Document Report Card

ID: ALA1142433

Journal: J Med Chem

Title: Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid.

Authors: Pinto A, Conti P, De Amici M, Tamborini L, Madsen U, Nielsen B, Christesen T, Bräuner-Osborne H, De Micheli C.

Abstract: The two enantiomeric pairs of erythro- and threo-amino-(3'-hydroxy-4',5'-dihydro-isoxazol-5'-yl)-acetic acids were synthesized via the 1,3-dipolar cycloaddition of bromonitrile oxide to ( R)- or ( S)-3-( tert-butoxycarbonyl)-2,2-dimethyl-4-vinyloxazolidine. The pharmacological profiles of the studied amino acids reflect the relationship between the activity/selectivity and the stereochemistry of the two stereogenic centers: while the (2 S,5' S) stereoisomer is an agonist at the AMPA and KA receptors, its (2 R,5' R) enantiomer interacts selectively with the NMDA receptors; the (2 S,5' R) stereoisomer is the only one capable to activate the mGluRs.

CiteXplore: 18338843

DOI: 10.1021/jm701394a