Morita-Baylis-Hillman Reaction with 7-Chloroquinoline Derivatives‑New Compounds with Potential Anticancer Activity
| Autor: | Mário L. A. A. Vasconcellos, João Paulo Gomes de Oliveira, Ruver Rodrigues Feitosa Ramalho, Silvia Maria Souza, Tayná Rodrigues Olegário, Everton da Paz Silva, Maísa Cavalcanti Coelho, Guilherme S. Caleffi, Claudio G. Lima-Junior, Boniek G. Vaz, Aleff C. Castro, Rhuan Karlos Santos Mendes, Júlia L. C. Souza, Gardenia C.G. Militão |
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| Rok vydání: | 2021 |
| Předmět: | |
| Zdroj: | Journal of the Brazilian Chemical Society, Volume: 32, Issue: 2, Pages: 347-354, Published: 01 FEB 2021 Journal of the Brazilian Chemical Society v.32 n.2 2021 Journal of the Brazilian Chemical Society Sociedade Brasileira de Química (SBQ) instacron:SBQ |
| ISSN: | 0103-5053 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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