Synthesis of 3′-acetamidoadenosine derivatives as potential a(3) adenosine receptor agonists.
Synthesis of 3\’-acetamidoadenosine derivatives as potential a(3) adenosine receptor agonists.
On the basis of high binding affinity of 3\’-aminoadenosine derivatives 2b at the human A(3) adenosine receptor (AR), 3\’-acetamidoadenosine derivatives 3a-e were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose via stereoselective hydroboration as a key step. Although all synthesized compounds were totally devoid of binding affinity at the human A(3)AR, our results revealed that 3\’-position of adenosine can only be tolerated with small size of a hydrogen bonding donor like hydroxyl or amino group in the binding site of human A(3)AR.
Chun MW, Choi SW, Kang TK, Choi WJ, Kim HO, Gao ZG, Jacobson KA, Jeong LS.
College of Pharmacy, Seoul National University, Seoul, Korea.