Synthesis of Isoxazolines by the Electrophilic Chalcogenation of β,γ-Unsaturated Oximes: Fishing Novel Anti-Inflammatory Agents

J Org Chem. 2019 Oct 4;84(19):12452-12462. doi: 10.1021/acs.joc.9b01754. Epub 2019 Sep 25.

Abstract

Herein, we describe a new strategy to prepare chalcogen-functionalized isoxazolines. The strategy involves the reaction of β,γ-unsaturated oximes with electrophilic selenium and tellurium species, affording 19 new selenium- and tellurium-containing isoxazolines in good yields after 1 h at room temperature. The method was efficiently extended to the synthesis of 5 new (bis)isoxazoline ditellurides. One of the prepared compounds, 3-phenyl-5-((phenylselanyl)methyl)-isoxazoline, demonstrated better anti-inflammatory and antiedematogenic effects than the reference drug Celecoxib.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / therapeutic use*
  • Croton Oil
  • Dose-Response Relationship, Drug
  • Ear
  • Edema / chemically induced
  • Edema / drug therapy*
  • Isoxazoles / chemical synthesis
  • Isoxazoles / chemistry
  • Isoxazoles / therapeutic use*
  • Male
  • Mice
  • Molecular Structure
  • Oximes / chemistry
  • Oximes / therapeutic use*

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Isoxazoles
  • Oximes
  • Croton Oil