Diastereoselective ruthenium porphyrin-catalyzed tandem nitrone formation/1,3-dipolar cycloaddition for isoxazolidines. Synthesis, in silico docking study and in vitro biological activities

Org Biomol Chem. 2012 Dec 14;10(46):9165-74. doi: 10.1039/c2ob26518d. Epub 2012 Sep 11.

Abstract

Ruthenium porphyrin catalyzes tandem nitrone formation/1,3-dipolar cycloaddition of diazo compounds, nitrosoarenes and alkenes to form isoxazolidines in good to high yields and with excellent regio-, chemo- and diastereo-selectivities. A broad substrate scope of alkenes is applicable to this protocol and various functional groups are compatible with the reaction conditions. In silico analysis and in vitro biological experiments revealed that some of the new isoxazolidines synthesized in this work could act as leukotriene A4 hydrolase inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Azo Compounds / chemistry*
  • Binding Sites
  • Catalysis
  • Coordination Complexes / chemistry
  • Cyclization
  • Cycloaddition Reaction
  • Enzyme Inhibitors / chemical synthesis*
  • Epoxide Hydrolases / antagonists & inhibitors
  • Humans
  • Isoxazoles / chemical synthesis*
  • Molecular Docking Simulation
  • Molecular Structure
  • Nitrogen Oxides / chemical synthesis*
  • Porphyrins / chemistry*
  • Protein Binding
  • Recombinant Proteins / antagonists & inhibitors
  • Ruthenium / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Azo Compounds
  • Coordination Complexes
  • Enzyme Inhibitors
  • Isoxazoles
  • Nitrogen Oxides
  • Porphyrins
  • Recombinant Proteins
  • nitrones
  • Ruthenium
  • Epoxide Hydrolases
  • leukotriene A4 hydrolase