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Structure-activity relationships of 2-chloro-N-6-substituted-4 '-thioadenosine-5 '-N,N-dialkyluronamides as human A(3) adenosine receptor antagonists
- Authors
- Jeong, Lak Shin; Lee, Hyuk Woo; Kim, Hea Ok; Tosh, Dilip K.; Pal, Shantanu; Choi, Won Jun; Gao, Zhan-Guo; Patel, Amit R.; Williams, Wanda; Jacobson, Kenneth A.; Kim, Hee-Doo
- Issue Date
- 1-Mar-2008
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Keywords
- 4 '-thionucleoside; A(3) adenosine receptor antagonist; conformational change; radioligand binding
- Citation
- BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, v.18, no.5, pp 1612 - 1616
- Pages
- 5
- Journal Title
- BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
- Volume
- 18
- Number
- 5
- Start Page
- 1612
- End Page
- 1616
- ISSN
- 0960-894X
1464-3405
- Abstract
- On the basis of potent and selective A(3) adenosine receptor (AR) antagonist, 2-chloro-N-6-(3-iodobenzyl)-4'-thioadenosine-5'-N,N-dimethyluronamide, structure-activity relationships were studied for a series of 5'-N,N-dialkyluronamide derivatives, synthesized from D-gulonic gamma-lactone. From this study, it was revealed that removal of the hydrogen bond-donating ability of the 5'-uronamide was essential for the pure A(3)AR antagonism. 5'-N,N-Dimethyluronamide derivatives exhibited higher binding affinity than larger 5'-N,N-dialkyl or 5'-N,N-cycloalkylamide derivatives, indicating that steric factors are crucial in binding to the human A(3)AR. A N-6-(3-bromobenzyl) derivative 6c (K-i = 9.32 nM) exhibited the highest binding affinity at the human A3AR with very low binding affinities to other AR subtypes. (c) 2008 Elsevier Ltd. All rights reserved.
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