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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.

journal of medicinal chemistry

Structure−Activity Relationships of Truncated <scp>d</scp>- and <scp>l</scp>-4′-Thioadenosine Derivatives as Species-Independent A<sub>3</sub> Adenosine Receptor Antagonists

Structure−Activity Relationships of Truncated d- and l-4′-Thioadenosine Derivatives as Species-Independent A3 Adenosine Receptor Antagonists

Structure−Activity Relationships of Truncated d- and l-4′-Thioadenosine Derivatives as Species-Independent A₃ Adenosine Receptor Antagonists