Evaluation of the antioxidant activity of cis/trans-N-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

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3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Article number197
JournalAntioxidants
Volume8
Issue number6
DOIs
Publication statusPublished - Jun 2019

Keywords

  • Antioxidant activity
  • Antiradical power
  • ET mechanism
  • Unsaturated-fused 1,3-oxazines

ASJC Scopus subject areas

  • Biochemistry
  • Physiology
  • Molecular Biology
  • Clinical Biochemistry
  • Cell Biology

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    Firpo, G., Ramírez, M. L., Faillace, M. S., de Brito, M. D. R. M., E Silva, A. P. S. C. L., Costa, J. P., Rodríguez, M. C., Argüello, G. A., Szakonyi, Z., Fülöp, F., & Peláez, W. J. (2019). Evaluation of the antioxidant activity of cis/trans-N-phenyl-1,4,4a,5,8,8a-hexahydro-3, 1-benzoxazin-2-imines. Antioxidants, 8(6), [197]. https://doi.org/10.3390/antiox8060197