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

GUADALUPE FIRPO; MARIA DOS R. MENDES DE BRITO ; MARCELA C. RODRÍGUEZ ; FERENC FÜLÖP ; MARÍA L. RAMÍREZ ; ANA P. S. CORREIA LIMA E SILVA ; GUSTAVO A. ARGÜELLO ; WALTER J. PELÁEZ; MARTÍN S. FAILLACE ; JESSICA PEREIRA COSTA; ZSOLT SZAKONYI

Antioxidants

MDPI AG

Lugar: Basel; Año: 2019 vol. 8 p. 1 - 14

Artículo Aceptado con Correcciones MenoresAbstract: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.