Potential antiviral agents. Stereospecific synthesis of purines and pyrimidines substituted with chiral acyclic chains by sugar-ring opening of α-L-arabinopyranosyl nucleosides

Abstract

3′,4′-Seco-nucleosides as well as their derivatives lacking C-3′, all retain the carbon framework and chirality of the β-D-ribofuranosyl moiety of the nucleosides occurring in nucleic acids, have been synthesized and their antiviral properties examined. Most of these chiral acyclic nucleosides were hitherto unknown and they were stereospecifically prepared by ring opening of α-L-arabinopyranosyl nucleosides by means of periodate oxidation followed by borohydride reduction. All the prepared compounds were tested for their activity against a variety of RNA and DNA viruses, but they did not show significant antiviral activity.