Synthesis and anti-DNA -virus activity of the 5'-monophosphate and the cyclic 3',5'-monophosphate of 9-(beta-D-xylofuranosyl) guanine.
9-(beta-TD-xylofuranosyl)guanine (xylo-G) was converted chemically to the 9-(beta-D-xylofuranosyl)guanine 5'-monophosphate (xylo-GMP) and 9-(beta-D-xylofuranosyl)guanine cyclic 3',5'-monophosphate (c-xylo-GMP). These compounds were tested against a variety of DNA viruses in tissue culture in parallel with 9-(beta-D-arabinofuranosyl)adenine (ara-A). This evaluation revealed that xylo-G, xylo-GMP, and c-xylo-GMP were all moderately active but less effective than ara-A. When the four compounds were administered intracerebrally as a treatment for herpes virus, type 1 induced encephalitis in mice, c-xylo-GMP exhibited superior activity to that shown by the other three. When administered intraperitoneally, c-xylo-GMP was found to have a therapeutic index of about 4, which is less than that for ara-A (approximately 30) in the same system.
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis*; D006152:Cyclic GMP / Q000031:analogs & derivatives; D003588:Cytopathogenic Effect, Viral / Q000187:drug effects; D004267:DNA Viruses / Q000187:drug effects*; D004671:Encephalitis, Arbovirus / Q000188:drug therapy; D006150:Guanine Nucleotides / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D006564:Herpesviridae / Q000187:drug effects; D006566:Herpesviridae Infections / Q000188:drug therapy; D051379:Mice; D009712:Nucleotides, Cyclic / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D014616:Vaccinia virus / Q000187:drug effects
D000998:Antiviral Agents; D006150:Guanine Nucleotides; D009712:Nucleotides, Cyclic; C013338:9-(beta-D-xylofuranosyl)guanine cyclic 3',5'-monophosphate; D006152:Cyclic GMP