Analogues of 1,3-dipropyl-8-phenylxanthine: enhancement of selectivity at A1-adenosine receptors by aryl substituents

J Med Chem. 1986 Aug;29(8):1520-4. doi: 10.1021/jm00158a034.

Abstract

The effect of a variety of aryl substituents on the potency and selectivity of 19 analogues of 1,3-dipropyl-8-phenylxanthine as antagonists at A1- and A2-adenosine receptors in brain tissue was determined. The 4-sulfamoylphenyl and 4-carbamoylphenyl analogues are potent and somewhat selective for the A1 receptor. None of the dihydroxyphenyl analogues are remarkably potent, but all are selective for the A1 receptor. 1,3-Dipropyl-8-(2-hydroxy-4-methoxyphenyl)xanthine is the most selective A1 antagonist of the analogues with a A1/A2 potency ratio of about 90.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cerebral Cortex / metabolism
  • Rats
  • Receptors, Cell Surface / metabolism*
  • Receptors, Purinergic
  • Structure-Activity Relationship
  • Xanthines / chemical synthesis
  • Xanthines / pharmacology*

Substances

  • Receptors, Cell Surface
  • Receptors, Purinergic
  • Xanthines
  • 1,3-dipropyl-8-phenylxanthine