Synthesis, evaluation of antioxidant activity and crystal structure of 2,4-dimethylbenzoylhydrazones

Molecules. 2013 Sep 5;18(9):10912-29. doi: 10.3390/molecules180910912.

Abstract

2,4-Dimethylbenzoylhydrazones 1-30 were synthesized by condensation reactions of 2,4-dimethylbenzoylhydrazide with various aromatic aldehydes and characterized. The assigned structures of compounds 10, 15 and 22 were further supported by single-crystal X-ray diffraction data. The synthesized compounds were evaluated for their in vitro DPPH radical scavenging activity. They exerted varying degree of scavenging activity toward DPPH radical with IC₅₀ values between 25.6-190 µM. Compounds 1, 4, 2, 3, 7, and 6 have IC₅₀ values of 25.6, 28.1, 29.3, 29.8, 30.0 and 30.1 µM respectively, showing better activity than an n-propyl gallate standard (IC₅₀ value = 30.30 µM). For super oxide anion scavenging activity compounds 1, 2 and 3 with IC₅₀ values of 98.3, 102.6, and 105.6, respectively, also showed better activity than the n-propyl gallate standard (IC₅₀ value = 106.34 µM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biphenyl Compounds / chemistry
  • Crystallography, X-Ray
  • Free Radical Scavengers / chemical synthesis*
  • Hydrazones / chemical synthesis*
  • Picrates / chemistry
  • Superoxides / chemistry

Substances

  • Biphenyl Compounds
  • Free Radical Scavengers
  • Hydrazones
  • Picrates
  • Superoxides
  • 1,1-diphenyl-2-picrylhydrazyl