Lim, MH Kim, HO Moon, HR Lee, SJ Chun, MW Gao, ZG Melman, N Jacobson, KA Kim, JH Jeong, LS 2024-01-21T09:09:52Z 2024-01-21T09:09:52Z 2021-09-03 2003-03-10 0960-894X https://pubs.kist.re.kr/handle/201004/138742 Several 3'-fluoro analogues, la, 1b, and le of selective and potent adenosine A(3) receptor agonist, Cl-IB-MECA were synthesized from D-xylose via highly regioselective opening of lyxo-epoxides, 8a and 811 with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A(3) 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 A(3) adenosine receptor. (C) 2003 Elsevier Science Ltd. All rights reserved. English PERGAMON-ELSEVIER SCIENCE LTD RAT-BRAIN Design, synthesis and binding affinity of 3 '-fluoro analogues of Cl-IB-MECA as adenosine A(3) receptor ligands Article 10.1016/S0960-894X(03)00027-1 1 BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, v.13, no.5, pp.817 - 820 BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 13 5 817 820 scie scopus 000181563500009 2-s2.0-0037430454 Chemistry, Medicinal Chemistry, Organic Pharmacology & Pharmacy Chemistry Article RAT-BRAIN Cl-IB-MECA