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 (2S,5′S) stereoisomer is an agonist at the AMPA and KA receptors, its (2R,5′R) enantiomer interacts selectively with the NMDA receptors; the (2S,5′R) stereoisomer is the only one capable to activate the mGluRs.
Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid / A. Pinto, P. Conti, M. De Amici, L. Tamborini, U. Madsen, B. Nielsen, T. Christesen, H. Bräuner Osborne, C. De Micheli. - In: JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0022-2623. - 51:7(2008), pp. 2311-2315. [10.1021/jm701394a]
Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid
A. PintoPrimo
;P. ContiSecondo
;M. De Amici;L. Tamborini;C. De MicheliUltimo
2008
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 (2S,5′S) stereoisomer is an agonist at the AMPA and KA receptors, its (2R,5′R) enantiomer interacts selectively with the NMDA receptors; the (2S,5′R) stereoisomer is the only one capable to activate the mGluRs.File | Dimensione | Formato | |
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