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, 3 a–e, as anti-HIV agents were designed and synthesized stereoselectively from d-gulonic γ-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.
|Number of pages||7|
|Journal||Asian Journal of Organic Chemistry|
|State||Published - 1 Jun 2016|
- cellular kinases