SYNTHESIS AND ANTIVIRAL ACTIVITY OF 5'-DEOXYPYRAZOFURIN

In searching for derivatives of pyrazofurin that could display antiviral properties by means that do not require C-5' phosphorylation, 5'-deoxypyrazofurin (3) has been synthesized in six steps from methyl 5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside(4). Compound 3 was evaluated for antiviral activity against a large number of viruses including herpes-, pox-, myxo-, toga-, arena-, rhabdo-, picorna-, reo-, and retroviruses. Compound 3 proved active against respiratory syncytial virus (in HeLa cells), vaccinia virus (in embryonic skin-muscle fibroblast cells), vesicular stomatitis virus (in HeLa cells), and influenza A virus (in M adin-Darby canine kidney cells) at concentrations (ranging from 4 to 20 mug/mL) that were nontoxic to the confluent host cell cultures.