Morita-Baylis-Hillman reaction with 7-chloroquinoline derivatives-new compounds with potential anticancer activity
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Data
2021
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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.
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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.