Systematic synthesis and biological evaluation of .alpha.- and .beta.-D-xylofuranosyl nucleosides of the five naturally occurring bases in nucleic acids and related analogs

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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.