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.
Synthesis of Novel N1-Substituted Bicyclic Pyrazole Amino Acids and Evaluation of Their Interaction with Glutamate Receptors / P. Conti, G. Grazioso, S. Joppolo di Ventimiglia, A. Pinto, G. Roda, U. Madsen, H. Bräuner Osborne, B. Nielsen, C. Costagli, A. Galli. - In: CHEMISTRY & BIODIVERSITY. - ISSN 1612-1872. - 2:6(2005), pp. 748-757. [10.1002/cbdv.200590052]
Synthesis of Novel N1-Substituted Bicyclic Pyrazole Amino Acids and Evaluation of Their Interaction with Glutamate Receptors
P. Conti
Primo
;G. GraziosoSecondo
;A. Pinto;G. Roda;
2005
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.File | Dimensione | Formato | |
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