Design and synthesis of truncated 4'-thioadenosine derivatives as potent and selective A3 adenosine receptor antagonists

Nucleic Acids Symp Ser (Oxf). 2008:(52):641-2. doi: 10.1093/nass/nrn324.

Abstract

We have established structure-activity relationships of novel truncated D-4'-thioadenosine derivatives from D-mannose as potent and selective A(3) adenosine receptor (AR) antagonists. At the human A(3) AR, most of N(6)-substituted analogues showed high potency and selectivity and acted as pure antagonists in a cyclic AMP functional assay. Among compounds tested, 2-chloro-N(6)-3-chlorobenzyl and N(6)-3-chlorobenzyl analogues displayed very high binding affinities (K(i) = 1.66 nM and 1.5 nM, respectively) at the human A(3) AR. Truncated 4'-thioadenosine derivatives studied here are regarded as an excellent template for the design of novel A(3) AR antagonists to act at both human and murine species.

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemistry
  • Adenosine A3 Receptor Antagonists*
  • Animals
  • Cell Line
  • Cricetinae
  • Drug Design
  • Humans
  • Receptor, Adenosine A3 / metabolism
  • Structure-Activity Relationship
  • Thionucleosides / chemical synthesis
  • Thionucleosides / chemistry*
  • Thionucleosides / metabolism

Substances

  • Adenosine A3 Receptor Antagonists
  • Receptor, Adenosine A3
  • Thionucleosides
  • 4'-thioadenosine
  • Adenosine