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

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid. / Pinto, Andrea; Conti, Paola; De Amici, Marco; Tamborini, Lucia; Madsen, Ulf; Nielsen, Birgitte; Christesen, Thomas; Bräuner-Osborne, Hans; De Micheli, Carlo.

In: Journal of Medicinal Chemistry, Vol. 51, No. 7, 2008, p. 2311-2315.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Pinto, A, Conti, P, De Amici, M, Tamborini, L, Madsen, U, Nielsen, B, Christesen, T, Bräuner-Osborne, H & De Micheli, C 2008, 'Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid', Journal of Medicinal Chemistry, vol. 51, no. 7, pp. 2311-2315. https://doi.org/10.1021/jm701394a

APA

Pinto, A., Conti, P., De Amici, M., Tamborini, L., Madsen, U., Nielsen, B., Christesen, T., Bräuner-Osborne, H., & De Micheli, C. (2008). Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid. Journal of Medicinal Chemistry, 51(7), 2311-2315. https://doi.org/10.1021/jm701394a

Vancouver

Pinto A, Conti P, De Amici M, Tamborini L, Madsen U, Nielsen B et al. Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid. Journal of Medicinal Chemistry. 2008;51(7):2311-2315. https://doi.org/10.1021/jm701394a

Author

Pinto, Andrea ; Conti, Paola ; De Amici, Marco ; Tamborini, Lucia ; Madsen, Ulf ; Nielsen, Birgitte ; Christesen, Thomas ; Bräuner-Osborne, Hans ; De Micheli, Carlo. / Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid. In: Journal of Medicinal Chemistry. 2008 ; Vol. 51, No. 7. pp. 2311-2315.

Bibtex

@article{29c52ab011f511ddbee902004c4f4f50,
title = "Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid",
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.",
keywords = "Amino Acids, Animals, CHO Cells, Cell Line, Cloning, Molecular, Cricetinae, Cricetulus, Cyclization, Glycine, Humans, Isoxazoles, Molecular Structure, Rats, Receptors, Glutamate, Stereoisomerism, Structure-Activity Relationship",
author = "Andrea Pinto and Paola Conti and {De Amici}, Marco and Lucia Tamborini and Ulf Madsen and Birgitte Nielsen and Thomas Christesen and Hans Br{\"a}uner-Osborne and {De Micheli}, Carlo",
year = "2008",
doi = "10.1021/jm701394a",
language = "English",
volume = "51",
pages = "2311--2315",
journal = "Journal of Medicinal Chemistry",
issn = "0022-2623",
publisher = "American Chemical Society",
number = "7",

}

RIS

TY - JOUR

T1 - Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid

AU - Pinto, Andrea

AU - Conti, Paola

AU - De Amici, Marco

AU - Tamborini, Lucia

AU - Madsen, Ulf

AU - Nielsen, Birgitte

AU - Christesen, Thomas

AU - Bräuner-Osborne, Hans

AU - De Micheli, Carlo

PY - 2008

Y1 - 2008

N2 - 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.

AB - 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.

KW - Amino Acids

KW - Animals

KW - CHO Cells

KW - Cell Line

KW - Cloning, Molecular

KW - Cricetinae

KW - Cricetulus

KW - Cyclization

KW - Glycine

KW - Humans

KW - Isoxazoles

KW - Molecular Structure

KW - Rats

KW - Receptors, Glutamate

KW - Stereoisomerism

KW - Structure-Activity Relationship

U2 - 10.1021/jm701394a

DO - 10.1021/jm701394a

M3 - Journal article

C2 - 18338843

VL - 51

SP - 2311

EP - 2315

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 7

ER -

ID: 3800724