Journal
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume 115, Issue -, Pages 381-392Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2016.03.043
Keywords
Chromones; Xanthones; Reactive oxygen species; Reactive nitrogen species; Antioxidant activity
Categories
Funding
- FCT [SFRH/BD/86277/2012, SFRH/BPD/76909/2011]
- FSE
- national funds of MCTES
- Fundação para a Ciência e a Tecnologia [SFRH/BD/86277/2012] Funding Source: FCT
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Chromones and xanthones are oxygen-containing heterocyclic compounds acknowledged by their antioxidant properties. In an effort to develop novel agents with improved activity, a series of compounds belonging to these chemical classes were prepared. Their syntheses involve the condensation of appropriate 2-methyl-4H-chromen-4-ones, obtained via Baker-Venkataraman rearrangement, with (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde to provide the corresponding 2-[(1E,3E)-4-(3,4-dimethoxyphenyl)buta-1,3-dien-1-y1]-4H-chromen-4-ones. Subsequent electrocyclization and oxidation of these compounds led to the synthesis of 1-aryl-9H-xanthen-9-ones. After cleavage of the protecting groups, hydroxylated chromones and xanthones were assessed as scavenging agents against both reactive oxygen species (ROS) [superoxide radical (On, hydrogen peroxide (H2O2), hypochlorous acid (HOG), singlet oxygen (O-1(2)), and peroxyl radical (ROW)] and reactive nitrogen species (RNS) [nitric oxide ((NO)-N-center dot) and peroxynitrite anion (ONOO-)]. Generally, all the tested new hydroxylated chromones and xanthones exhibited scavenger effects dependent on the concentration, with IC50 values found in the micromolar range. Some of them were shown to have improved scavenging activity when compared with previously reported analogues, allowing the inference of preliminary conclusions on the structure activity relationship. (C) 2016 Elsevier Masson SAS. All rights reserved.
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