title: Azagrevellins, Part I. Grevellin analogs with affinity to the N-methyl-D-aspartate (glycine site) receptor, a novel lead structure.
abstract: A series of piperidine-2,3,5-triones (azagrevellins) has been prepared. A new synthesis has been introduced using the rearrangement of spiroepoxides in the presence of triethyloxonium tetrafluoroborate. The binding affinity toward the N-methyl-D-aspartate (glycine site) receptor has been measured to provide a basis for more detailed structure-activity studies. Azagrevellin 18d showed the highest binding potency.
authors.affiliation: Institut für Pharmazie/Zentrum für Pharmaforschung der Universität München, Germany.
authors.forename: H
authors.initials: H
authors.lastname: Poschenrieder
authors.forename: G
authors.initials: G
authors.lastname: Höfner
authors.forename: H D
authors.initials: HD
authors.lastname: Stachel
mesh_terms: D000818:Animals; D001667:Binding, Competitive; D001921:Brain / Q000201:enzymology; D018691:Excitatory Amino Acid Antagonists / Q000378:metabolism; D007211:Indoles / Q000378:metabolism; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D018009:Receptors, Glycine / Q000037:antagonists & inhibitors / Q000378:metabolism*; D016194:Receptors, N-Methyl-D-Aspartate / Q000037:antagonists & inhibitors / Q000378:metabolism; D013329:Structure-Activity Relationship; D013552:Swine
chemical_list: D018691:Excitatory Amino Acid Antagonists; D007211:Indoles; D007659:Ketones; C101788:MDL 105519; D010880:Piperidines; D018009:Receptors, Glycine; D016194:Receptors, N-Methyl-D-Aspartate