title: Systematic synthesis and biological evaluation of alpha- and beta-D-xylofuranosyl nucleosides of the five naturally occurring bases in nucleic acids and related analogues.
abstract: The alpha- and beta-D-xylofuranosyl analogues of the naturally occurring nucleosides, as well as other D-xylofuranosyl derivatives, have been the subject of a systematic synthesis and examination of their biological, i.e. antiviral antimetabolic, and cytostatic properties. The beta anomers were prepared by glycosylation of purine and pyrimidine aglycons with peracylated 1-O-acetyl-alpha-D-xylofuranoses, followed by removal of the blocking groups. The alpha anomers were obtained by a multistep synthesis with use of 2-amino- or 2-mercapto-alpha-D-xylofuran[1',2':4,5]-2-oxazoline as starting material. The xylofuranosyl nucleosides were tested for their activity against a variety of RNA and DNA viruses and for inhibition of cell growth and macromolecule synthesis. Three compounds, 9-(beta-D-xylofuranosyl)adenine, 9-(beta-D-xylofuranosyl)guanine, and 1-(beta-D-xylofuranosyl)cytosine, showed marked biological activity.
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D002455:Cell Division / Q000187:drug effects; D007928:Lethal Dose 50; D051379:Mice; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D011817:Rabbits
chemical_list: D000998:Antiviral Agents; D009705:Nucleosides