A convenient new synthesis, characterization and antibacterial activity of double headed acyclo-C-nucleosides from unprotected d-glucose

Abstract

Double headed acyclo-C-nucleosides, 1,4-bis(3-mercapto-1H-1,2,4-triazol-5-yl)butane-1,2,3,4-tetrol (6), 5,5′-(1,2,3,4-tetrahydroxybutane-1,4-diyl)bis(1,3,4-oxadiazole-2(3H)-thione) (7), and 1,4-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)butane-1,2,3,4-tetrol (8) have been synthesized from d-glucose (1) without protecting hydroxyl groups. Two steps synthesis leading to formation of 2,3,4,5-tetrahydroxyhexanedihydrazide (4) which is regarded as starting intermediates for the synthesis of 6,7 and 8. Synthetic intermediates and final products were appropriately characterized by IR, 1H NMR and 13C NMR. The products were tested in vitro against gram positive bacteria Staphylococcus aureus, Listeria inovanii and gram negative bacteria Klebsiella pneumoniae, Salmonella sp., Escherichia coli and compared with the known antibiotic: amoxicillin + clavulanic acid (AMC) and showed variable effects.