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KMID : 0617320030120010238
Journal of Pharmacetical Sceiences Ewha Womans University
2003 Volume.12 No. 1 p.238 ~ p.241
Design, Synthesis and Binding Affinity of 3¢¥-Fluoro Analogues of Cl-IB-MECA as Adenosine A©ý Receptor Ligands
Lim, Moo Hong
Kim, Hea Ok/Moon, Hyung Ryoung/Lee, Seung Jin/Chun, Moon Woo/Gao, Zhan-Guo/Melman, Neli
Abstract
Several 3¢¥-fluoro analogues, la, lb, and lc of selective and potent adenosine A©ý 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 CI-IB-MECA to the A©ý 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 fluorineatom in binding to the A©ý adenosine receptor.
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