Synthesis of 2-alkynyl substituted 4′-thioadenosine derivatives and their binding affinities at the adenosine receptors

Cheng Wu Liang, Won Jun Choi, Lak Shin Jeong

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

On the basis of high binding affinity of 2-hexynyl-N 6- methyladenosine and N 6-substituted-4′-thioadenosine derivatives at the A3 adenosine receptor (AR), novel 2-alkynyl-substituted-N 6-methyl-4′-thioadenosine derivatives, combining the characteristics of two classes of nucleosides were designed and synthesized from D-gulonic γ-lactone via palladium-catalyzed cross coupling reaction as a key step. Among compounds tested, only compound 3b showed moderate binding affinity at the human A3 adenosine receptor without binding affinities at other subtypes.

Original languageEnglish
Pages (from-to)973-977
Number of pages5
JournalArchives of Pharmacal Research
Volume31
Issue number8
DOIs
StatePublished - Aug 2008

Keywords

  • 2-Alkynyl-substituted-N -methyl-4′-thioadenosine; A adenosine receptor
  • Binding affinity
  • Diazotization
  • Palladium-catalyzed cross coupling

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