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Design and synthesis of N6-substituted-4′-thioadenosine-5′-uronamides as potent and selective human A3 adenosine receptor agonists

Title
Design and synthesis of N6-substituted-4′-thioadenosine-5′-uronamides as potent and selective human A3 adenosine receptor agonists
Authors
Choi W.J.Lee H.W.Kim H.O.Chinn M.Gao Z.-G.Patel A.Jacobson K.A.Moon H.R.Jung Y.H.Jeong L.S.
Ewha Authors
정낙신최원준
Issue Date
2009
Journal Title
Bioorganic and Medicinal Chemistry
ISSN
0968-0896JCR Link
Citation
vol. 17, no. 23, pp. 8003 - 8011
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
On the basis of a bioisosteric rationale, 4′-thionucleoside analogues of IB-MECA (N6-(3-Iodo-benzyl)-9-(5′-methylaminocarbonyl-β-d- ribofuranosyl)adenine), which is a potent and selective A3 adenosine receptor (AR) agonist, were synthesized from d-gulonic acid γ-lactone. The 4′-thio analogue (5h) of IB-MECA showed extremely high binding affinity (Ki = 0.25 nM) at the human A3AR and was more potent than IB-MECA (Ki = 1.4 nM). Bulky substituents at the 5′-uronamide position, such as cyclohexyl and 2-methylbenzyl, in this series of 2-H nucleoside derivatives were tolerated in A3AR binding, although small alkyl analogues were more potent. © 2009 Elsevier Ltd.
DOI
10.1016/j.bmc.2009.10.011
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약학대학 > 약학과 > Journal papers
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