Synthesis and resolution of racemic eliprodil and evaluation of the enantiomers of eliprodil as NMDA receptor antagonists

Bioorg Med Chem Lett. 2000 Jun 19;10(12):1377-80. doi: 10.1016/s0960-894x(00)00246-8.

Abstract

A short synthesis of the NMDA receptor antagonist (rac)-Eliprodil (9) and its resolution into the enantiomers by chiral HPLC is described. The enantiomers (R)-9 and (S)-9 were found to exhibit markedly different affinities for NR2B subunit containing NMDA receptors.

Publication types

  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Excitatory Amino Acid Antagonists / chemical synthesis*
  • Excitatory Amino Acid Antagonists / chemistry
  • Excitatory Amino Acid Antagonists / pharmacology
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Piperidines / pharmacology
  • Receptors, N-Methyl-D-Aspartate / antagonists & inhibitors*
  • Stereoisomerism

Substances

  • Excitatory Amino Acid Antagonists
  • Piperidines
  • Receptors, N-Methyl-D-Aspartate
  • eliprodil