Artículo
Design, synthesis, and molecular docking study of novel quinoline-based bis-chalcones as potential antitumor agents
Insuasty, Daniel; García, Stephanie; Abonia, Rodrigo; Insuasty, Braulio; Quiroga, Jairo; Nogueras, Manuel; Cobo, Justo; Borosky, Gabriela Leonor
; Laali, Kenneth K.
Fecha de publicación:
09/2021
Editorial:
Wiley VCH Verlag
Revista:
Archiv Der Pharmazie
ISSN:
0365-6233
e-ISSN:
1521-4184
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
A novel series of quinoline-based symmetrical and unsymmetrical bis-chalcones was synthesized via a Claisen–Schmidt condensation reaction between 3-formyl-quinoline/quinolone derivatives with acetone or arylidene acetones, respectively, by using KOH/MeOH/H2O as a reaction medium. Twelve of the obtained compounds were evaluated for their in vitro cytotoxic activity against 60 different human cancer cell lines according to the National Cancer Institute protocol. Among the screened compounds, the symmetrical N-butyl bis-quinolinyl-chalcone 14g and the unsymmetrical quinolinyl-bis-chalcone 17o bearing a 7-chloro-substitution on the N-benzylquinoline moiety and 4-hydroxy-3-methoxy substituent on the phenyl ring, respectively, exhibited the highest overall cytotoxicity against the evaluated cell lines with a GI50 range of 0.16–5.45 µM, with HCT-116 (GI50 = 0.16) and HT29 (GI50 = 0.42 μM) (colon cancer) representing best-case scenarios. Notably, several GI50 values for these compounds were lower than those of the reference drugs doxorubicin and 5-FU. Docking studies performed on selected derivatives yielded very good binding energies in the active site of proteins that participate in key carcinogenic pathways.
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Articulos(INFIQC)
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Citación
Insuasty, Daniel; García, Stephanie; Abonia, Rodrigo; Insuasty, Braulio; Quiroga, Jairo; et al.; Design, synthesis, and molecular docking study of novel quinoline-based bis-chalcones as potential antitumor agents; Wiley VCH Verlag; Archiv Der Pharmazie; 354; 9; 9-2021; 1-20
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