Synthesis of 3'-fluoro analogue of Cl-IB-MECA as adenosine A3 receptor ligand | Zendy

Moon Woo Chun | Zendy; Mikyoung Lim | Zendy; Hyung Ryong Moon | Zendy; H. O. Kim | Zendy; Kenneth A. Jacobson | Zendy; Lak Shin Jeong | Zendy

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

Author(s) -

Moon Woo Chun,

Mikyoung Lim,

Hyung Ryong Moon,

H. O. Kim,

Kenneth A. Jacobson,

Lak Shin Jeong

Publication year - 2003

Publication title -

nucleic acids symposium series

Language(s) - English

Resource type - Journals

eISSN - 1746-8272

pISSN - 0261-3166

DOI - 10.1093/nass/3.1.19

Subject(s) - chemistry , adenosine receptor , adenosine , agonist , hydrogen bond , ligand (biochemistry) , stereochemistry , fluoride , receptor , acceptor , medicinal chemistry , biochemistry , inorganic chemistry , molecule , organic chemistry , physics , condensed matter physics

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 affinity, indicating that 3'-hydroxyl group acts as hydrogen bonding donor, not hydrogen bonding acceptor like fluorine atom in binding to the A3 adenosine receptor.

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