5′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral Study

Abstract

The arbocyclic nucleosides aristeromycin and neplanocin have been studied as a source for new antiviral agents. A convenient synthesis of C-5′-truncated 3-deaza-1′,6′-isoneplanocin, which combines the features of antiviral candidates 5′-noraristeromycin and 3-deaza-1′,6′-isoneplanocin is reported from (−)-cyclopentenone to give the two C-4′ epimers of 5′-nor-3-deaza isoneplanocin. Antiviral assays showed activity against the JC virus (EC50 = 1.12 µM for (4′R)-8; EC50 = 59.14 µM for (4′S)-7) and inactivity of both compounds against several DNA and RNA viruses. Both compounds lacked cytotoxicity.