TY - JOUR
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
VL - 2
SP - 748
EP - 757
JO - Chemistry and Biodiversity
JF - Chemistry and Biodiversity
SN - 1612-1872
IS - 6
ER -