Synthesis of novel N1-substituted bicyclic pyrazole amino acids and evaluation of their interaction with glutamate receptors

Paola Conti, Giovanni Grazioso, Samuele Joppolo di Ventimiglia, Andrea Pinto, Gabriella Roda, Ulf Madsen, Hans Bräuner-Osborne, Birgitte Nielsen, Chiara Costagli, Alessandro Galli

Research output: Contribution to journalJournal articleResearchpeer-review

4 Citations (Scopus)

Abstract

N1-substituted bicyclic pyrazole amino acids (S)-9a-9c and (R)-9a-9c, which are conformationally constrained analogues of glutamic acid, were prepared via a strategy based on a 1,3-dipolar cycloaddition. The new amino acids were tested for activity at ionotropic and metabotropic glutamate receptors. Some of them turned out to be selective for the NMDA receptors, where they behaved as weak antagonists. The biological activity is mainly due to the interaction with the glutamate binding site, and not with the glycine co-agonist site.
Original languageEnglish
JournalChemistry & Biodiversity
Volume2
Issue number6
Pages (from-to)748-57
ISSN1612-1872
DOIs
Publication statusPublished - Jun 2005

Keywords

  • Bicyclo Compounds, Heterocyclic
  • Excitatory Amino Acid Agonists
  • Excitatory Amino Acid Antagonists
  • Molecular Structure
  • Receptors, Glutamate

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