Synthesis and pharmacological characterisation of a conformationally restrained series of indole-2-carboxylates as in vivo potent glycine antagonists

Farmaco. 2001 Oct;56(10):791-8. doi: 10.1016/s0014-827x(01)01141-7.

Abstract

After the identification of GV150526, the indole-2-carboxylate template was further explored in order to identify novel potential anti-stroke agents. In particular, the SAR of the side chain present at the C-3 position of the indole nucleus was widely studied. In this paper, the synthesis and the pharmacological profile of a further class of conformationally restricted analogues of GV150526 as in vitro and in vivo potent glycine antagonists is reported. In particular, a pyrazolidinone derivative was identified as a potent neuroprotective agent in animal models of cerebral ischaemia.

MeSH terms

  • Animals
  • Binding Sites / drug effects
  • Glycine / antagonists & inhibitors*
  • Indoles / chemical synthesis*
  • Indoles / pharmacology
  • Male
  • Mice
  • Neuroprotective Agents / chemical synthesis
  • Neuroprotective Agents / therapeutic use
  • Rats
  • Rats, Sprague-Dawley
  • Seizures / prevention & control
  • Stroke / prevention & control
  • Structure-Activity Relationship

Substances

  • 3-(2-((phenylamino)carbonyl)ethenyl)-4,6-dichloroindole-2-carboxylic acid
  • Indoles
  • Neuroprotective Agents
  • Glycine