A novel series of bicyclo[1.1.1] pentane-based x-acidic amino acids, including (2S)- and (2R)-3-(3'-carboxybicyclo[1.1.1] pentyl) alanines (8 and 9), (2S)- and (2R)- 2-(30-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.
Design, synthesis and biological evaluation of novel bicyclo[1.1.1] pentane-based omega-acidic amino acids as glutamate receptors ligands
FILOSA, Rosanna;
2009
Abstract
A novel series of bicyclo[1.1.1] pentane-based x-acidic amino acids, including (2S)- and (2R)-3-(3'-carboxybicyclo[1.1.1] pentyl) alanines (8 and 9), (2S)- and (2R)- 2-(30-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.File in questo prodotto:
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