Síntese e avaliação antitumoral de novos alquil-catecóis derivados da vanilina e piperonal

Abstract

Phenolic lipids are secondary metabolites produced by plants, animals, fungi, and bacteria, characterized as compounds with an alkyl side chain linked to a phenol or to a phenolic derivative. Among the phenolic lipids that have drawn attention due to their biological potential, the alkyl resorcinols stands out, which have a resorcinol-like aromatic ring constructed by the polyketide biosynthetic pathway. Recently, the NEQUIMA/UFAM research group have isolated a new glycosylated alkyl resorcinol, AR-1, which biological properties was not investigated yet. Inspired by the AR-1 structure, we aimed to synthesize a new group of alkyl resorcinols derived from vanillin and piperonal, aiming to explore possible biological activities associated with the new products. To do so, we planned to use low-cost materials and classic procedures, as the Grignard reaction, in addition to the protection/deprotection protocols of aromatic hydroxyls. We were able to deprotect successfully the methoxyl group from vanillin and synthesized the protocatechuic aldehyde, but the subsequent protection of the hydroxyls with more flexible protecting groups was not possible. Moreover, the Grignard reaction on vanillin and protocatechuic aldehyde was unsuccessful as well. On the other hand, we were able to synthesize a homologous series of seven piperonal-derived alkyl catechols with progressive increase of the alkyl side chain, which will be investigated by our research group for biological activities.