title: Design, synthesis and binding affinity of 3'-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands.
abstract: Several 3'-fluoro analogues, 1a, 1b, and 1c 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 8b 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.
authors.affiliation: College of Pharmacy, Seoul National University, Seoul 151-742, South Korea.
authors.forename: Moo Hong
authors.initials: MH
authors.lastname: Lim
authors.forename: Hea Ok
authors.initials: HO
authors.lastname: Kim
authors.forename: Hyung Ryong
authors.initials: HR
authors.lastname: Moon
authors.forename: Seung Jin
authors.initials: SJ
authors.lastname: Lee
authors.forename: Moon Woo
authors.initials: MW
authors.lastname: Chun
authors.forename: Zhan-Guo
authors.initials: ZG
authors.lastname: Gao
authors.forename: Neli
authors.initials: N
authors.lastname: Melman
authors.forename: Kenneth A
authors.initials: KA
authors.lastname: Jacobson
authors.forename: Joong Hyup
authors.initials: JH
authors.lastname: Kim
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000378:metabolism*; D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D015195:Drug Design; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000378:metabolism*; D007700:Kinetics; D008024:Ligands; D011485:Protein Binding; D058906:Purinergic P1 Receptor Agonists; D011869:Radioligand Assay; D051381:Rats; D043684:Receptor, Adenosine A3; D018047:Receptors, Purinergic P1 / Q000378:metabolism*; D011994:Recombinant Proteins / Q000819:agonists / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D006845:Hydrocarbons, Fluorinated; D008024:Ligands; D058906:Purinergic P1 Receptor Agonists; D043684:Receptor, Adenosine A3; D018047:Receptors, Purinergic P1; D011994:Recombinant Proteins; D000241:Adenosine; C090034:2-chloro-N(6)-(3-iodobenzyl)adenosine-5'-N-methyluronamide