Parallel synthesis of bis-heterocyclic isoxazolylmethyl- And isoxazolinylmethylpyrazoles

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

doi:10.1021/cc900133k

Parallel synthesis of bis-heterocyclic isoxazolylmethyl- And isoxazolinylmethylpyrazoles

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

Chemistry

Research output: Contribution to journal › Article

17 Scopus citations

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 language	English (US)
Pages (from-to)	129-136
Number of pages	8
Journal	Journal of Combinatorial Chemistry
Volume	12
Issue number	1
DOIs	https://doi.org/10.1021/cc900133k
State	Published - Jan 11 2010

ASJC Scopus subject areas

Chemistry(all)

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10.1021/cc900133k

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Meng, L., Lorsbach, B. A., Sparks, T. C., Fettinger, J. C., & Kurth, M. J. (2010). Parallel synthesis of bis-heterocyclic isoxazolylmethyl- And isoxazolinylmethylpyrazoles. Journal of Combinatorial Chemistry, 12(1), 129-136. https://doi.org/10.1021/cc900133k

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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.",

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