Chromenones as potent bradykinin B1 antagonists

Bioorg Med Chem Lett. 2012 Jan 1;22(1):619-22. doi: 10.1016/j.bmcl.2011.10.068. Epub 2011 Oct 28.

Abstract

A series of fused 6,6-bicyclic chromenones was investigated for activity against the bradykinin B1 receptor. SAR studies based on a pharmacophore model revealed compounds with high affinity for both human and rabbit B1. These compounds demonstrated favorable pharmacokinetic properties and 5-chlorochromenone 15 was efficacious in a carrageenan-induced mechanical hyperalgesia model for chronic pain.

MeSH terms

  • Animals
  • Benzopyrans / chemical synthesis*
  • Benzopyrans / pharmacology
  • Bradykinin B1 Receptor Antagonists*
  • Carrageenan / pharmacology
  • Chemistry, Pharmaceutical / methods
  • Chronic Pain / drug therapy
  • Drug Design
  • Humans
  • Hyperalgesia / drug therapy
  • Inhibitory Concentration 50
  • Kinetics
  • Models, Chemical
  • Rabbits
  • Structure-Activity Relationship
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • 5-chlorochromenone
  • Benzopyrans
  • Bradykinin B1 Receptor Antagonists
  • Tumor Necrosis Factor-alpha
  • Carrageenan