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.
