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Structure-activity relationships of 2-chloro-N6-substituted-4′-thioadenosine-5′-N,N-dialkyluronamides as human A3 adenosine receptor antagonists
- Structure-activity relationships of 2-chloro-N6-substituted-4′-thioadenosine-5′-N,N-dialkyluronamides as human A3 adenosine receptor antagonists
- Jeong L.S.; Lee H.W.; Kim H.O.; Tosh D.K.; Pal S.; Choi W.J.; Gao Z.-G.; Patel A.R.; Williams W.; Jacobson K.A.; Kim H.-D.
- Ewha Authors
- 정낙신; 최원준
- Issue Date
- Journal Title
- Bioorganic and Medicinal Chemistry Letters
- Bioorganic and Medicinal Chemistry Letters vol. 18, no. 5, pp. 1612 - 1616
- SCI; SCIE; SCOPUS
- Document Type
- On the basis of potent and selective A3 adenosine receptor (AR) antagonist, 2-chloro-N6-(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 γ-lactone. From this study, it was revealed that removal of the hydrogen bond-donating ability of the 5′-uronamide was essential for the pure A3AR 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 A3AR. A N6-(3-bromobenzyl) derivative 6c (Ki = 9.32 nM) exhibited the highest binding affinity at the human A3AR with very low binding affinities to other AR subtypes. © 2008 Elsevier Ltd. All rights reserved.
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