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

Terra, Bruna S., 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

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

AUTOR(ES)

Terra, Bruna S., 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

FONTE

J. Braz. Chem. Soc.

DATA DE PUBLICAÇÃO

2017-12

RESUMO

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.