Synthesis and Biological Activities of Conformationally Restricted Cyclopentenyl-Glutamate Analogues

An efficient method for preparing conformationally restricted cyclopentenyl-glutamate analogues in a regioselective and diastereoselective manner has been developed using a formal [3 + 2] cycloaddition reaction of dehydroamino acids. Methods for preparing optically active versions of these compounds...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-01, Vol.67 (1), p.227-233
Main Authors: Ung, Alison T, Schafer, Karl, Lindsay, Karl B, Pyne, Stephen G, Amornraksa, Kitti, Wouters, Ria, Van der Linden, Ilse, Biesmans, Ilse, Lesage, Anne S. J, Skelton, Brian W, White, Allan H
Format: Article
Language:English
Subjects:
Aliphatic compounds
Animals
Biological and medical sciences
Calcium Signaling - drug effects
Chemistry
CHO Cells
Cricetinae
Cyclopentanes - chemical synthesis
Cyclopentanes - metabolism
Cyclopentanes - pharmacology
Exact sciences and technology
Glutamatergic system (aspartate and other excitatory aminoacids)
Glutamates - chemical synthesis
Glutamates - metabolism
Glutamates - pharmacology
Guanosine 5'-O-(3-Thiotriphosphate) - metabolism
Humans
Medical sciences
Molecular Conformation
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Organic chemistry
Pharmacology. Drug treatments
Preparations and properties
Protein Binding
Rats
Receptors, Metabotropic Glutamate - agonists
Stereoisomerism
Structure-Activity Relationship
Transfection
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Summary:An efficient method for preparing conformationally restricted cyclopentenyl-glutamate analogues in a regioselective and diastereoselective manner has been developed using a formal [3 + 2] cycloaddition reaction of dehydroamino acids. Methods for preparing optically active versions of these compounds have also been devised. Of these compounds, (S)-2 is an agonist at the mGlu5 (EC50 18 μM) and mGlu2 (EC50 45 μM) receptors.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo010864i