Synthesis of C5-tetrazole derivatives of 2-amino-adipic acid displaying NMDA glutamate receptor antagonism

Five derivatives of 2-amino-adipic acid bearing a tetrazole-substituted in C5 position were synthesized. These compounds displayed selective antagonism towards N-methyl-d-aspartate (NMDA) receptors compared with AMPA receptors, and they were devoid of any neurotoxicity. Among these five analogues, o...

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Veröffentlicht in:Amino acids 2011-03, Vol.40 (3), p.913-922
Hauptverfasser: Lenda, Fatimazohra, Crouzin, Nadine, Cavalier, Mélanie, Guiramand, Janique, Lanté, Fabien, Barbanel, Gérard, Cohen-Solal, Catherine, Martinez, Jean, Guenoun, Farhate, Lamaty, Frédéric, Vignes, Michel
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Sprache:eng
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Zusammenfassung:Five derivatives of 2-amino-adipic acid bearing a tetrazole-substituted in C5 position were synthesized. These compounds displayed selective antagonism towards N-methyl-d-aspartate (NMDA) receptors compared with AMPA receptors, and they were devoid of any neurotoxicity. Among these five analogues, one exhibited a higher affinity for synaptic NMDA responses than the other four. Therefore, C5 tetrazole-substituted of 2-amino-adipic acid represent an interesting series of new NMDA receptor antagonists. This approach may be considered as a new strategy to develop ligands specifically targeted to synaptic or extra-synaptic NMDA receptors.
ISSN:0939-4451
1438-2199
DOI:10.1007/s00726-010-0713-1