Synthesis and antiviral activity of certain 5'-monophosphates of 9-D-arabinofuranosyladenine and 9-D-arabinofuranosylhypoxanthine.
A number of 5'-phosphates of 9-D-arabinofuranosyladenine and 9-D-arabinofuranosylhypoxanthine were prepared and tested against a variety of DNA viruses in tissue culture. The syntheses of the antiviral agent 9-beta-D-arabinofuranosylhypoxanthine 5'-monophosphate (6) and a series of related nucleotides, 9-beta-D-arabinofuranosyladenine 5'-O-methylphosphate (3), 9-beta-D-arabinofuranosylhypoxanthine 5'-O-methylphosphate (7), 9-beta-D-arabinofuranosylhypaxanthine cyclic 3',5'-phosphate (13), and 9-alpha-D-arabinofuranosylhypoxanthine 5'-monophosphate (17), are described. The concepts underlying the development of these antiviral agents are discussed. Comparison of the anti-DNA viral activity is made with 9-beta-D-arabinofuranosyladenine (ara-A). Reproducible antiviral activity against three DNA viruses in vitro at nontoxic dosage levels is demonstrated by 3,6, and other related nucleotides.
D000227:Adenine Nucleotides / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002277:Carcinoma; D002460:Cell Line; D003588:Cytopathogenic Effect, Viral / Q000187:drug effects; D006564:Herpesviridae / Q000187:drug effects; D006801:Humans; D007042:Hypoxanthines / Q000138:chemical synthesis* / Q000494:pharmacology; D007668:Kidney; D009062:Mouth Neoplasms; D011684:Purine Nucleosides / Q000138:chemical synthesis*; D011685:Purine Nucleotides / Q000138:chemical synthesis* / Q000494:pharmacology; D011817:Rabbits; D014616:Vaccinia virus / Q000187:drug effects; D014740:Vidarabine / Q000138:chemical synthesis* / Q000494:pharmacology
D000227:Adenine Nucleotides; D000998:Antiviral Agents; D007042:Hypoxanthines; D011684:Purine Nucleosides; D011685:Purine Nucleotides; D014740:Vidarabine