Synthesis of 3'-ureidoadenosine analogues and their binding affinity to the A3 adenosine receptor.
Novel 3'-ureidoadenosine analogues were synthesized from 1,2:5, 6-di-O-isopropylidene-D-glucose in order to lead to stronger hydrogen bonding at the A3 adenosine receptor than the corresponding 3'-aminoadenosine derivatives. However, all synthesized 3'-ureidoadenosine analogues have lost their binding affinities to the all subtypes of adenosine receptors, indicating that bulky 3'-urea moiety led to conformational distortion.
Chun
Moon Woo
MW
Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, Korea.
Lee
Hyouk Woo
HW
Kim
Ae Yil
AY
Kim
Myong Jung
MJ
Kim
Hea Ok
HO
Gao
Zhan-Guo
ZG
Jacobson
Kenneth A
KA
Jeong
Lak Shin
LS
D000241:Adenosine / Q000737:chemistry*; D001665:Binding Sites; D015195:Drug Design; D005947:Glucose / Q000737:chemistry; D006801:Humans; D006860:Hydrogen Bonding; D008956:Models, Chemical; D008967:Molecular Biology / Q000379:methods*; D008968:Molecular Conformation; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000737:chemistry; D011485:Protein Binding; D043684:Receptor, Adenosine A3 / Q000737:chemistry* / Q000378:metabolism; D014508:Urea / Q000737:chemistry
D009705:Nucleosides; D043684:Receptor, Adenosine A3; D014508:Urea; D005947:Glucose; D000241:Adenosine