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Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands
- Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands
- Lim M.H.; Kim H.O.; Moon H.R.; Lee S.J.; Chun M.W.; Gao Z.-G.; Melman N.; Jacobson K.A.; Kim J.H.; Jeong L.S.
- Ewha Authors
- 이승진; 정낙신
- SCOPUS Author ID
- Issue Date
- Journal Title
- Bioorganic and Medicinal Chemistry Letters
- vol. 13, no. 5, pp. 817 - 820
- SCI; SCIE; SCOPUS
- 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. © 2003 Elsevier Science Ltd. All rights reserved.
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