Synthesis of 3′-acetamidoadenosine derivatives as potential A 3 adenosine receptor agonists

Moon Woo Chun, Sung Wook Choi, Tae Kyung Kang, Won Jun Choi, Hea Ok Kim, Zhan Guo Gao, Kenneth A. Jacobson, Lak Shin Jeong

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

On the basis of high binding affinity of 3′-aminoadenosine derivatives 2b at the human A3 adenosine receptor (AR), 3′- acetamidoadenosine derivatives 3a-e were synthesized from 1,2:5,6-di-O- isopropylidene-D-glucose via stereoselective hydroboration as a key step. Although all synthesized compounds were totally devoid of binding affinity at the human A3AR, our results revealed that 3′-position of adenosine can only be tolerated with small size of a hydrogen bonding donor like hydroxyl or amino group in the binding site of human A3AR.

Original languageEnglish
Pages (from-to)408-420
Number of pages13
JournalNucleosides, Nucleotides and Nucleic Acids
Volume27
Issue number4
DOIs
StatePublished - Apr 2008

Keywords

  • 3′-acetamidoadenosines
  • Human A adenosine receptor
  • Hydroboration-oxidation
  • Hydrogen bonding donor
  • Steric effects

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