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

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