TY - JOUR
T1 - Synthesis and binding affinity of homologated adenosine analogues as A3 adenosine receptor ligands
AU - Lee, Hyuk Woo
AU - Choi, Won Jun
AU - Jacobson, Kenneth A.
AU - Jeong, Lak Shin
PY - 2011/5/20
Y1 - 2011/5/20
N2 - 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.
AB - 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.
KW - A3 adenosine receptor
KW - Co2(CO)8-catalyzed siloxymethylation
KW - Homologation
UR - http://www.scopus.com/inward/record.url?scp=79957519264&partnerID=8YFLogxK
U2 - 10.5012/bkcs.2011.32.5.1620
DO - 10.5012/bkcs.2011.32.5.1620
M3 - Article
AN - SCOPUS:79957519264
SN - 0253-2964
VL - 32
SP - 1620
EP - 1624
JO - Bulletin of the Korean Chemical Society
JF - Bulletin of the Korean Chemical Society
IS - 5
ER -