Synthesis of N⁶- or 8-Substituted 9-(β-D-Arabinofuranosyl)-adenines and Their Antiviral Activities against Herpes Simplex and Vaccinia Viruses

Abstract

9-(β-D-Arabinofuranosyl) adenine (Ara-A) was synthesized from adenosine 5'-monophosphate in 30% yield via 8, 2'-O-cycloadenosine as an intermediate. Various 8-substitutedamino Ara-A derivatives were obtained by aminolysis of 8, 2'-O-cycloadenosine and N⁶-substituted Ara-A derivatives were also obtained by reaction of 6-chloro-9-(β-D-arabinofuranosyl) purine with amines. In vitro antiviral activities of the N⁶- or 8-substituted Ara-A were determined by the degree of cytopathic effect inhibition.