Synthesis and in vitro antioxidant activity evaluation of 3-carboxycoumarin derivatives and QSAR study of their DPPH• radical scavenging activity

Molecules. 2012 Dec 13;17(12):14882-98. doi: 10.3390/molecules171214882.


The in vitro antioxidant activities of eight 3-carboxycoumarin derivatives were assayed by the quantitative 1,1-diphenyl-2-picrylhydrazil (DPPH•) radical scavenging activity method. 3-Acetyl-6-hydroxy-2H-1-benzopyran-2-one (C1) and ethyl 6-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate (C2) presented the best radical-scavenging activity. A quantitative structure-activity relationship (QSAR) study was performed and correlated with the experimental DPPH• scavenging data. We used structural, geometrical, topological and quantum-chemical descriptors selected with Genetic Algorithms in order to determine which of these parameters are responsible of the observed DPPH• radical scavenging activity. We constructed a back propagation neural network with the hydrophilic factor (Hy) descriptor to generate an adequate architecture of neurons for the system description. The mathematical model showed a multiple determination coefficient of 0.9196 and a root mean squared error of 0.0851. Our results shows that the presence of hydroxyl groups on the ring structure of 3-carboxy-coumarins are correlated with the observed DPPH• radical scavenging activity effects.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Algorithms
  • Benzopyrans / chemical synthesis
  • Benzopyrans / pharmacology
  • Biphenyl Compounds / chemistry
  • Computational Biology
  • Coumarins / chemical synthesis
  • Coumarins / chemistry
  • Coumarins / pharmacology*
  • Free Radical Scavengers / chemical synthesis*
  • Free Radical Scavengers / pharmacology*
  • Models, Theoretical
  • Picrates / chemistry
  • Quantitative Structure-Activity Relationship


  • 3-acetyl-6-hydroxy-2H-1-benzopyran-2-one
  • 6-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate
  • Benzopyrans
  • Biphenyl Compounds
  • Coumarins
  • Free Radical Scavengers
  • Picrates
  • 1,1-diphenyl-2-picrylhydrazyl