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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 5
BKCSDE 32(5)
May 20, 2011 

 
Title
Synthesis and Binding Affinity of Homologated Adenosine Analogues as A3 Adenosine Receptor Ligands
Author
Hyuk Woo Lee, Won Jun Choi, Kenneth A. Jacobson, Lak Shin Jeong*,
Keywords
Co2(CO)8-catalyzed siloxymethylation, A3 adenosine receptor, Homologation
Abstract
Homologated analogues 3a and 3b of potent and selective A3 adenosine receptor ligands, IB-MECA and dimethyl-IB-MECA were synthesized from commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-Dribofuranose (4) via Co2(CO)8-catalyzed siloxymethylation as a key step. Unfortunately, homologated analogues 3a and 3b did 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.
Page
1620 - 1624
Full Text
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