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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adenosine / analogs & derivatives*
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Adenosine / chemical synthesis
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Adenosine / chemistry
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Adenosine / pharmacology
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Adenosine A3 Receptor Antagonists*
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Animals
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Humans
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Molecular Structure
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Rats
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Receptor, Adenosine A3 / metabolism
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Structure-Activity Relationship
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Thionucleosides / chemical synthesis*
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Thionucleosides / chemistry
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Thionucleosides / pharmacology*
Substances
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Adenosine A3 Receptor Antagonists
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Receptor, Adenosine A3
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Thionucleosides
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4'-thioadenosine
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Adenosine