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 › peer-review

15 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

ASJC Scopus subject areas

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

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10.1021/cc700173x

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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 › peer-review

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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-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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doi = "10.1021/cc700173x",

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AU - Carpenter, Richard D.

AU - DeBerdt, Patrick B.

AU - Holden, Jason B.

AU - Milinkevich, Kristin A.

AU - Min, Taewoo

AU - Willenbring, Dan

AU - Fettinger, James C.

AU - Tantillo, Dean J.

AU - Kurth, Mark J.

PY - 2008/3

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N2 - 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.

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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Design and synthesis of propeller-shaped dispiroisoxazolinopiperidinochromanones

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