3-Carboxy-pyrazolinalanine as a new scaffold for developing potent and selective NMDA receptor antagonists.

Lucia Tamborini; Andrea Pinto; Federica Mastronardi; Maria C. Iannuzzi; Gregorio Cullia; Birgitte Nielsen; Carlo  De Micheli; Paola Conti

doi:10.1016/j.ejmech.2013.07.010

3-Carboxy-pyrazolinalanine as a new scaffold for developing potent and selective NMDA receptor antagonists.

Lucia Tamborini, Andrea Pinto, Federica Mastronardi, Maria C. Iannuzzi, Gregorio Cullia, Birgitte Nielsen, Carlo De Micheli, Paola Conti

8 Citations (Scopus)

Abstract

A synthetic method for the preparation of suitably protected 3-carboxy-Δ²-pyrazolin-5-yl-alanine was developed. This scaffold is amenable to further decoration at the N1 position and was used to generate novel NMDA receptor ligands. Although weaker than the previously reported N1-Ph derivatives, the new ligands retain the ability to selectively bind to NMDA receptor with micromolar to submicromolar affinity. Considering the relevance of the N-functionalization for the biological activity, the results presented in this communication are preliminary to a full SAR study of this novel class of NMDA receptor antagonists.

Original language	English
Journal	European Journal of Medicinal Chemistry
Volume	68
Pages (from-to)	33-37
Number of pages	5
ISSN	0223-5234
DOIs	https://doi.org/10.1016/j.ejmech.2013.07.010
Publication status	Published - Oct 2013

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@article{64722c11d68a498a80ed1e41d7445a73,

title = "3-Carboxy-pyrazolinalanine as a new scaffold for developing potent and selective NMDA receptor antagonists.",

abstract = "A synthetic method for the preparation of suitably protected 3-carboxy-Δ2-pyrazolin-5-yl-alanine was developed. This scaffold is amenable to further decoration at the N1 position and was used to generate novel NMDA receptor ligands. Although weaker than the previously reported N1-Ph derivatives, the new ligands retain the ability to selectively bind to NMDA receptor with micromolar to submicromolar affinity. Considering the relevance of the N-functionalization for the biological activity, the results presented in this communication are preliminary to a full SAR study of this novel class of NMDA receptor antagonists.",

author = "Lucia Tamborini and Andrea Pinto and Federica Mastronardi and Iannuzzi, {Maria C.} and Gregorio Cullia and Birgitte Nielsen and {De Micheli}, Carlo and Paola Conti",

year = "2013",

month = oct,

doi = "10.1016/j.ejmech.2013.07.010",

language = "English",

volume = "68",

pages = "33--37",

journal = "European Journal of Medicinal Chemistry",

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T1 - 3-Carboxy-pyrazolinalanine as a new scaffold for developing potent and selective NMDA receptor antagonists.

AU - Tamborini, Lucia

AU - Pinto, Andrea

AU - Mastronardi, Federica

AU - Iannuzzi, Maria C.

AU - Cullia, Gregorio

AU - Nielsen, Birgitte

AU - De Micheli, Carlo

AU - Conti, Paola

PY - 2013/10

Y1 - 2013/10

N2 - A synthetic method for the preparation of suitably protected 3-carboxy-Δ2-pyrazolin-5-yl-alanine was developed. This scaffold is amenable to further decoration at the N1 position and was used to generate novel NMDA receptor ligands. Although weaker than the previously reported N1-Ph derivatives, the new ligands retain the ability to selectively bind to NMDA receptor with micromolar to submicromolar affinity. Considering the relevance of the N-functionalization for the biological activity, the results presented in this communication are preliminary to a full SAR study of this novel class of NMDA receptor antagonists.

AB - A synthetic method for the preparation of suitably protected 3-carboxy-Δ2-pyrazolin-5-yl-alanine was developed. This scaffold is amenable to further decoration at the N1 position and was used to generate novel NMDA receptor ligands. Although weaker than the previously reported N1-Ph derivatives, the new ligands retain the ability to selectively bind to NMDA receptor with micromolar to submicromolar affinity. Considering the relevance of the N-functionalization for the biological activity, the results presented in this communication are preliminary to a full SAR study of this novel class of NMDA receptor antagonists.

U2 - 10.1016/j.ejmech.2013.07.010

DO - 10.1016/j.ejmech.2013.07.010

M3 - Journal article

SN - 0223-5234

VL - 68

SP - 33

EP - 37

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

ER -

3-Carboxy-pyrazolinalanine as a new scaffold for developing potent and selective NMDA receptor antagonists.

Abstract

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