Romanian Society of Pharmaceutical Sciences

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STUDIES ON XANTHINE DERIVATIVES (II). SYNTHESIS AND ANTIOXIDANT EFFECTS OF SOME HYDRAZONES WITH XANTHINE STRUCTURE

SANDRA CONSTANTIN1, FREDERIC BURON2, SYLVAIN ROUTIER2, LUMINIȚA CONFEDERAT1, ANDREEA TEODORA IACOB1, ANCA MIRON1, LENUȚA PROFIRE1*

1.University of Medicine and Pharmacy ”Grigore. T. Popa” Iași, Faculty of Pharmacy, Universității Street, no. 16, 700115, Iași, Romania
2.University of Orleans, CNRS, Institut de Chimie Organique et Analytique, UMR 7311, Rue de Chartres BP 6759, F-45067 Orléans, France

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A series of thirteen hydrazones with xanthine structure (derivatives of theophylline) have been synthesized and characterized in terms of physical and chemical properties. Their structure was proved using spectral methods (infrared – IR, proton nuclear magnetic resonance – 1H-NMR, carbon-13 nuclear magnetic resonance – 13C-NMR, high resolution mass spectroscopy – HRMS). The antioxidant effects of the synthesized compounds were evaluated using in vitro assays: DPPH (2,2-Diphenyl-1-picrylhydrazyl) and ABTS (2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)) radical scavenging ability and total antioxidant capacity. The results showed that the chemical modulation of theophylline was associated with improving of the antioxidant effects of the parent compound, generally. The most active compound was hydrazone c, which has 2-OH as substituent on the aromatic ring, its ABTS scavenging activity being comparable with ascorbic acid. The substitution of the aromatic ring with 3/4-OH, 4-NO2 and 4-CN was also associated with improved antioxidant effects, the corresponding derivatives having appreciable DPPH and ABTS scavenging effects and total antioxidant capacity.