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Title: Synthesis and in vitro antiproliferative activity of flavone and 6-hydroxyflavone oxime ethers derivatives
Authors: Díaz, John E.
Martinez, Diana C.
López, Lina V.
Mendez, Gina M.
Vera, Ricardo
Loaiza, Alix E.
Issue Date: 2018
Citation: Díaz, J. E., Martinez, D. C., López, L. V., Mendez, G. M., Vera, R., & Loaiza, A. E. (2018). Synthesis and in vitro antiproliferative activity of flavone and 6-hydroxyflavone oxime ethers derivatives. Journal of the Brazilian Chemical Society, 29(1), 177-184. doi:10.21577/0103-5053.20170128
Series/Report no.: Journal of the Brazilian Chemical Society;Vol.29, No.1, Ene 2018 páginas 177-184
Abstract: 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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