Novel simple efficient synthetic approach toward 6-substituted-2H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-3-thiones and first synthesis and biological evaluation of N-and S-beta-D-glucosides of the[1,2,4]triazolo [3,4-b][1,3,4]thiadiazole ring system

Novel simple and efficient synthetic approach for the synthesis of 6-substituted-2H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-3-thiones is described. Glucosidation of these novel bases with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide followed by chromatographic separation gave the corresponding N-and S-ss-D-glucosides. The structure of these two regiosiomers was established chemically and spectroscopically. Antimicrobial screening of two selected regioisomeric compounds against Aspergillus fumigatus, Penicillium italicum, Syncephalastrum racemosum, Candida albicans, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, and Escherichia coli are compared.