Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands

Moo Hong Lim, Hea Ok Kim, Hyung Ryong Moon, Seung Jin Lee, Moon Woo Chun, Zhan Guo Gao, Neli Melman, Kenneth A. Jacobson, Joong Hyup Kim, Lak Shin Jeong

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

Several 3′-fluoro analogues, 1a, 1b, and 1c of selective and potent adenosine A3 receptor agonist, Cl-IB-MECA were synthesized from D-xylose via highly regioselective opening of lyxo-epoxides, 8a and 8b with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A3 adenosine receptor, the corresponding 3′-fluoro derivative showed remarkably decreased binding affinity, indicating that 3′-hydroxyl group acts as hydrogen bonding acceptor, not hydrogen bonding donor like fluorine atom in binding to the A3 adenosine receptor.

Original languageEnglish
Pages (from-to)817-820
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume13
Issue number5
DOIs
StatePublished - 10 Mar 2003

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