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

Research output: Contribution to journal › Article

19 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)5796-5798
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number19
DOIs
StatePublished - Oct 1 2009

Fingerprint

Bioactivity
Sodium Hypochlorite
Nitriles
Oximes
Cycloaddition
Cycloaddition Reaction
Pathogens
Oxides
Libraries
Insects
Throughput
Derivatives
Acids
1,3,4-oxadiazole
acrylic acid

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

Cite this

Milinkevich, K. A., Yoo, C. L., Sparks, T. C., Lorsbach, B. A., & Kurth, M. J. (2009). Synthesis and biological activity of 2-(4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazoles. Bioorganic and Medicinal Chemistry Letters, 19(19), 5796-5798. https://doi.org/10.1016/j.bmcl.2009.07.139

Synthesis and biological activity of 2-(4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazoles. / Milinkevich, Kristin A.; Yoo, Choong L.; Sparks, Thomas C.; Lorsbach, Beth A.; Kurth, Mark J.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 19, No. 19, 01.10.2009, p. 5796-5798.

Research output: Contribution to journal › Article

Milinkevich, KA, Yoo, CL, Sparks, TC, Lorsbach, BA & Kurth, MJ 2009, 'Synthesis and biological activity of 2-(4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazoles', Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 19, pp. 5796-5798. https://doi.org/10.1016/j.bmcl.2009.07.139
Milinkevich KA, Yoo CL, Sparks TC, Lorsbach BA, Kurth MJ. Synthesis and biological activity of 2-(4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazoles. Bioorganic and Medicinal Chemistry Letters. 2009 Oct 1;19(19):5796-5798. https://doi.org/10.1016/j.bmcl.2009.07.139
Milinkevich, Kristin A. ; Yoo, Choong L. ; Sparks, Thomas C. ; Lorsbach, Beth A. ; Kurth, Mark J. / Synthesis and biological activity of 2-(4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazoles. In: Bioorganic and Medicinal Chemistry Letters. 2009 ; Vol. 19, No. 19. pp. 5796-5798.
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