Synthesis and Anti-HIV Activity of 5′-Homo-2′,3′-dideoxy-2′,3′-didehydro-4′-selenonucleosides (5′-Homo-4′-Se-d4 Ns)

Shuhao Qu, Gyudong Kim, Jinha Yu, Pramod K. Sahu, Yoojin Choi, Siddhi D. Naik, Lak Shin Jeong

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4 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)735-741
Number of pages7
JournalAsian Journal of Organic Chemistry
Volume5
Issue number6
DOIs
StatePublished - 1 Jun 2016

Keywords

  • 4′-Se-d4Ns
  • 4′-selenonucleosides
  • anti-HIV
  • cellular kinases
  • homologation

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