期刊
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
卷 13, 期 5, 页码 817-820出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0960-894X(03)00027-1
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资金
- Intramural NIH HHS [Z01 DK031117-20] Funding Source: Medline
Several 3'-fluoro analogues, la, 1b, and le of selective and potent adenosine A(3) receptor agonist, Cl-IB-MECA were synthesized from D-xylose via highly regioselective opening of lyxo-epoxides, 8a and 811 with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A(3) 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 A(3) adenosine receptor. (C) 2003 Elsevier Science Ltd. All rights reserved.
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