Synthesis of 3′-fluoro analogue of Cl-IB-MECA as adenosine A3 receptor ligand

3′-Fluoro analogue 1 of selective and potent adenosine A3 receptor agonist, Cl-IB-MECA was synthesized from D-xylose via highly regioselective opening of lyxo-epoxide 4 with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A3 adenosine receptor, the corresponding 3′-fluoro...

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Bibliographic Details
Published in:Nucleic Acids Symposium Series 2003-09, Vol.3 (1), p.19-20
Main Authors: Chun, Moon Woo, Lim, Moo Hong, Moon, Hyung Ryong, Kim, Hea Ok, Jacobson, Kenneth A., Jeong, Lak Shin
Format: Article
Language:English
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Summary:3′-Fluoro analogue 1 of selective and potent adenosine A3 receptor agonist, Cl-IB-MECA was synthesized from D-xylose via highly regioselective opening of lyxo-epoxide 4 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 aftinity, indicating that 3′-hydroxyl group acts as hydrogen bonding donor, not hydrogen bonding acceptor like fluorine atom in binding to the A3 adenosine receptor.
ISSN:0261-3166
1746-8272
DOI:10.1093/nass/3.1.19