Synthesis and anticonvulsant activity of novel bicyclic acidic amino acids

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

Standard

Synthesis and anticonvulsant activity of novel bicyclic acidic amino acids. / Conti, Paola; De Amici, Marco; Joppolo Di Ventimiglia, Samuele; Stensbøl, Tine B; Madsen, Ulf; Bräuner-Osborne, Hans; Russo, Emilio; De Sarro, Giovambattista; Bruno, Giuseppe; De Micheli, Carlo.

In: Journal of Medicinal Chemistry, Vol. 46, No. 14, 03.07.2003, p. 3102-8.

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

Harvard

Conti, P, De Amici, M, Joppolo Di Ventimiglia, S, Stensbøl, TB, Madsen, U, Bräuner-Osborne, H, Russo, E, De Sarro, G, Bruno, G & De Micheli, C 2003, 'Synthesis and anticonvulsant activity of novel bicyclic acidic amino acids', Journal of Medicinal Chemistry, vol. 46, no. 14, pp. 3102-8. https://doi.org/10.1021/jm0308085

APA

Conti, P., De Amici, M., Joppolo Di Ventimiglia, S., Stensbøl, T. B., Madsen, U., Bräuner-Osborne, H., Russo, E., De Sarro, G., Bruno, G., & De Micheli, C. (2003). Synthesis and anticonvulsant activity of novel bicyclic acidic amino acids. Journal of Medicinal Chemistry, 46(14), 3102-8. https://doi.org/10.1021/jm0308085

Vancouver

Conti P, De Amici M, Joppolo Di Ventimiglia S, Stensbøl TB, Madsen U, Bräuner-Osborne H et al. Synthesis and anticonvulsant activity of novel bicyclic acidic amino acids. Journal of Medicinal Chemistry. 2003 Jul 3;46(14):3102-8. https://doi.org/10.1021/jm0308085

Author

Conti, Paola ; De Amici, Marco ; Joppolo Di Ventimiglia, Samuele ; Stensbøl, Tine B ; Madsen, Ulf ; Bräuner-Osborne, Hans ; Russo, Emilio ; De Sarro, Giovambattista ; Bruno, Giuseppe ; De Micheli, Carlo. / Synthesis and anticonvulsant activity of novel bicyclic acidic amino acids. In: Journal of Medicinal Chemistry. 2003 ; Vol. 46, No. 14. pp. 3102-8.

Bibtex

@article{6910d2bc6feb45ab93b4471fffcad7a8,
title = "Synthesis and anticonvulsant activity of novel bicyclic acidic amino acids",
abstract = "Bicyclic acidic amino acids (+/-)-6 and (+/-)-7, which are conformationally constrained homologues of glutamic acid, were prepared via a strategy based on a 1,3-dipolar cycloaddition. The new amino acids were tested toward ionotropic and metabotropic glutamate receptor subtypes; both of them behaved as antagonists at mGluR1,5 and as agonists at mGluR2. Furthermore, whereas (+/-)-6 was inactive at all ionotropic glutamate receptors, (+/-)-7 displayed a quite potent antagonism at the NMDA receptors. In the in vivo tests on DBA/2 mice, the compounds displayed an anticonvulsant activity. The interesting pharmacological profile of (+/-)-7 qualifies it as a lead of novel neuroprotective agents.",
keywords = "Amino Acids, Acidic, Amino Acids, Dicarboxylic, Animals, Anticonvulsants, CHO Cells, Cerebral Cortex, Cricetinae, Crystallography, X-Ray, Dicarboxylic Acids, Excitatory Amino Acid Agonists, Excitatory Amino Acid Antagonists, Heterocyclic Compounds, 2-Ring, Isoxazoles, Male, Mice, Mice, Inbred DBA, Molecular Conformation, Rats, Receptors, Metabotropic Glutamate, Receptors, N-Methyl-D-Aspartate, Stereoisomerism",
author = "Paola Conti and {De Amici}, Marco and {Joppolo Di Ventimiglia}, Samuele and Stensb{\o}l, {Tine B} and Ulf Madsen and Hans Br{\"a}uner-Osborne and Emilio Russo and {De Sarro}, Giovambattista and Giuseppe Bruno and {De Micheli}, Carlo",
year = "2003",
month = jul,
day = "3",
doi = "10.1021/jm0308085",
language = "English",
volume = "46",
pages = "3102--8",
journal = "Journal of Medicinal Chemistry",
issn = "0022-2623",
publisher = "American Chemical Society",
number = "14",

}

RIS

TY - JOUR

T1 - Synthesis and anticonvulsant activity of novel bicyclic acidic amino acids

AU - Conti, Paola

AU - De Amici, Marco

AU - Joppolo Di Ventimiglia, Samuele

AU - Stensbøl, Tine B

AU - Madsen, Ulf

AU - Bräuner-Osborne, Hans

AU - Russo, Emilio

AU - De Sarro, Giovambattista

AU - Bruno, Giuseppe

AU - De Micheli, Carlo

PY - 2003/7/3

Y1 - 2003/7/3

N2 - Bicyclic acidic amino acids (+/-)-6 and (+/-)-7, which are conformationally constrained homologues of glutamic acid, were prepared via a strategy based on a 1,3-dipolar cycloaddition. The new amino acids were tested toward ionotropic and metabotropic glutamate receptor subtypes; both of them behaved as antagonists at mGluR1,5 and as agonists at mGluR2. Furthermore, whereas (+/-)-6 was inactive at all ionotropic glutamate receptors, (+/-)-7 displayed a quite potent antagonism at the NMDA receptors. In the in vivo tests on DBA/2 mice, the compounds displayed an anticonvulsant activity. The interesting pharmacological profile of (+/-)-7 qualifies it as a lead of novel neuroprotective agents.

AB - Bicyclic acidic amino acids (+/-)-6 and (+/-)-7, which are conformationally constrained homologues of glutamic acid, were prepared via a strategy based on a 1,3-dipolar cycloaddition. The new amino acids were tested toward ionotropic and metabotropic glutamate receptor subtypes; both of them behaved as antagonists at mGluR1,5 and as agonists at mGluR2. Furthermore, whereas (+/-)-6 was inactive at all ionotropic glutamate receptors, (+/-)-7 displayed a quite potent antagonism at the NMDA receptors. In the in vivo tests on DBA/2 mice, the compounds displayed an anticonvulsant activity. The interesting pharmacological profile of (+/-)-7 qualifies it as a lead of novel neuroprotective agents.

KW - Amino Acids, Acidic

KW - Amino Acids, Dicarboxylic

KW - Animals

KW - Anticonvulsants

KW - CHO Cells

KW - Cerebral Cortex

KW - Cricetinae

KW - Crystallography, X-Ray

KW - Dicarboxylic Acids

KW - Excitatory Amino Acid Agonists

KW - Excitatory Amino Acid Antagonists

KW - Heterocyclic Compounds, 2-Ring

KW - Isoxazoles

KW - Male

KW - Mice

KW - Mice, Inbred DBA

KW - Molecular Conformation

KW - Rats

KW - Receptors, Metabotropic Glutamate

KW - Receptors, N-Methyl-D-Aspartate

KW - Stereoisomerism

U2 - 10.1021/jm0308085

DO - 10.1021/jm0308085

M3 - Journal article

C2 - 12825948

VL - 46

SP - 3102

EP - 3108

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 14

ER -

ID: 45596619