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 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.
D000241:Adenosine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000378:metabolism; D006860:Hydrogen Bonding; D011485:Protein Binding; D043684:Receptor, Adenosine A3; D018047:Receptors, Purinergic P1 / Q000378:metabolism*
D043684:Receptor, Adenosine A3; D018047:Receptors, Purinergic P1; C046756:5'-N-methylcarboxamideadenosine; D000241:Adenosine