Synthesis and Antioxidant Activity of Carane and Pinane Based Sulfenimines and Sulfinimines

Chem Biodivers. 2019 Nov;16(11):e1900413. doi: 10.1002/cbdv.201900413. Epub 2019 Oct 15.

Abstract

The synthesis of sulfenimines and sulfinimines has been carried out with 10-hydroxyisocamphylthiol. The configuration of the compounds has been deduced by methods of NMR, DFT calculations and X-ray diffraction analysis. The cytotoxic, antioxidant and membrane-protective activity of the synthesized compounds as well as of the previously obtained sulfenimines and sulfinimines based on 4-caranethiol have been determined.

Keywords: antioxidant; cytotoxic activity; membrane-protective activity; monoterpenoids; red blood cells; sulfenimines; sulfinimines.

MeSH terms

  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Bicyclic Monoterpenes / chemical synthesis
  • Bicyclic Monoterpenes / chemistry
  • Bicyclic Monoterpenes / pharmacology*
  • Density Functional Theory
  • Dose-Response Relationship, Drug
  • Erythrocytes / drug effects
  • Humans
  • Imines / chemical synthesis
  • Imines / chemistry
  • Imines / pharmacology*
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Antioxidants
  • Bicyclic Monoterpenes
  • Imines
  • pinane
  • carane