Aminobicyclo[2.2.1.]heptane dicarboxylic acids (ABHD), rigid analogs of ACPD and glutamic acid: synthesis and pharmacological activity on metabotropic receptors mGluR1 and mGluR2

Bioorg Med Chem. 1998 Feb;6(2):195-208. doi: 10.1016/s0968-0896(97)10031-1.

Abstract

Isomeric norbornane-derived rigid analogs mimicking different potential conformations of ACPD (1-aminocyclopentane-1,3-dicarboxylic acid) and glutamic acid have been synthesized, via the hydantoin route, to be used as conformational probes for bioactive conformations at the glutamatergic receptors of the central nervous system. Activities on metabotropic receptors mGluR1 and mGluR2 are reported and discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Cycloleucine / analogs & derivatives*
  • Cycloleucine / chemistry
  • Cycloleucine / pharmacology
  • Dicarboxylic Acids / chemical synthesis*
  • Dicarboxylic Acids / pharmacology
  • Gas Chromatography-Mass Spectrometry
  • Glutamic Acid / analogs & derivatives*
  • Glutamic Acid / pharmacology
  • Isomerism
  • Models, Chemical
  • Molecular Conformation
  • Norbornanes / chemical synthesis*
  • Norbornanes / chemistry*
  • Norbornanes / pharmacology
  • Receptors, Metabotropic Glutamate / drug effects*

Substances

  • 7-aminobicyclo(2.2.1)heptane-2,7-dicarboxyxlic acid
  • Dicarboxylic Acids
  • Norbornanes
  • Receptors, Metabotropic Glutamate
  • metabotropic glutamate receptor 2
  • metabotropic glutamate receptor type 1
  • Cycloleucine
  • 1-amino-1,3-dicarboxycyclopentane
  • Glutamic Acid