N6-substituted adenosine receptor agonists. Synthesis and pharmacological activity as potent antinociceptive agents

J Med Chem. 1994 Dec 9;37(25):4307-16. doi: 10.1021/jm00051a007.

Abstract

Novel N6-(indol-3-yl)alkyl derivatives of adenosine were synthesized. The adenosine receptor affinity and the antinociceptive activity of these compounds were assessed in binding studies and the phenylbenzoquinone-induced writhing test. Most of these analogues exhibited a potent analgesic activity without side effects. Among them, compound 3c (UP 202-32) bound to A1 (Ki = 110 nM) and A2 (Ki = 350 nM) adenosine receptors in a specific manner since it did not interact with many other receptors, especially opioid binding sites. The antinociceptive activity in the phenylbenzoquinone assay (ED50 = 3.3 mg/kg po) was antagonized by 8-cyclopentyltheophylline, suggesting that an adenosinergic mechanism underlies the analgesic activity observed with this compound. The data obtained with these new N6-substituted adenosine receptor agonists emphasize the interest of such compounds in the treatment of pain.

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / antagonists & inhibitors
  • Adenosine / chemical synthesis
  • Adenosine / metabolism
  • Analgesia
  • Analgesics / chemical synthesis*
  • Analgesics / metabolism
  • Animals
  • Indoles / antagonists & inhibitors
  • Indoles / chemical synthesis*
  • Indoles / metabolism
  • Methylation
  • Mice
  • Molecular Structure
  • Nitrogen / chemistry
  • Purinergic P1 Receptor Agonists*
  • Rats
  • Receptors, Purinergic P1 / metabolism
  • Structure-Activity Relationship
  • Theophylline / analogs & derivatives
  • Theophylline / pharmacology

Substances

  • Analgesics
  • Indoles
  • Purinergic P1 Receptor Agonists
  • Receptors, Purinergic P1
  • UP 202-32
  • 8-cyclopentyl-1,3-dimethylxanthine
  • Theophylline
  • Adenosine
  • Nitrogen