Design and synthesis of propeller-shaped dispiroisoxazolinopiperidinochromanones

被引：15

作者：

Carpenter, Richard D. ^{[1
]}

DeBerdt, Patrick B. ^{[1
]}

Holden, Jason B. ^{[1
]}

Milinkevich, Kristin A. ^{[1
]}

Min, Taewoo ^{[1
]}

Willenbring, Dan ^{[1
]}

Fettinger, James C. ^{[1
]}

Tantillo, Dean J. ^{[1
]}

Kurth, Mark J. ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2008年 / 10卷 / 02期

关键词：

D O I：

10.1021/cc700173x

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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 (similar to 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.

引用

页码：225 / 229

页数：5

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