Morita-Baylis-Hillman reaction with 7-chloroquinoline derivatives-new compounds with potential anticancer activity

Resumo

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 (IC50) 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 IC50 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.

Descrição

Palavras-chave

Antiproliferative activity, Morita-Baylis-Hillman adducts, 4,7-dichloroquinoline, Nitrobenzaldehydes, C-C bond

Citação

OLIVEIRA, João Paulo G. et al. Morita-Baylis-Hillman reaction with 7-chloroquinoline derivatives-new compounds with potential anticancer activity. Journal of the Brazilian Chemical Society, Campinas, v. 32, n. 2, p. 347-354, 2021. DOI: 10.21577/0103-5053.20200185. Disponível em: https://www.scielo.br/j/jbchs/a/vrthDwFDVWR5RLjb8BQyyYD/?lang=en#. Acesso em: 10 ago. 2023.