Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents

Lak Shin Jeong, Yoo Na Choi, Dilip K. Tosh, Won Jun Choi, Hea Ok Kim, Jungwon Choi

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

On the basis of potent anti-HIV activity of 2',3'-dideoxynucleosides (ddNs), their bioisosteric analogues, 2',3'-dideoxy-4'-selenonucleosides (4'-seleno-ddNs) were first synthesized from a chiral template, d-glutamic acid using stereoselective ring-closure reaction of the dimesylate with Se2- and Pummerer type condensation of the selenoxide with nucleobases as key steps. X-ray crystallographic analysis indicated that 4'-seleno-ddNs adopted the same C2'-endo/C3'-exo (South) conformation as anti-HIV active ddNs, but did not show anti-HIV activity, indicating that RT seems to prefer the C2'-exo/C3'-endo (North) conformation on binding with their triphosphates.

Original languageEnglish
Pages (from-to)9891-9897
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number23
DOIs
StatePublished - 1 Dec 2008

Keywords

  • 2′,3′-Dideoxy-4′-selenonucleosides
  • 2′,3′-Dideoxycytidine
  • Anti-HIV agents
  • Pummerer type condensation
  • South conformation

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