Synthesis of novel N1-substituted bicyclic pyrazole amino acids and evaluation of their interaction with glutamate receptors

Paola Conti; Giovanni Grazioso; Samuele Joppolo di Ventimiglia; Andrea Pinto; Gabriella Roda; Ulf Madsen; Hans Bräuner-Osborne; Birgitte Nielsen; Chiara Costagli; Alessandro Galli

doi:10.1002/cbdv.200590052

Synthesis of novel N1-substituted bicyclic pyrazole amino acids and evaluation of their interaction with glutamate receptors

Paola Conti, Giovanni Grazioso, Samuele Joppolo di Ventimiglia, Andrea Pinto, Gabriella Roda, Ulf Madsen, Hans Bräuner-Osborne, Birgitte Nielsen, Chiara Costagli, Alessandro Galli

4 Citations (Scopus)

Abstract

N1-substituted bicyclic pyrazole amino acids (S)-9a-9c and (R)-9a-9c, which are conformationally constrained analogues of glutamic acid, were prepared via a strategy based on a 1,3-dipolar cycloaddition. The new amino acids were tested for activity at ionotropic and metabotropic glutamate receptors. Some of them turned out to be selective for the NMDA receptors, where they behaved as weak antagonists. The biological activity is mainly due to the interaction with the glutamate binding site, and not with the glycine co-agonist site.

Original language	English
Journal	Chemistry & Biodiversity
Volume	2
Issue number	6
Pages (from-to)	748-57
ISSN	1612-1872
DOIs	https://doi.org/10.1002/cbdv.200590052
Publication status	Published - Jun 2005

Keywords

Bicyclo Compounds, Heterocyclic
Excitatory Amino Acid Agonists
Excitatory Amino Acid Antagonists
Molecular Structure
Receptors, Glutamate

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10.1002/cbdv.200590052

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title = "Synthesis of novel N1-substituted bicyclic pyrazole amino acids and evaluation of their interaction with glutamate receptors",

abstract = "N1-substituted bicyclic pyrazole amino acids (S)-9a-9c and (R)-9a-9c, which are conformationally constrained analogues of glutamic acid, were prepared via a strategy based on a 1,3-dipolar cycloaddition. The new amino acids were tested for activity at ionotropic and metabotropic glutamate receptors. Some of them turned out to be selective for the NMDA receptors, where they behaved as weak antagonists. The biological activity is mainly due to the interaction with the glutamate binding site, and not with the glycine co-agonist site.",

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doi = "10.1002/cbdv.200590052",

language = "English",

volume = "2",

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T1 - Synthesis of novel N1-substituted bicyclic pyrazole amino acids and evaluation of their interaction with glutamate receptors

AU - Conti, Paola

AU - Grazioso, Giovanni

AU - di Ventimiglia, Samuele Joppolo

AU - Pinto, Andrea

AU - Roda, Gabriella

AU - Madsen, Ulf

AU - Bräuner-Osborne, Hans

AU - Nielsen, Birgitte

AU - Costagli, Chiara

AU - Galli, Alessandro

PY - 2005/6

Y1 - 2005/6

N2 - N1-substituted bicyclic pyrazole amino acids (S)-9a-9c and (R)-9a-9c, which are conformationally constrained analogues of glutamic acid, were prepared via a strategy based on a 1,3-dipolar cycloaddition. The new amino acids were tested for activity at ionotropic and metabotropic glutamate receptors. Some of them turned out to be selective for the NMDA receptors, where they behaved as weak antagonists. The biological activity is mainly due to the interaction with the glutamate binding site, and not with the glycine co-agonist site.

AB - N1-substituted bicyclic pyrazole amino acids (S)-9a-9c and (R)-9a-9c, which are conformationally constrained analogues of glutamic acid, were prepared via a strategy based on a 1,3-dipolar cycloaddition. The new amino acids were tested for activity at ionotropic and metabotropic glutamate receptors. Some of them turned out to be selective for the NMDA receptors, where they behaved as weak antagonists. The biological activity is mainly due to the interaction with the glutamate binding site, and not with the glycine co-agonist site.

KW - Bicyclo Compounds, Heterocyclic

KW - Excitatory Amino Acid Agonists

KW - Excitatory Amino Acid Antagonists

KW - Molecular Structure

KW - Receptors, Glutamate

U2 - 10.1002/cbdv.200590052

DO - 10.1002/cbdv.200590052

M3 - Journal article

C2 - 17192018

SN - 1612-1872

VL - 2

SP - 748

EP - 757

JO - Chemistry & Biodiversity

JF - Chemistry & Biodiversity

IS - 6

ER -

Synthesis of novel N1-substituted bicyclic pyrazole amino acids and evaluation of their interaction with glutamate receptors

Abstract

Keywords

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