Synthesis of 1-(4-thio-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide.
The synthesis of 1-(4-thio-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (3) is described. The acid-catalyzed fusion procedure with 3-cyano-1,2,4-triazole and 1,2,3,5-tetra-O-acetyl-4-thio-D-ribofuranose provided 3-cyano-1-(2,3,5-tri-O-acetyl-4-thio-beta-D-ribofuranosyl-1,2,4-triazole (2) which was converted with NH4OH to 3. In contrast to 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide (1), the 4'-thio nucleoside 3 did not exhibt significant antiviral activity in vitro.
D000998:Antiviral Agents / Q000138:chemical synthesis; D012254:Ribavirin / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D012263:Ribonucleosides / Q000138:chemical synthesis*
D000998:Antiviral Agents; D012263:Ribonucleosides; D012254:Ribavirin; C013300:1-(4-thio-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide