Structure-activity relationships of truncated D- and l-4'-thioadenosine derivatives as species-independent A3 adenosine receptor antagonists.

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Jeong LS, Pal S, Choe SA, Choi WJ, Jacobson KA, Gao ZG, Klutz AM, Hou X, Kim HO, Lee HW, Lee SK, Tosh DK, Moon HR

Structure-activity relationships of truncated D- and l-4'-thioadenosine derivatives as species-independent A3 adenosine receptor antagonists.

J Med Chem. 2008 Oct 23;51(20):6609-13. doi: 10.1021/jm8008647. Epub 2008 Sep 24.

PubMed ID

18811138 [ View in PubMed

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Abstract

Novel D- and l-4'-thioadenosine derivatives lacking the 4'-hydroxymethyl moiety were synthesized, starting from d-mannose and d-gulonic gamma-lactone, respectively, as potent and selective species-independent A 3 adenosine receptor (AR) antagonists. Among the novel 4'-truncated 2-H nucleosides tested, a N(6)-(3-chlorobenzyl) derivative 7c was the most potent at the human A 3 AR (K i = 1.5 nM), but a N(6)-(3-bromobenzyl) derivative 7d showed the optimal species-independent binding affinity.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Piclidenoson	Adenosine receptor A3	Ki (nM)	1	N/A	N/A	Details