tested compounds displayed variable inhibitory activity against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Monilia albican. Especially, compound 5g has strong antibacterial activity with minimum inhibitory concentration values of 8, 16, 64, 2 μg/mL against four tested strains respectively which are similar to or higher than those of the controlled drug fluconazole or triclosan. The interaction and binding free energy of the target compounds 5a～5i with FabI were studied by Autodock Vina.

Key words: 1,2,4-triazole, 2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl, systhesis, antibacterial activity, FabI

Cite this article

Zhang Ruibo, Lu Junrui, Xin Chunwei, Liu Jinbiao, Mu Jiangbei, Yang Xuyun, Wang Hongyun, Wang Meijun, Zhang He. Synthesis and Antibacterial Activities of Novel S-β-D-Glucosides of 1,2,4-Triazole[J]. Chin. J. Org. Chem., 2015, 35(4): 858-864.

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新型S-β-D-葡萄糖苷-1,2,4-三唑的合成及其抗菌活性研究

Synthesis and Antibacterial Activities of Novel S-β-D-Glucosides of 1,2,4-Triazole

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