Parallel synthesis of bis-heterocyclic isoxazolylmethyl- And isoxazolinylmethylpyrazoles

Liping Meng, Beth A. Lorsbach, Thomas C. Sparks, James C. Fettinger, Mark J. Kurth

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The solution-phase parallel synthesis of a 136-member library of isoxazol(in)e-CH2-pyrazoles is described, X-ray crystallographic structure determination verified the regioselectivities of the N-alkylation and nitrile oxide 1,3-dipolar cycloaddition steps. The construction of these pharmaceutically relevant heterocycles on solid support under microwave irradiation is also demonstrated. The resulting library of drug-like 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. A subset of these compounds has been broadly screened by Dow AgroSciences for herbicidal, fungicidal, and insecticidal activity.

Original languageEnglish (US)
Pages (from-to)129-136
Number of pages8
JournalJournal of Combinatorial Chemistry
Volume12
Issue number1
DOIs
StatePublished - Jan 11 2010

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Pyrazoles
Regioselectivity
Nitriles
Microwave irradiation
Cycloaddition
Bioassay
Alkylation
Biotechnology
Oxides
Health
X rays
Pharmaceutical Preparations
azastene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Parallel synthesis of bis-heterocyclic isoxazolylmethyl- And isoxazolinylmethylpyrazoles. / Meng, Liping; Lorsbach, Beth A.; Sparks, Thomas C.; Fettinger, James C.; Kurth, Mark J.

In: Journal of Combinatorial Chemistry, Vol. 12, No. 1, 11.01.2010, p. 129-136.

Research output: Contribution to journalArticle

Meng, Liping ; Lorsbach, Beth A. ; Sparks, Thomas C. ; Fettinger, James C. ; Kurth, Mark J. / Parallel synthesis of bis-heterocyclic isoxazolylmethyl- And isoxazolinylmethylpyrazoles. In: Journal of Combinatorial Chemistry. 2010 ; Vol. 12, No. 1. pp. 129-136.
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