Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

• Type: Article in International Scientific Journal
• Date: 2016

Authors

Proenca, C (Author) Other; Albuquerque, HMT (Author) Other; Ribeiro, D (Author) Other; Freitas, M (Author) Other; Santos, CMM (Author) Other; Silva, AMS (Author) Other; Eduarda Fernandes (Author) FFUP

Journal

Title: European Journal of Medicinal Chemistry

Vol. 115

Pages: 381-392

ISSN: 0223-5234

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 17 Citations

Scopus - 14 Citations

Other information

Authenticus ID: P-00K-B6N

DOI: 10.1016/j.ejmech.2016.03.043

Abstract (EN): 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 12