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Synthesis, antiproliferative activity in cancer cells and theoretical studies of novel 6α,7β-dihydroxyvouacapan-17β-oic acid Mannich base derivatives

2010; Elsevier BV; Volume: 18; Issue: 23 Linguagem: Inglês

10.1016/j.bmc.2010.10.015

1464-3391

Felipe P.G. Euzébio, Flávio José Leite dos Santos, Dorila Piló‐Veloso, Antônio F. C. Alcântara, Ana Lúcia Tasca Góis Ruiz, João Ernesto de Carvalho, Mary Ann Foglio, Dalton L. Ferreira‐Alves, Ângelo de Fátima,

Plant biochemistry and biosynthesis

Natural products are great prototypes for the design of new anticancer agents. The plant-derived natural product 6α,7β-dihydroxyvouacapan-17β-oic acid (1) is promising for the development of more potent antiproliferative agents against human cancer cells. Indeed, its lactone derivative 6α-hydroxyvouacapan-7β,17β-lactone (2), a non-natural furanoditerpene, exhibited higher anticancer activity than compound 1. Herein, we describe the synthesis and antiproliferative activity of six new Mannich derivatives of compound 2 against nine cancer cell lines. Overall, our results revealed that Mannich derivatives 3-8 were more potent than compound 2 in inhibiting the proliferation of cancer cells. Theoretical studies also supported our findings, revealing the nucleophilic character of furan ring as an important feature for antiproliferative activity of the studied Mannich derivatives.