Synthesis and preliminary pharmacological evaluation of the four stereoisomers of (2S)-2-(2'-phosphono-3'-phenylcyclopropyl)glycine, the first class of 3'-substituted trans C1'-2'-2-(2'-phosphonocyclopropyl)glycines

Bioorg Med Chem. 2007 May 1;15(9):3161-70. doi: 10.1016/j.bmc.2007.02.040. Epub 2007 Feb 22.

Abstract

Four stereoisomers of (2S)-2-(2'-phosphono-3'-phenylcyclopropyl)glycine were synthesized by a stereocontrolled synthetic procedure and evaluated as mGluRs ligands. The (2S,1'R,2'S,3'R)-isomer (PPCG-2) showed to be a group III mGluRs selective ligand endowed with a moderate potency as mGluR4/mGluR6 agonist.

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Cyclopropanes / chemical synthesis*
  • Cyclopropanes / chemistry
  • Cyclopropanes / pharmacology*
  • Drug Evaluation, Preclinical
  • Glycine / analogs & derivatives*
  • Glycine / chemical synthesis
  • Glycine / chemistry
  • Glycine / pharmacology
  • Humans
  • Ligands
  • Models, Molecular
  • Molecular Structure
  • Rats
  • Receptors, Metabotropic Glutamate / agonists*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • (2S)-2-(2'-phosphono-3'-phenylcyclopropyl)glycine
  • Cyclopropanes
  • Ligands
  • Receptors, Metabotropic Glutamate
  • Glycine