Synthesis of novel pyrimidine thioglycosides as structural analogs of favipiravir (avigan) and their antibird flu virus activity.

Novel class of amino pyrimidine thioglycoside derivatives were designed from sodium 2-cyano-3-(arylamino)prop-1-ene-1,1-bis(thiolate) and guanidine hydrochloride to afford the corresponding sodium 2,6-diamino-5-aryl-1,2-dihydropyrimidine-4-thiolate , which in coupling with peracylated -D-gluco- and galactopyranosyl bromides in DMF gave the corresponding pyrimidine thioglycosides . Acidification of 2,6-diamino-5-aryl-1,2-dihydropyrimidine-4-thiolate salts with hydrochloric acid formed the corresponding pyrimidine-4-thioles . The latter were stirred with peracetylated halo sugars α-D-gluco- and galacto-pyranosyl bromides in sodium hydride and DMF to yield the pyrimidine thioglycosides . Deacetylation of the pyrimidine thioglycosides gave the corresponding free pyrimidine thioglycosides . The compounds were characterized by C NMR, H NMR, and IR. The pyrimidine thioglycosides and free pyrimidine thioglycosides were tested against H5N1 virus strain and exhibited high to moderate activity.