title: Synthesis and biological activities of conformationally restricted cyclopentenyl-glutamate analogues.
abstract: 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 (EC(50) 18 microM) and mGlu2 (EC(50) 45 microM) receptors.
authors.affiliation: Department of Chemistry, University of Wollongong, Wollongong, NSW, 2522, Australia.
authors.forename: Alison T
authors.initials: AT
authors.lastname: Ung
authors.forename: Karl
authors.initials: K
authors.lastname: Schafer
authors.forename: Karl B
authors.initials: KB
authors.lastname: Lindsay
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Pyne
authors.forename: Kitti
authors.initials: K
authors.lastname: Amornraksa
authors.forename: Ria
authors.initials: R
authors.lastname: Wouters
authors.forename: Ilse
authors.initials: I
authors.lastname: Van der Linden
authors.forename: Ilse
authors.initials: I
authors.lastname: Biesmans
authors.forename: Anne S J
authors.initials: AS
authors.lastname: Lesage
authors.forename: Brian W
authors.initials: BW
authors.lastname: Skelton
authors.forename: Allan H
authors.initials: AH
authors.lastname: White
mesh_terms: D000818:Animals; D016466:CHO Cells; D020013:Calcium Signaling / Q000187:drug effects; D006224:Cricetinae; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D005971:Glutamates / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D016244:Guanosine 5'-O-(3-Thiotriphosphate) / Q000378:metabolism; D006801:Humans; D008968:Molecular Conformation; D011485:Protein Binding; D051381:Rats; D018094:Receptors, Metabotropic Glutamate / Q000819:agonists*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014162:Transfection
chemical_list: D003517:Cyclopentanes; D005971:Glutamates; D018094:Receptors, Metabotropic Glutamate; D016244:Guanosine 5'-O-(3-Thiotriphosphate)