Synthesis and Biological Evaluation of Novel Coumarins with tert-Butyl and Terpene Substituents

Chem Biodivers. 2019 Mar;16(3):e1800317. doi: 10.1002/cbdv.201800317. Epub 2019 Feb 12.

Abstract

Coumarins with terpene and tert-butyl substituents were synthesized via Pechmann condensation reaction. New derivatives were investigated in different model system for the exhibition of antioxidant, radical scavenging and membrane-protective activities. It has been found that 4-methylcoumarin derivatives with monoterpene moieties exhibit high antioxidant activities. The most active and promising for further investigations is 5-hydroxy-6,8-diisobornyl-4-methylcoumarin, containing two isobornyl substituents on the benzopyran ring.

Keywords: Pechmann condensation; antioxidant activity; coumarin; membrane-protective activity; terpenophenol.

MeSH terms

  • Animals
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Biphenyl Compounds / antagonists & inhibitors*
  • Coumarins / chemical synthesis
  • Coumarins / chemistry
  • Coumarins / pharmacology*
  • Lipid Peroxidation / drug effects*
  • Mice
  • Molecular Structure
  • Picrates / antagonists & inhibitors*
  • Terpenes / chemistry
  • Terpenes / pharmacology*

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Coumarins
  • Picrates
  • Terpenes
  • 1,1-diphenyl-2-picrylhydrazyl