title: Design and synthesis of 3'-ureidoadenosine-5'-uronamides: effects of the 3'-ureido group on binding to the A3 adenosine receptor.
abstract: On the basis of high binding affinity at the A(3) adenosine receptor of 3'-aminoadenosine derivatives with hydrogen bonding donor ability, novel 3'-ureidoadenosine analogues were synthesized from 1,2:5,6-di-O-isopropylidene-d-glucose in order to lead to stronger hydrogen bonding than the corresponding 3'-aminoadenosine derivatives. However, the synthesized 3'-ureidoadenosine analogues were totally devoid of binding affinity, because 3'-urea moiety caused steric and electrostatic repulsions at the binding site of the A(3) adenosine receptor, leading to conformational distortion.
authors.affiliation: Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, South Korea. lakjeong@ewha.ac.kr
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
authors.forename: Myong Jung
authors.initials: MJ
authors.lastname: Kim
authors.forename: Hea Ok
authors.initials: HO
authors.lastname: Kim
authors.forename: Zhan-Guo
authors.initials: ZG
authors.lastname: Gao
authors.forename: Soo-Kyung
authors.initials: SK
authors.lastname: Kim
authors.forename: Kenneth A
authors.initials: KA
authors.lastname: Jacobson
authors.forename: Moon Woo
authors.initials: MW
authors.lastname: Chun
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D058909:Adenosine A3 Receptor Agonists; D001665:Binding Sites; D015195:Drug Design; D006860:Hydrogen Bonding; D043684:Receptor, Adenosine A3 / Q000378:metabolism*; D013329:Structure-Activity Relationship
chemical_list: D058909:Adenosine A3 Receptor Agonists; D043684:Receptor, Adenosine A3; D000241:Adenosine