551929-65-8Relevant articles and documents
Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands
Lim, Moo Hong,Kim, Hea Ok,Moon, Hyung Ryong,Lee, Seung Jin,Chun, Moon Woo,Gao, Zhan-Guo,Melman, Neli,Jacobson, Kenneth A.,Kim, Joong Hyup,Jeong, Lak Shin
, p. 817 - 820 (2007/10/03)
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.