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Synthesis of Novel N 1 ‐Substituted Bicyclic Pyrazole Amino Acids and Evaluation of Their Interaction with Glutamate Receptors
Author(s) -
Conti Paola,
Grazioso Giovanni,
Joppolo di Ventimiglia Samuele,
Pinto Andrea,
Roda Gabriella,
Madsen Ulf,
BräunerOsborne Hans,
Nielsen Birgitte,
Costagli Chiara,
Galli Alessandro
Publication year - 2005
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200590052
Subject(s) - chemistry , ionotropic effect , bicyclic molecule , amino acid , pyrazole , metabotropic glutamate receptor , glycine , glutamate receptor , nmda receptor , stereochemistry , metabotropic receptor , agonist , receptor , combinatorial chemistry , biochemistry
N 1 ‐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.