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

1
INFIQC-CONICET. Departamento de Físicoquímica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, X5000HUA Córdoba, Argentina
2
Department of Pharmaceutical Chemistry, Faculty of Facid Wyden, Federal University of Piauí, Teresina, PI. CEP 64.052-410, Brazil
3
Department of Pharmaceutical Chemistry, Faculty of Nursing, Federal University of Piauí, Teresina, PI. CEP 64.049-550, Brazil
4
Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös utca 6, Hungary
*
Authors to whom correspondence should be addressed.
Antioxidants 2019, 8(6), 197; https://doi.org/10.3390/antiox8060197
Received: 1 May 2019 / Revised: 12 June 2019 / Accepted: 21 June 2019 / Published: 25 June 2019
(This article belongs to the Special Issue The Chemistry of Antioxidant Activity)
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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. View Full-Text
Keywords: antioxidant activity; unsaturated-fused 1,3-oxazines; ET mechanism; antiradical power antioxidant activity; unsaturated-fused 1,3-oxazines; ET mechanism; antiradical power
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Firpo, G.; Ramírez, M.L.; Faillace, M.S.; de Brito, M.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. Evaluation of the Antioxidant Activity of Cis/Trans-N-Phenyl-1,4,4a,5,8,8a-Hexahydro-3,1-Benzoxazin-2-Imines. Antioxidants 2019, 8, 197.

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