Synthesis and antioxidant properties of new chromone derivatives

• Published in: Bioorganic & medicinal chemistry 2009-10, Vol.17 (20), p.7218-7226
• Main Authors: Gomes, Ana, Neuwirth, Ondrej, Freitas, Marisa, Couto, Diana, Ribeiro, Daniela, Figueiredo, Andrea G.P.R., Silva, Artur M.S., Seixas, Raquel S.G.R., Pinto, Diana C.G.A., Tomé, Augusto C., Cavaleiro, José A.S., Fernandes, Eduarda, Lima, José L.F.C.
• Format: Article
• Language: English
• Subjects: 2-Styrylchromones; 3-Substituted flavones; Antioxidants - chemical synthesis; Antioxidants - pharmacology; Biological and medical sciences; Chromones - chemical synthesis; Chromones - pharmacology; General and cellular metabolism. Vitamins; Magnetic Resonance Spectroscopy; Mass Spectrometry; Medical sciences; Metal chelating activity; Methylation; Pharmacology. Drug treatments; Reactive nitrogen species; Reactive Nitrogen Species - metabolism; Reactive oxygen species; Reactive Oxygen Species - metabolism; Reducing activity; Scavenging activity
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2009.08.056

Several 2-styrylchromones and 3-substituted flavones were tested for their scavenging activity against ROS and RNS, their reducing activity and metal chelating capacity. Structure–activity relationship analysis was performed. Nowadays, the recognition of the benefits of antioxidants is eliciting an increasingly interest in the search for new molecules with improved activity. The aim of the present work was to search for improved reactive oxygen species (ROS) and reactive nitrogen species (RNS) scavengers by testing new structures of 2-styrylchromones (2-SC) and 3-substituted flavones, which were synthesised by the Baker–Venkataraman approach. The new compounds were also tested for their metal chelating capacity and reducing activity. The obtained results showed that the methylation of hydroxyl groups decreases the scavenging of ROS and RNS by 2-SC. The decrease in the scavenging activities was, generally, more evident when the methylation occurred in B-ring, except for O 2 - and 1O 2. On the other hand, the introduction of a substituent, either hydroxyl or methoxyl, in position 8 was sometimes favourable and others unfavourable to the scavenging activities, depending on the reactive species. In conclusion, the study of the antioxidant properties of the new 2-SC and flavones allowed establishing new structure–activity relationships and brought out, in some cases, pharmacophores with improved activity.