Synthesis and antiviral evaluation of 2′-deoxy-2′-C-trifluoromethyl β-<scp>d</scp>-ribonucleoside analogues bearing the five naturally occurring nucleic acid bases

Abstract

2'-Deoxy-2'-C-trifluoromethyl-beta-D-ribonucleoside derivatives bearing the five naturally occurring acid bases have been synthesized. All these derivatives were prepared by glycosylation reactions of purine and pyrimidine bases with a suitable peracylated 2-deoxy-2-C-trifluoromethyl sugar precursor to afford anomeric mixtures of protected nucleosides. After separation and deprotection, the resulting beta-nucleoside analogues were tested for their activity against HIV, HBV and several RNA viruses. However, none of these compounds showed significant antiviral activity nor cytotoxicity.