title: Synthesis and Binding Affinity of Homologated Adenosine Analogues as A3Adenosine Receptor Ligands.
abstract: Homologated analogues3aand3bof potent and selective A3adenosine receptor ligands, IB-MECA and dimethyl-IB-MECA were synthesized from commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose (4)viaCo2(CO)8-catalyzed siloxymethylation as a key step. Unfortunately, homologated analogues3aand3bdid not show significant binding affinities at three subtypes of adenosine receptors, indicating that free rotation, resulting from homologation, induced unfavorable interactions in the binding site of the receptor maybe due to the presence of many conformations.
authors.affiliation: Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.
authors.forename: Hyuk Woo
authors.initials: HW
authors.lastname: Lee
authors.affiliation: Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea. ; College of Pharmacy, Dongguk University, Kyungki-do 410-774, Korea.
authors.forename: Won Jun
authors.initials: WJ
authors.lastname: Choi
authors.affiliation: Molecular Recognition Section, Laboratory of Bioorganic Chemistry, National Institute of Diabetic, Digestive Disease and Kidney Disease, National Institutes of Health, Bethesda MD 20892-0810, USA.
authors.forename: Kenneth A
authors.initials: KA
authors.lastname: Jacobson
authors.affiliation: Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
keywords: A3 adenosine receptor; Co2(CO)8-catalyzed siloxymethylation; Homologation