Systematic synthesis and biological evaluation of alpha- and beta-D-lyxofuranosyl nucleosides of the five naturally occurring nucleic acid bases.
The alpha- and beta-D-lyxofuranosyl analogues of the naturally occurring nucleosides have been synthesized and their antiviral properties examined. The alpha anomers were prepared by glycosylation of purine and pyrimidine aglycons with tetra-O-acetyl-alpha-D-lyxofuranose, followed by removal of the blocking groups. The beta anomers were obtained by sequential oxidation and reduction of 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-beta-D-x ylofuranosyl nucleosides. The lyxofuranosyl nucleosides were tested for their activity against a variety of RNA and DNA viruses and for inhibition of cell growth. One compound, 9-alpha-D-lyxofuranosyladenine, showed activity against herpes simplex virus types 1 and 2 both in vitro and in vivo.
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006561:Herpes Simplex / Q000188:drug therapy; D051379:Mice; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
D000998:Antiviral Agents; D009705:Nucleosides