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 | |
| State | Published - Mar 2008 |
Fingerprint
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry
- Chemistry(all)
- Discrete Mathematics and Combinatorics
Cite this
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
}
TY - JOUR
T1 - Design and synthesis of propeller-shaped dispiroisoxazolinopiperidinochromanones
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
Y1 - 2008/3
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.
UR - http://www.scopus.com/inward/record.url?scp=42449085437&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=42449085437&partnerID=8YFLogxK
U2 - 10.1021/cc700173x
DO - 10.1021/cc700173x
M3 - Article
C2 - 18232646
AN - SCOPUS:42449085437
VL - 10
SP - 225
EP - 229
JO - ACS Combinatorial Science
JF - ACS Combinatorial Science
SN - 2156-8952
IS - 2
ER -