Synthesis of new isoxazoline-based acidic amino acids and investigation of their affinity and selectivity profile at ionotropic glutamate receptors

Andrea Pinto; Paola Conti; Giovanni Grazioso; Lucia Tamborini; Ulf Madsen; Birgitte Nielsen; Carlo De Micheli

doi:10.1016/j.ejmech.2010.12.020

Synthesis of new isoxazoline-based acidic amino acids and investigation of their affinity and selectivity profile at ionotropic glutamate receptors

Eur J Med Chem. 2011 Feb;46(2):787-93. doi: 10.1016/j.ejmech.2010.12.020. Epub 2010 Dec 23.

Authors

Andrea Pinto¹, Paola Conti, Giovanni Grazioso, Lucia Tamborini, Ulf Madsen, Birgitte Nielsen, Carlo De Micheli

Affiliation

¹ Dipartimento di Scienze Farmaceutiche Pietro Pratesi, Università degli Studi di Milano, Via Mangiagalli 25, 20133 Milano, Italy.

PMID: 21220180
DOI: 10.1016/j.ejmech.2010.12.020

Abstract

The synthesis of four new isoxazoline-based amino acids being analogues of previously described glutamate receptor ligands is reported and their affinity for ionotropic glutamate receptors is analyzed in comparison with that of selected model compounds. Molecular modelling investigations have been carried out to rationalize the interaction with the NMDA receptors.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemical synthesis
Amino Acids / chemistry
Amino Acids / pharmacology*
Binding Sites / drug effects
Isoxazoles / chemistry*
Ligands
Models, Molecular
Molecular Conformation
Receptors, Ionotropic Glutamate / chemistry
Receptors, Ionotropic Glutamate / metabolism*
Stereoisomerism
Structure-Activity Relationship

Substances

Amino Acids
Isoxazoles
Ligands
Receptors, Ionotropic Glutamate