Synthesis of new β- and γ-benzyloxy- S-glutamic acid derivatives and evaluation of their activity as inhibitors of excitatory amino acid transporters

An efficient stereoselective preparation of the two enantiomerically pure diasteroisomers of γ-benzyloxy- S-glutamic acid was performed using trans-4-hydroxy- l-proline as a source of chirality, while the erythro and threo isomers of β-benzyloxy- S-glutamic acid were prepared starting from ( R)-Garn...

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Bibliographic Details
Published in:Tetrahedron 2009-08, Vol.65 (31), p.6083-6089
Main Authors: Tamborini, Lucia, Conti, Paola, Pinto, Andrea, Colleoni, Simona, Gobbi, Marco, De Micheli, Carlo
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:An efficient stereoselective preparation of the two enantiomerically pure diasteroisomers of γ-benzyloxy- S-glutamic acid was performed using trans-4-hydroxy- l-proline as a source of chirality, while the erythro and threo isomers of β-benzyloxy- S-glutamic acid were prepared starting from ( R)-Garner's aldehyde. All new derivatives were tested for their inhibitory activity against excitatory amino acid transporters in a rat synaptosomal preparation and their IC 50 values were compared to that of TBOA, a one carbon lower homologue commonly used as the reference blocker of glutamate transporters. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.05.054