NR2B-selective N-methyl-D-aspartate antagonists: synthesis and evaluation of 5-substituted benzimidazoles

J Med Chem. 2004 Apr 8;47(8):2089-96. doi: 10.1021/jm030483s.

Abstract

Two classes of 5-substituted benzimidazoles were identified as potent antagonists of the NR2B subtype of the N-methyl-d-aspartate (NMDA) receptor. Selected compounds show very good selectivity versus the NR2A, NR2C, and NR2D subtypes of the NMDA receptor as well as versus hERG-channel activity and alpha(1)-adrenergic binding. Benzimidazole 37a shows excellent activity in the carrageenan-induced mechanical hyperalgesia assay in rats as well as good pharmacokinetic behavior in dogs.

MeSH terms

  • Analgesics / chemical synthesis*
  • Analgesics / pharmacokinetics
  • Analgesics / pharmacology
  • Animals
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / pharmacokinetics
  • Benzimidazoles / pharmacology
  • Brain / metabolism
  • Calcium / metabolism
  • Carrageenan
  • Cell Line
  • Dogs
  • Female
  • Humans
  • Hyperalgesia / blood
  • Hyperalgesia / chemically induced
  • Hyperalgesia / drug therapy
  • In Vitro Techniques
  • Male
  • Patch-Clamp Techniques
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, N-Methyl-D-Aspartate / antagonists & inhibitors*
  • Receptors, N-Methyl-D-Aspartate / physiology
  • Structure-Activity Relationship

Substances

  • Analgesics
  • Benzimidazoles
  • NR2B NMDA receptor
  • Receptors, N-Methyl-D-Aspartate
  • Carrageenan
  • Calcium