Synthesis and in vitro Antiproliferative Activity of Flavone and 6-Hydroxyflavone Oxime Ethers Derivatives

AUTOR(ES)

Díaz, John E., Martinez, Diana C., López, Lina V., Mendez, Gina M., Vera, Ricardo, Loaiza, Alix E.

FONTE

J. Braz. Chem. Soc.

DATA DE PUBLICAÇÃO

2018-01

RESUMO

Herein we report the synthesis of a series of O-alkyl oximes of flavone and 6-hydroxyflavone using a simple experimental protocol under solvent free conditions with yields up to 87%. Cytotoxicity of all compounds was evaluated against MDA-MB-231, PC-3, A-549 and MRC-5 cells. IC50 values for two compounds were determined to be in the range 28.7-47.8 µM against all tested cell lines. Oxime ethers derivatives showed IC50 values between 28.7 and 49.5 µM against MDA-MB-231, while the best activity was obtained for 6-hydroxyflavone with an IC50 of 3.4 µM against this cell line. Compounds containing the substituent hydroxyl at the position six of flavone system displayed the best antiproliferative activity over MDA-MB-231 cells, being necessary this group to improve the sensibility on this type of cells. The antiproliferative activity of 6-hydroxyflavone is drastically diminished when the carbonyl group of flavone is changed by an oxime ether.

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