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

• Autor(a) principal: Oliveira,João Paulo G.
• Data de Publicação: 2021
• Outros Autores: Caleffi,Guilherme S., Silva,Everton P., Coelho,Maísa C., Castro,Aleff C., Mendes,Rhuan K. S., Olegário,Tayná R., Lima-Junior,Claudio G., Vasconcellos,Mario L. A. A., Souza,Júlia L. C., Souza,Sílvia M., Militão,Gardênia C. G., Vaz,Boniek G., Ramalho,Ruver R. F.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000200347
• topic: antiproliferative activity; Morita-Baylis-Hillman adducts; 4; 7-dichloroquinoline; nitrobenzaldehydes; C-C bond

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.