Synthesis and Binding Affinity of Homologated Adenosine Analogues as A3 Adenosine Receptor Ligands

被引：2

作者：

Lee, Hyuk Woo ^{[1
,2
]}

Choi, Won Jun ^{[1
,2
,3
]}

Jacobson, Kenneth A. ^{[4
]}

Jeong, Lak Shin ^{[1
,2
]}

机构：

[1] Ewha Womans Univ, Dept Bioinspired Sci, Coll Pharm, Seoul 120750, South Korea

[2] Ewha Womans Univ, Med Chem Lab, Coll Pharm, Seoul 120750, South Korea

[3] Dongguk Univ, Coll Pharm, Kyonggi Do 410774, South Korea

[4] NIDDKD, Mol Recognit Sect, Bioorgan Chem Lab, NIH, Bethesda, MD 20892 USA

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2011年 / 32卷 / 05期

关键词：

Co-2(CO)(8)-catalyzed siloxymethylation; A(3) adenosine receptor; Homologation; PHARMACOLOGY; ANTAGONISTS; DERIVATIVES; SUBTYPES; AGONISTS; CELLS;

D O I：

10.5012/bkcs.2011.32.5.1620

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Homologated analogues 3a and 3b of potent and selective A(3) adenosine receptor ligands, IB-MECA and dimethyl-IB-MECA were synthesized from commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (4) via Co-2(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.

引用

页码：1620 / 1624

页数：5

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