title: Synthesis of 3'-acetamidoadenosine derivatives as potential A3 adenosine receptor agonists.
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.
authors.affiliation: College of Pharmacy, Seoul National University, Seoul, Korea. mwchun@snu.ac.kr
authors.forename: Moon Woo
authors.initials: MW
authors.lastname: Chun
authors.forename: Sung Wook
authors.initials: SW
authors.lastname: Choi
authors.forename: Tae Kyung
authors.initials: TK
authors.lastname: Kang
authors.forename: Won Jun
authors.initials: WJ
authors.lastname: Choi
authors.forename: Hea Ok
authors.initials: HO
authors.lastname: Kim
authors.forename: Zhan-Guo
authors.initials: ZG
authors.lastname: Gao
authors.forename: Kenneth A
authors.initials: KA
authors.lastname: Jacobson
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D058909:Adenosine A3 Receptor Agonists; D001665:Binding Sites; D006801:Humans; D006860:Hydrogen Bonding; D043684:Receptor, Adenosine A3 / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D058909:Adenosine A3 Receptor Agonists; D043684:Receptor, Adenosine A3; D000241:Adenosine