Adições de Michael assimétricas na obtenção de naftoquinonas com potencial antitumoral

Abstract

In this study the efficiency of organocatalysts derived from Cinchona alkaloid in Michael asymmetric reactions was evaluated. 2-Hydroxy-1,4-naphthoquinone was selected as Michael donor in reactions involving -bromonitroalkenes as Michael acceptors. Assays were carried out to obtain asymmetric polysubstituted naphthofuranquinones which resulted in the formation of products with a high degree of purity (96% enantiomeric excess). The use of an organocatalyst containing a squaramide unit in its structure was identified as the best. In the course of the work, nine substances from Michael addition were synthesized without the use of chiral organocatalysts and six derivatives are unpublished in the literature. The synthesized substances were evaluated against normal and tumor cell lines, highlighting the antitumor potential of the new quinones described herein.