New enamine derivatives of lapachol and biological activity

Abstract

A convenient synthesis of the new enamine derivatives 2-(4-morpholinyl)-3-(3-methyl-2-butenyl)-1,4-naphthalenedione, 2-(1-piperidinyl)-3-(3-methyl-2-butenyl)-1,4-naphtalenedione and 2-(1-pyrrolidinyl)-3-(3-methyl-2-butenyl)-1,4-naphthalenedione was carried out from natural 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione (lapachol) and morpholine, piperidine and pyrrolidine. The structures of the products were established mainly by NMR analysis, including 2D experiments. Biological activities of these products were evaluated against Artemia salina, Aedes aegypti and cytotoxicity using A549 human breast cells.Uma síntese conveniente dos novos derivados enamínicos 2-(4-morfolinil)-3-(3-metil-2-butenil)-1,4-naftaleno-diona, 2-(1-piperidinil)-3-(3-metil-2-butenil)-1,4-naftalenodiona e 2-(1-pirrolidinil)-3-(3-metil-2-butenil)-1,4-naftalenodiona foi conseguida de 2-hidroxi-3-(3-metil-2-butenil)-1,4-naftalenodiona (lapachol) natural e morfolina, piperidina e pirrolidina. As estruturas dos produtos foram estabelecidas principalmente pela análise de RMN, inclusive experimentos 2D. Atividades biológicas destes produtos foram avaliadas contra Artemia salina, Aedes aegypti e citotoxicidade usando células humanas A549.

Keywords

• lapachol
• derivados enamínicos
• atividades biológicas
• lapachol
• enamine derivatives
• biological activities