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

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.

Keywords:
antiproliferative activity; Morita-Baylis-Hillman adducts; 4; 7-dichloroquinoline; nitrobenzaldehydes; C-C bond