1-Aminocyclopropane-1-carboxylic acid derivatives: a new, general synthesis and NMDA receptor complex binding affinity study

Farmaco. 1993 Dec;48(12):1663-74.

Abstract

A new synthesis of 1-aminocyclopropane-1-carboxylic acid and of its (E)- and (Z)-2-substituted analogues (R = CH3;i-Pr;C6H5) has been performed by means of the "diazo-addition" method, starting from N-(diphenylmethylene)-2,3-dehydro-1-amino-1-carboxylate precursors. The (E)- and (Z)-2-phenyl and the (Z)-2-methylcyclopropaneamino acids have been obtained with high diastereospecificity. All the cyclopropaneamino acids prepared were tested for their affinity for some glutamate receptors and resulted inactive, with the exception of compounds (E)-1b and (Z)-1c which showed a shallow displacement of [3H]-glycine binding.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Amino Acids / metabolism
  • Animals
  • Binding Sites
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / metabolism
  • Cyclopropanes / chemical synthesis*
  • Cyclopropanes / chemistry
  • Cyclopropanes / metabolism
  • Glycine / metabolism
  • Male
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, N-Methyl-D-Aspartate / metabolism
  • Stereoisomerism

Substances

  • Amino Acids
  • Carboxylic Acids
  • Cyclopropanes
  • Receptors, N-Methyl-D-Aspartate
  • Glycine