Biomimetic catalysis of flavones derivatives using a synthetic porphyrin

• Autor(a) principal: Maia, Renato Ribeiro
• Data de Publicação: 2018
• Tipo de documento: Dissertação
• Idioma: eng
• Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
• Texto Completo: http://hdl.handle.net/10773/25489
• topic: Flavones; Chalcones; Biomimetic catalysis; Porphyrin; Biological activity

Since flavones present a diverse and vast list of biological activities, including antioxidant, anti-inflammatory, anticancer, antimicrobial, antiviral, antidiabetic, anti-allergic, activities or modulation of enzyme activity or metabolic pathways like the lipid metabolism, the synthesis of new flavones bearing uncommon patterns may be extremely useful. Though, these new flavone derivatives may be bioactive, one question needs to be answered, are they properly metabolized in biological systems? To answer that, biomimetic studies are a good strategy and synthetic porphyrins can be used in biomimetic oxidations. Simultaneously, these biomimetic oxidations can be a new way to obtain new flavones. In this work new flavones bearing naphthyl groups were obtained in good yields (> 60%). They were synthesised by the oxidative cyclization of the appropriated chalcone derivatives, which were obtained through a Claisen-Schmidt condensation in very good yields (> 70%). The biomimetic oxidation showed that only the 2-naphthyl moiety was oxidised, indicated that the benzochromenone scaffold is very stable. In addition, the biomimetic oxidation led to the synthesis of new flavone derivatives. One of the oxidation products was evaluated for its antioxidant and anti-cholinesterase activities, unfortunately the results showed that its activity is not significant. The characterization of all synthesised compounds was made by nuclear magnetic resonance (NMR) spectroscopic studies, including 1H and 13C, and two-dimensional heteronuclear correlated spectroscopy (HSQC and HMBC)