Synthesis and binding affinity of homologated adenosine analogues as A3 adenosine receptor ligands

Hyuk Woo Lee; Won Jun Choi; Kenneth A. Jacobson; Lak Shin Jeong

doi:10.5012/bkcs.2011.32.5.1620

Synthesis and binding affinity of homologated adenosine analogues as A3 adenosine receptor ligands

Hyuk Woo Lee
, Won Jun Choi
, Kenneth A. Jacobson
, Lak Shin Jeong

Department of Pharmacy

Ewha Womans University
National Institutes of Health

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

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.

Original language	English
Pages (from-to)	1620-1624
Number of pages	5
Journal	Bulletin of the Korean Chemical Society
Volume	32
Issue number	5
DOIs	https://doi.org/10.5012/bkcs.2011.32.5.1620
State	Published - 20 May 2011

Keywords

A3 adenosine receptor
Co2(CO)8-catalyzed siloxymethylation
Homologation

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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.",

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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 - https://www.scopus.com/pages/publications/79957519264

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DO - 10.5012/bkcs.2011.32.5.1620

M3 - Article

AN - SCOPUS:79957519264

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VL - 32

SP - 1620

EP - 1624

JO - Bulletin of the Korean Chemical Society

JF - Bulletin of the Korean Chemical Society

IS - 5

ER -

Synthesis and binding affinity of homologated adenosine analogues as A3 adenosine receptor ligands

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Keywords

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