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Morita-Baylis-Hillman Reaction with 7-Chloroquinoline Derivatives‑New Compounds with Potential Anticancer Activity

2020; Brazilian Chemical Society; Linguagem: Inglês

10.21577/0103-5053.20200185

1678-4790

João Paulo Gomes de Oliveira, Guilherme S. Caleffi, Everton P. Silva, Maísa Coelho, Aleff Castro, Rhuan Karlos Santos Mendes, Tayná Olegário, Cláudio Gabriel Lima-Júnior, Mário Luiz Araújo de Almeida Vasconcellos, Júlia L. C. Souza, Sílvia Silva de Souza, Gardênia Carmen Gadelha Militão, Boniek G. Vaz, Ruver Rodrigues Feitosa Ramalho,

Metal complexes synthesis and properties

Morita-Baylis-Hillman adducts (MBHA) is a class of polyfunctional molecules that has been standing out due to their versatility and expressive biological activities.Therefore, this paper describes the synthesis and antiproliferative activity of some new MBHA/7-choroquinoline hybrids.The Michael acceptors were obtained starting from 4,7-dichloroquinoline which were submitted to the Morita-Baylis-Hillman reaction with ortho, meta and para-nitrobenzaldehyde.The in vitro screening of the synthetized MBHA against NCI-H292, HCT-116 and MCF-7 cancer cells suggests the influence of the spacer chain in its inhibition potential.The 50% inhibitory concentration (IC 50 ) obtained in the antiproliferative assay using MCF-7, HCT-116, HL-60 and NCI-H292 cancer cells indicate expressive cytotoxic potential of the adducts containing nitro group in the ortho position, with IC 50 of 4.60 µmol L -1 .MBHA/7-choroquinoline hybrids were more active than MBHA described in literature, indicating the improvement of the cytotoxic effect due to 7-chloroquinoline moiety in the molecular structure, with maximum selectivity index values of 11.89.