Tricyclic quinoxalinediones, aza-kynurenic acids, and indole-2-carboxylic acids as in vivo active NMDA-glycine antagonists

Curr Top Med Chem. 2006;6(7):733-45. doi: 10.2174/156802606776894500.

Abstract

This review article describes the development of in vivo active antagonists for the glycine binding site of the N-Methyl-D-Aspartate (NMDA) receptor. There were several difficulties in identifying a class of antagonists with in vivo efficacy and only a few compounds succeeded in emerging with activity in vivo. A series of tricyclic quinoxalinediones was highly potent glycine antagonists in vitro and the derivatives having a zwitterionic moiety including SM-18400 indeed showed in vivo activity. Similarly, tricyclic indole-2-carboxylic acids having a zwitterionic moiety such as SM-31900 were also active in vivo. In fact, SM-18400 and SM-31900 exhibited efficacy in several animal stroke models using intravenous infusion protocols. The practical syntheses of SM-18400 and SM-31900 as well as the novel synthesis of moderately active glycine antagonists, tricyclic azakynurenic acids, were also developed.

Publication types

  • Review

MeSH terms

  • Carboxylic Acids
  • Indoles / chemical synthesis
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Kynurenic Acid / chemical synthesis
  • Kynurenic Acid / chemistry
  • Kynurenic Acid / pharmacology*
  • Models, Molecular
  • Quinoxalines / chemical synthesis
  • Quinoxalines / chemistry
  • Quinoxalines / pharmacology*
  • Receptors, Glycine / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Carboxylic Acids
  • Indoles
  • Quinoxalines
  • Receptors, Glycine
  • indole-2-carboxylic acid
  • Kynurenic Acid