Synthesis and Anti-HIV Activity of 5'-Homo-2',3'-dideoxy-2',3'-dide hydro-4'-selenonucleosides (5'-Homo-4'-Se-d4Ns)

On the hypothesis that one carbon homologation of 4'-selenonucleosides might relieve the steric repulsion between cellular kinases and bulky selenium, 5'-homo-4'-Se-d4Ns, 3a-e, as anti-HIV agents were designed and synthesized stereoselectively from d-gulonic gamma -lactone, with the conversion of 2',3'-diol into the olefin as the key step. The anti-HIV activity of all synthesized compounds, 5'-homo-4'-Se-d4Ns, was toxicity-dependent, unlike normal 4'-Se-d4Ns, which were inactive against HIV-1. This result indicates that 5'-homo-4'-Se-d4Ns might be phosphorylated by cellular kinases as per the hypothesis. Se you there: Stereoselective synthesis of 5'-homo-2',3'-dideoxy-2',3'-dide hydro-4'-selenopyrimidine and purine nucleosides (4'-Se-d4Ns) 3a-e as anti-HIV agents was accomplished from d-gulonic gamma -lactone.