DSpace at EWHA: Synthesis of 3′-acetamidoadenosine derivatives as potential A 3 adenosine receptor agonists

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Synthesis of 3′-acetamidoadenosine derivatives as potential A 3 adenosine receptor agonists

Title: Synthesis of 3′-acetamidoadenosine derivatives as potential A 3 adenosine receptor agonists

Authors: Chun M.W.; Choi S.W.; Kang T.K.; Choi W.J.; Kim H.O.; Gao Z.-G.; Jacobson K.A.; Jeong L.S.

Abstract: On the basis of high binding affinity of 3′-aminoadenosine derivatives 2b at the human A3 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 A3AR, 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 A3AR. Copyright © Taylor & Francis Group, LLC.