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Synthesis and Anticancer Activity of Homodimeric Morita-Baylis-Hillman Adducts Based on 3-Hydroxyindolin-2-one Core

2023; Brazilian Chemical Society; Linguagem: Inglês

10.21577/0103-5053.20230038

1678-4790

Maísa Coelho, Aleff Castro, Tayná Olegário, Rodrigo Cristiano, Boniek G. Vaz, Gabriel Franco dos Santos, Lucas Machado, Gardênia Carmen Gadelha Militão, Paulo da Silva, Mário Luiz Araújo de Almeida Vasconcellos, Cláudio Gabriel Lima-Júnior,

Ferrocene Chemistry and Applications

Cancer treatment represents one of the main scientific study targets today, mainly due to the pronounced side effects arising from chemotherapy. This study reports the synthesis, characterization, and anticancer activity of ten compounds from the Morita-Baylis-Hillman reaction. Ethylene glycol diacrylate was used as a double Michael acceptor in reactions with isatin derivatives to give homodimers of 3-hydroxyindolin-2-one core, recognized in the literature for its extensive pharmacological profile. The use of 1,4-diazabicyclo[2,2,2]octane (DABCO) as a catalyst and room temperature were the optimal conditions for the study reaction. The isolated yields were up to 63%, with most reaction times inferior to 24 h, some as fast as 15 min. The anticancer potential of the synthesized dimers was evaluated in vitro against three cancer strains, resulting in average inhibitory concentrations up to 0.72 μM. It was also found that the best performing homodimers are more active than their monomeric counterparts. Considering the promising selectivity indices observed, the preliminary results obtained here act as a basis for broader tests regarding the effectiveness of homodimeric adducts against cancer cells.