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

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.

SUBMITTER: Jeong LS 

PROVIDER: S-EPMC3616494 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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

Jeong Lak Shin LS   Pal Shantanu S   Choe Seung Ah SA   Choi Won Jun WJ   Jacobson Kenneth A KA   Gao Zhan-Guo ZG   Klutz Athena M AM   Hou Xiyan X   Kim Hea Ok HO   Lee Hyuk Woo HW   Lee Sang Kook SK   Tosh Dilip K DK   Moon Hyung Ryong HR  

Journal of medicinal chemistry 20080924 20

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. ...[more]

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