Design and synthesis of propeller-shaped dispiroisoxazolinopiperidinochromanones

Richard D. Carpenter, Patrick B. DeBerdt, Jason B. Holden, Kristin A. Milinkevich, Taewoo Min, Dan Willenbring, James C. Fettinger, Dean J. Tantillo, Mark J. Kurth

Research output: Contribution to journalArticle

14 Scopus citations

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-l-carboxylate and various derivatives of l-(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 (∼10 mg of each with ≥90% purity) for pilot-scale biomedical studies with bioassay data available at the National Center for Biotechnology Information PubChem database.

Original languageEnglish (US)
Pages (from-to)225-229
Number of pages5
JournalJournal of Combinatorial Chemistry
Volume10
Issue number2
DOIs
StatePublished - Mar 2008

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Discrete Mathematics and Combinatorics

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    Carpenter, R. D., DeBerdt, P. B., Holden, J. B., Milinkevich, K. A., Min, T., Willenbring, D., Fettinger, J. C., Tantillo, D. J., & Kurth, M. J. (2008). Design and synthesis of propeller-shaped dispiroisoxazolinopiperidinochromanones. Journal of Combinatorial Chemistry, 10(2), 225-229. https://doi.org/10.1021/cc700173x