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

doi:10.1021/cc700173x

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

Chemistry

Research output: Contribution to journal › Article

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 language	English (US)
Pages (from-to)	225-229
Number of pages	5
Journal	Journal of Combinatorial Chemistry
Volume	10
Issue number	2
DOIs	https://doi.org/10.1021/cc700173x
State	Published - Mar 2008

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ASJC Scopus subject areas

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

Cite this

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

Design and synthesis of propeller-shaped dispiroisoxazolinopiperidinochromanones. / Carpenter, Richard D.; DeBerdt, Patrick B.; Holden, Jason B.; Milinkevich, Kristin A.; Min, Taewoo; Willenbring, Dan; Fettinger, James C.; Tantillo, Dean J.; Kurth, Mark J.

In: Journal of Combinatorial Chemistry, Vol. 10, No. 2, 03.2008, p. 225-229.

Research output: Contribution to journal › Article

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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.",

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

year = "2008",

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AU - Milinkevich, Kristin A.

AU - Min, Taewoo

AU - Willenbring, Dan

AU - Fettinger, James C.

AU - Tantillo, Dean J.

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AB - 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.

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Access to Document

10.1021/cc700173x