Synthesis and biological activity of 2-(4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazoles

Kristin A. Milinkevich; Choong L. Yoo; Thomas C. Sparks; Beth A. Lorsbach; Mark J. Kurth

doi:10.1016/j.bmcl.2009.07.139

Synthesis and biological activity of 2-(4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazoles

Kristin A. Milinkevich, Choong L. Yoo, Thomas C. Sparks, Beth A. Lorsbach, Mark J. Kurth

Chemistry

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

Acid hydrazides were coupled with acrylic acid derivatives and cyclodehydration gave 1,3,4-oxadiazoles. Lastly, in-situ nitrile oxide formation from aryl oximes treated with sodium hypochlorite, and subsequent 1,3-dipolar cycloaddition to the exomethylene moiety delivered 2-(4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazoles. This library was evaluated in a high-throughput screen at Dow AgroSciences. Several compounds were active against fungal pathogens and pest insects.

Original language	English (US)
Pages (from-to)	5796-5798
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	19
DOIs	https://doi.org/10.1016/j.bmcl.2009.07.139
State	Published - Oct 1 2009

Keywords

1,3,4-Oxadiazole
Diheterocylce
Insecticidal activity
Isoxazoline
Small molecule library

ASJC Scopus subject areas

Pharmaceutical Science
Drug Discovery
Organic Chemistry
Molecular Medicine
Molecular Biology
Clinical Biochemistry
Biochemistry

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10.1016/j.bmcl.2009.07.139

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title = "Synthesis and biological activity of 2-(4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazoles",

abstract = "Acid hydrazides were coupled with acrylic acid derivatives and cyclodehydration gave 1,3,4-oxadiazoles. Lastly, in-situ nitrile oxide formation from aryl oximes treated with sodium hypochlorite, and subsequent 1,3-dipolar cycloaddition to the exomethylene moiety delivered 2-(4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazoles. This library was evaluated in a high-throughput screen at Dow AgroSciences. Several compounds were active against fungal pathogens and pest insects.",

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AU - Milinkevich, Kristin A.

AU - Yoo, Choong L.

AU - Sparks, Thomas C.

AU - Lorsbach, Beth A.

AU - Kurth, Mark J.

PY - 2009/10/1

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KW - 1,3,4-Oxadiazole

KW - Diheterocylce

KW - Insecticidal activity

KW - Isoxazoline

KW - Small molecule library

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Synthesis and biological activity of 2-(4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazoles

Abstract

Keywords

ASJC Scopus subject areas

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