Antioxidants (Jun 2019)

Evaluation of the Antioxidant Activity of <i>Cis</i>/<i>Trans</i>-<i>N</i>-Phenyl-1,4,4a,5,8,8a-Hexahydro-3,1-Benzoxazin-2-Imines

  • Guadalupe Firpo,
  • María L. Ramírez,
  • Martín S. Faillace,
  • Maria dos R. Mendes de Brito,
  • Ana P. S. Correia Lima e Silva,
  • Jessica Pereira Costa,
  • Marcela C. Rodríguez,
  • Gustavo A. Argüello,
  • Zsolt Szakonyi,
  • Ferenc Fülöp,
  • Walter J. Peláez

DOI
https://doi.org/10.3390/antiox8060197
Journal volume & issue
Vol. 8, no. 6
p. 197

Abstract

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The growing interest in the chemistry of unsaturated ring-fused 1,3-heterocycles, in this particular case 1,3-oxazines, arise in part from their versatile pharmacological applications. In the present article, the evaluation of the in vitro and ex vivo antioxidant activity of two cyclohexene-fused oxazines is discussed. The in vitro antioxidant activity was evaluated by trapping the ABTS and hydroxyl radicals as well as the inhibition of the enzyme acetyl-cholinesterase and hemolysis of erythrocytes by 2,2’-Azobis(2-amidinopropane) dihydrochloride (AAPH). The results suggest that both unsaturated 1,3-oxazines are auspicious sources of biologically active compounds with good antioxidant properties. In addition, a comprehensive analysis of the interaction between these heterocycles with 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radicals, as well as the measurements of redox potential, provided evidence for a mechanism of antioxidant activity that takes place through electron transfer (ET) processes.

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