Natural Organic Acid as Green Catalyst for Xanthenones Synthesis: Methodology, Mechanism and Calcium Channel Blocking Activity

• Autor(a) principal: Terra,Bruna S.
• Data de Publicação: 2017
• Outros Autores: Osorio,Aura M. B., Oliveira,Aline de, Santos,Rebeca P. M., Mouro,Andressa P., Araújo,Natália F. de, Silva,Cameron C. da, Martins,Felipe T., Vieira,Luciene B., Bonaventura,Daniella, Abreu,Heitor A. de, Alcântara,Antonio F. C., Fátima,Ângelo de
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017001202313
• topic: xanthenones; natural organic acid; theoretical calculations; calcium channels blockers

Xanthenones were synthesized via one-pot tricomponent reaction, under solvent-free conditions, using aldehydes, phenolic and cyclic 1,3-dicarbonyl compounds. Natural organic acids (NOAs), compounds present in many living metabolisms, were used as potential green catalysts. NOA are considered to be more eco-friendly and user-friendly alternative to traditional methodologies. Optimization studies showed that oxalic acid was the best NOA catalyst for such reaction furnishing the xanthenones with up to 93% of yield. Theoretical calculations were performed to evaluate this reaction mechanism and regioselectivity. The results showed that the regiospecificity of this three-component reaction is kinetically and thermodynamically controlled by the addition of β-naphthol C2, instead of C10, to the aldehyde. Our results also disclosed two xanthenones as novel calcium channels blockers. Eco-friendly reaction conditions, easy workup procedure, short reaction times and good yields are some of the advantages of our methodology.