title: Design and synthesis of propeller-shaped dispiroisoxazolinopiperidinochromanones.
abstract: A library of novel, propeller-shaped dispirotriheterocyclic isoxazolinopiperidinochromanones is reported. Each rigid dispirotriheterocycle was prepared in five linear steps from commercially available tert-butyl 4-oxopiperidine-1-carboxylate and various derivatives of 1-(2-hydroxyphenyl)ethanone, benzaldehyde oxime, and carboxylic acids. Computational chemistry was employed to analyze the three-dimensional geometries of these dispirotriheterocycles, as well as to generate chemoinformatic bioavailability data. X-ray crystallographic structure determination verified the regioselectivity of the nitrile oxide 1,3-dipolar cycloaddition reaction. The resulting library of compounds has been added to the National Institutes of Health repository (approximately 10 mg of each with > or =90% purity) for pilot-scale biomedical studies with bioassay data available at the National Center for Biotechnology Information PubChem database.
authors.affiliation: Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, USA.
authors.forename: Richard D
authors.initials: RD
authors.lastname: Carpenter
authors.forename: Patrick B
authors.initials: PB
authors.lastname: DeBerdt
authors.forename: Jason B
authors.initials: JB
authors.lastname: Holden
authors.forename: Kristin A
authors.initials: KA
authors.lastname: Milinkevich
authors.forename: Taewoo
authors.initials: T
authors.lastname: Min
authors.forename: Dan
authors.initials: D
authors.lastname: Willenbring
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger
authors.forename: Dean J
authors.initials: DJ
authors.lastname: Tantillo
authors.forename: Mark J
authors.initials: MJ
authors.lastname: Kurth
mesh_terms: D018360:Crystallography, X-Ray; D015195:Drug Design; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D010880:Piperidines