Impact of the aryl substituent kind and distance from pyrimido[2,1-f]purindiones on the adenosine receptor selectivity and antagonistic properties

Eur J Med Chem. 2003 Apr;38(4):397-402. doi: 10.1016/s0223-5234(03)00051-5.

Abstract

Adenosine receptor (AR) antagonists belong to two major groups of compounds: xanthines and non-xanthines. Recently several annelated xanthine derivatives have been described as selective A(1), A(2A), A(2B) and A(3) ARs antagonists. Contrary to dipropyl derivatives, in the group of dimethyl (un)substituted arylalkyl pyrimido[2,1-f]purindiones selective mainly adenosine A(2A) receptor antagonists were identified. Their activity depended on aryl substitution and its distance from pyrimido[2,1-f]purindione.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine A2 Receptor Antagonists
  • Animals
  • Humans
  • Molecular Structure
  • Purinergic P1 Receptor Antagonists*
  • Purines / chemistry*
  • Purines / metabolism*
  • Purines / pharmacology
  • Pyrimidines / chemistry*
  • Pyrimidines / metabolism*
  • Pyrimidines / pharmacology
  • Rats
  • Receptor, Adenosine A2A / metabolism
  • Receptors, Purinergic P1 / metabolism
  • Stereoisomerism
  • Structure-Activity Relationship
  • Theophylline / chemistry
  • Theophylline / metabolism
  • Theophylline / pharmacology
  • Xanthines / chemistry
  • Xanthines / metabolism
  • Xanthines / pharmacology

Substances

  • Adenosine A2 Receptor Antagonists
  • Purinergic P1 Receptor Antagonists
  • Purines
  • Pyrimidines
  • Receptor, Adenosine A2A
  • Receptors, Purinergic P1
  • Xanthines
  • Theophylline