Spiro[2.2]pentane as a dissymmetric scaffold for conformationally constrained analogues of glutamic acid: focus on racemic 1-aminospiro[2.2]pentyl-1,4-dicarboxylic acids

J Org Chem. 2002 Aug 9;67(16):5497-507. doi: 10.1021/jo020138v.

Abstract

In search for novel conformationally constrained analogues of L-glutamic acid, a diastereodivergent synthesis of the four 1-aminospiro[2.2]pentyl-1,4-dicarboxylic acid racemic pairs is reported along with their stereochemical assignment, conformational analysis, and preliminary biological evaluation as potential glutamate (ionotropic and metabotropic) ligands.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dicarboxylic Acids / chemical synthesis*
  • Dicarboxylic Acids / chemistry
  • Glutamic Acid / analogs & derivatives*
  • Glutamic Acid / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Pentanes / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Dicarboxylic Acids
  • Pentanes
  • Spiro Compounds
  • Glutamic Acid