SYNTHESIS, STRUCTURE, AND ANTIPARASITIC ACTIVITY OF SULFAMOYL DERIVATIVES OF RIBAVIRIN

The triazole nucleoside derivatives l-(5'-O-sulfamoyl-β-D-ribofuranosyl)[1,2,4]triazole-3-carboxamide (2), l-(5'-O-sulfamoyl-i3-D-ribofuranosyl)[1,2,4]triazole-3-thiocarboxamide (3), and 1-(5'-O-sulfamoyl-β-D-ribofuranosyl)-[1,2,4]triazole-3-carbonitrile (4) were synthesized. Suitably protected triazole nucleosides were converted to their corresponding 5'-sulfamoyl derivatives, which on subsequent deprotection gave the desired compounds in good yields. The structures of compounds 2-4 were confirmed by X-ray crystallographic analysis. All three compounds showed significant antiparasitic activity in vitro, while 2 showed significant activity in vivo against Leishmania donovani and Trypanosoma brucei. © 1990, American Chemical Society. All rights reserved.