Synthesis and inhibitory activities at mGluRs of 3-alkylated and N-alkylated cyclopentyl-glutamate analogues

Authors

Alison T. Ung, University of Technology, SydneyFollow
Stephen G. Pyne, University of WollongongFollow
Francois Bischoff, CNS Discovery Research
Anne S. J Lesage, CNS Discovery Research
Brian W. Skelton, University of Western Australia
Allan H. White, University of Western Australia

RIS ID

75816

Publication Details

Ung, A. T., Pyne, S. G., Bischoff, F., Lesage, A. S. J., Skelton, B. W. & White, A. H. (2013). Synthesis and inhibitory activities at mGluRs of 3-alkylated and N-alkylated cyclopentyl-glutamate analogues. Tetrahedron, 69 (12), 2577-2587.

Abstract

The conformationally restricted glutamate analogues, 3-alkyl-1-amino-2-cyclopentene-1,3-dicarboxylates and N-alkylated analogues have been prepared in a regioselective and diastereoselective manner. From the biological studies of the 3-alkylated analogues, compound 13b was found to be the most potent antagonist (IC50 7.7 μM) at mGluR2. Amongst the N-alkylated analogues, compound 20 was found to be a partial agonist (EC50 9.5 μM) and as well as an antagonist (IC50 47 μM) at mGluR2.