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

TY - JOUR

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 -