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Elsevier, Bioorganic and Medicinal Chemistry, 1(17), p. 242-250

DOI: 10.1016/j.bmc.2008.11.015

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Design, synthesis and biological evaluation of novel bicyclo[1.1.1]pentane-based ω-acidic amino acids as glutamate receptors ligands

Journal article published in 2008 by Rosanna Filosa ORCID, M. Carmela Fulco, Maura Marinozzi, Nicola Giacchè, Antonio Macchiarulo, Antonella Peduto, Antonio Massa, Paolo de Caprariis, Christian Thomsen, Claus T. Christoffersen, Roberto Pellicciari
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This paper is available in a repository.

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Abstract

A novel series of bicyclo[1.1.1]pentane-based omega-acidic amino acids, including (2S)- and (2R)-3-(3'-carboxybicyclo[1.1.1]pentyl)alanines (8 and 9), (2S)- and (2R)-2-(3'-carboxymethylbicyclo[1.1.1]pentyl)glycines (10 and 11), and (2S)- and (2R)-3-(3'-phosphonomethylbicyclo[1.1.1]pentyl)glycines (12 and 13), were synthesized and evaluated as glutamate receptor ligands. Among them, (2R)-3-(3'-phosphonomethylbicyclo[1.1.1]pentyl)glycine (13) showed relatively high affinity and selectivity at the NMDA receptor. The results are also discussed in light of pharmacophoric modelling studies of NMDA agonists and antagonists.