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, Z. Szakonyi, F. Fülöp, Walter J. Peláez

Research output: Article

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 - jún. 1 2019

Fingerprint

Imines
Oxazines
Antioxidants
Sulfonic Acids
Cholinesterases
Hemolysis
Hydroxyl Radical
Oxidation-Reduction
Erythrocytes
Pharmacology
Electrons
Enzymes
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
oxazine 1
In Vitro Techniques

ASJC Scopus subject areas

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

Cite this

Firpo, G., Ramírez, M. L., Faillace, M. S., de Brito, M. D. R. M., E Silva, A. P. S. C. L., Costa, J. P., ... 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

Evaluation of the antioxidant activity of cis/trans-N-phenyl-1,4,4a,5,8,8a-hexahydro-3, 1-benzoxazin-2-imines. / Firpo, Guadalupe; Ramírez, María L.; Faillace, Martín S.; de Brito, Maria Dos R.Mendes; E Silva, Ana P.S.Correia Lima; Costa, Jessica Pereira; Rodríguez, Marcela C.; Argüello, Gustavo A.; Szakonyi, Z.; Fülöp, F.; Peláez, Walter J.

In: Antioxidants, Vol. 8, No. 6, 197, 01.06.2019.

Research output: Article

Firpo, G, Ramírez, ML, Faillace, MS, de Brito, MDRM, E Silva, APSCL, Costa, JP, Rodríguez, MC, Argüello, GA, Szakonyi, Z, Fülöp, F & Peláez, WJ 2019, 'Evaluation of the antioxidant activity of cis/trans-N-phenyl-1,4,4a,5,8,8a-hexahydro-3, 1-benzoxazin-2-imines', Antioxidants, vol. 8, no. 6, 197. https://doi.org/10.3390/antiox8060197
Firpo G, Ramírez ML, Faillace MS, de Brito MDRM, E Silva APSCL, Costa JP et al. Evaluation of the antioxidant activity of cis/trans-N-phenyl-1,4,4a,5,8,8a-hexahydro-3, 1-benzoxazin-2-imines. Antioxidants. 2019 jún. 1;8(6). 197. https://doi.org/10.3390/antiox8060197
Firpo, Guadalupe ; Ramírez, María L. ; Faillace, Martín S. ; de Brito, Maria Dos R.Mendes ; E Silva, Ana P.S.Correia Lima ; Costa, Jessica Pereira ; Rodríguez, Marcela C. ; Argüello, Gustavo A. ; Szakonyi, Z. ; Fülöp, F. ; Peláez, Walter J. / Evaluation of the antioxidant activity of cis/trans-N-phenyl-1,4,4a,5,8,8a-hexahydro-3, 1-benzoxazin-2-imines. In: Antioxidants. 2019 ; Vol. 8, No. 6.
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