Synthesis of Novel S(N)-β-D-Glucosides of 4-N-(Substituted-2-hydroxyphenyl)-imino-5-(4-methyl-1,2,3-thiadiazol-5-yl)-2H-1,2,4-triazole-3-thiones and Their Antibacterial Activities

被引：8

作者：

Feng Zhong-Nian ^{[1
]}

Lu Jun-Rui ^{[1
]}

Xin Chun-Wei ^{[1
]}

Li Jian-Fa ^{[1
]}

Bao Xiu-Rong ^{[1
]}

Zhang Tong-Tong ^{[1
]}

机构：

[1] Tianjin Univ Technol, Sch Chem & Chem Engn, Tianjin 300384, Peoples R China

来源：

CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE | 2013年 / 34卷 / 05期

关键词：

1,2,4-Triazole; Glucoside; Synthesis; Antibacterial; DERIVATIVES; INHIBITORS;

D O I：

10.7503/cjcu20120954

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Eight novel S(N)-beta-D-glucosides were synthesized by glycosylation of 4-N-(substituted-2-hydroxyphenyl)-imino-5-(4-methyl-1,2,3-thiadiazol-5-yl)-2H-1,2,4-triazole-3-thiones (3a-3d) with bromo-2,3,4,6-tetra-O-acetyl-alpha-D-glueopyranoside in acetone in the presence of potassium hydroxide. The structures of all compounds were confirmed by IR, H-1 NMR and C-13 NMR spectra. The preliminary bioassay showed that all target compounds possessed efficient antibacterial activities on Staphylococcus aureus, Monilia albican and Escherichia coli, which is close to or better than the controlled drugs(triclosan and fluconazole). Especially the compounds 2-N-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)-4-N-(3,5-dibromo-2-hydroxyphenyl)-imino-5-(4-methyl-1,2,3-thiadiazol-5-yl)-1,2,4-triazole-3-thione(4d) and 3-S-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl-thio)-4-N-(3,5-dibromo-2-hydroxyphenyl)-imino-5-(4-methyl-1,2,3-thiadiazol-5-yl)-4H-1,2,4-triazole(5d) have strong antibacterial activities in vitro.

引用

页码：1143 / 1150

页数：8

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