A New Strategy for the Synthesis of Nonsymmetrical 3,3’-(Aryl/alkyl-methylene)bis-2-hydroxy-1,4-naphthoquinones and Their Cytotoxic Effects in PC3 Prostate Cancer Cells

• Autor(a) principal: Ribeiro,Ruan Carlos B.
• Data de Publicação: 2020
• Outros Autores: Freitas,Paula Priscilla de, Moreira,Caroline S., Moraes,Leonardo G. C. de, Moraes,Matheus G. de, Silva,Fernando de C. da, Rocha,David R., Gimba,Etel R. Pereira, Ferreira,Vitor F.
• 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=S0103-50532020000200288
• topic: 3,3’-arylmethylenes; 3,3’-alkylmethylenes; nonsymmetrical bis(2-hydroxynaphthalene-1,4-dione); lawsone; Mannich adduct; quinone methide

A novel method for the synthesis of nonsymmetrical 3,3’-(aryl/alkyl-methylene)bis-2-hydroxy-1,4-naphthoquinones was developed by using the Mannich adduct of naphthoquinone and the reaction with another moiety of 2-hydroxy-1,4-naphthoquinone. This novel method produces for the first time nonsymmetrical 3,3’-(aryl/alkyl-methylene)bis-2-hydroxy-1,4-naphthoquinones. In a preliminary study, these compounds (15c, 15f and 15h) were evaluated regarding their effect over the viability of PC3 metastatic prostate cancer cell using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays at 100 µM. Three of these compounds presented relevant cytotoxic effects at 72 h posttreatment.