Synthesis and binding affinity of homologated adenosine analogues as A3 adenosine receptor ligands

Hyuk Woo Lee, Won Jun Choi, Kenneth A. Jacobson, Lak Shin Jeong

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Homologated analogues 3a and 3b of potent and selective A3 adenosine receptor ligands, IB-MECA and dimethyl-IB-MECA were synthesized from commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-Dribofuranose (4) via Co2(CO)8-catalyzed siloxymethylation as a key step. Unfortunately, homologated analogues 3a and 3b did not show significant binding affinities at three subtypes of adenosine receptors, indicating that free rotation, resulting from homologation, induced unfavorable interactions in the binding site of the receptor maybe due to the presence of many conformations.

Original languageEnglish
Pages (from-to)1620-1624
Number of pages5
JournalBulletin of the Korean Chemical Society
Volume32
Issue number5
DOIs
StatePublished - 20 May 2011

Keywords

  • A3 adenosine receptor
  • Co2(CO)8-catalyzed siloxymethylation
  • Homologation

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