New strategies for the synthesis of A3 adenosine receptor antagonists

Bioorg Med Chem. 2003 Sep 15;11(19):4161-9. doi: 10.1016/s0968-0896(03)00484-x.

Abstract

New A(3) adenosine receptor antagonists were synthesized and tested at human adenosine receptor subtypes. An advanced synthetic strategy permitted us to obtain a large amount of the key intermediate 5 that was then submitted to alkylation procedures in order to obtain the derivatives 6-8. These compounds were then functionalised into ureas at the 5-position (compounds 9-11, 18 and 19) to evaluate their affinity and selectivity versus hA(3) adenosine receptor subtype; in particular, compounds 18 and 19 displayed a value of affinity of 4.9 and 1.3 nM, respectively. Starting from 5, the synthetic methodologies employed permitted us to perform a rapid and a convenient divergent synthesis. A further improvement allowed the regioselective preparation of the N(8)-substituted compound 7. This method could be used as an helpful general procedure for the design of novel A(3) adenosine receptor antagonists without the difficulty of separating the N(8)-substituted pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidines from the corresponding N(7)-isomers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine A3 Receptor Antagonists*
  • Animals
  • Binding, Competitive
  • CHO Cells
  • Cricetinae
  • Drug Design
  • Humans
  • Isomerism
  • Pyrazoles / chemistry*
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / metabolism
  • Pyrimidines / pharmacology
  • Receptor, Adenosine A3 / metabolism
  • Structure-Activity Relationship
  • Triazoles / chemistry*

Substances

  • Adenosine A3 Receptor Antagonists
  • Pyrazoles
  • Pyrimidines
  • Receptor, Adenosine A3
  • Triazoles