Synthesis of substituted-phenyl-1,2,4-triazol-3-thione analogues with modified D-glucopyranosyl residues and their antiproliferative activities

A series of D-glucopyranosyl-1,2,4-triazole-3-thione derivatives 1a-1d were synthesized by the reaction of 1,2,4-triazole-3-thione Schiff bases 5a-5d with 2,3,4,6-tetra-O-acetyl-sigma-D-glucopyranosyl bromide. We demonstrate the conversion of 2 to 5, without the necessity of purification of both oxadiazole and triazole intermediates to afford the compounds 5. Their structures were confirmed by standard studies of H-1 NMR, IR, MS and elemental analysis. Analogues 5 and 1 have shown cytotoxic activity against human MCF-7 and Bel-7402 malignant cell lines. Crown Copyright (C) 2009 Published by Elsevier Masson SAS. All rights reserved.