A synthetic method for the preparation of suitably protected 3-carboxy-Delta(2)-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.

3-Carboxy-pyrazolinalanine as a new scaffold for developing potent and selective NMDA receptor antagonists / L. Tamborini, A. Pinto, F. Mastronardi, M.C. Iannuzzi, G. Cullia, B. Nielsen, C. De Micheli, P. Conti. - In: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0223-5234. - 68(2013), pp. 33-37. [10.1016/j.ejmech.2013.07.010]

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

L. Tamborini
;
A. Pinto;F. Mastronardi;M.C. Iannuzzi;G. Cullia;C. De Micheli;P. Conti
2013

Abstract

A synthetic method for the preparation of suitably protected 3-carboxy-Delta(2)-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.
L-Glutamic acid ; N-Methyl-D-aspartate receptor antagonist ; Pyrazoline ; Amino acid ; Intramolecular cyclization
Settore CHIM/08 - Chimica Farmaceutica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/225603
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