Synthesis and antiherpesviral activity of 5-C-substituted uracil nucleosides.
Reaction of 2'-deoxy-5-hydroxyuridine with some Wittig reagents gave 5-alkoxycarbonylmethyl-, 5-carbamoylmethyl-, 5-cyanomethyl-and 5-acetonyl-2'-deoxyuridines. The corresponding 1-beta-D-arabinofuranosyl derivatives were prepared from 1-beta-D-arabinofuranosyl-5-hydroxymethyluracil. The latter was also converted to 1-beta-D-arabinofuranosyl-5-vinyluracil via triphenylphosphonium salt, and then to 5-(2-halogenovinyl)derivatives. Some of these compounds showed marked antiherpesviral activity in vitro.
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D008722:Methods; D018139:Simplexvirus / Q000187:drug effects; D014529:Uridine / Q000031:analogs & derivatives* / Q000494:pharmacology
D000998:Antiviral Agents; D014529:Uridine