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

doi:10.7503/cjcu20120954

Chem. J. Chinese Universities ›› 2013, Vol. 34 ›› Issue (5): 1143.doi: 10.7503/cjcu20120954

• Organic Chemistry • Previous Articles Next Articles

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

FENG Zhong-Nian, LU Jun-Rui, XIN Chun-Wei, LI Jian-Fa, BAO Xiu-Rong, ZHANG Tong-Tong

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

Received:2012-10-22 Online:2013-05-10 Published:2013-05-10

Abstract

Abstract:

Eight novel S(N)-β-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-α-D-glucopyranoside in acetone in the presence of potassium hydroxide. The structures of all compounds were confirmed by IR, ¹H NMR and ¹³C 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-β-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-β-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.

Key words: 1,2,4-Triazole, Glucoside, Synthesis, Antibacterial

CLC Number:

O626.26

TrendMD:

FENG Zhong-Nian, LU Jun-Rui, XIN Chun-Wei, LI Jian-Fa, BAO Xiu-Rong, ZHANG Tong-Tong. 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[J]. Chem. J. Chinese Universities, 2013, 34(5): 1143.

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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

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