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

Journal of the Brazilian Chemical Society

Díaz, John E.¹  Martinez, Diana C.² 

[1]Pontificia Universidad Javeriana, Bogotá, Colombia

[2]Universidad de Ciencias Aplicadas y Ambientales, Bogotá, Colombia

关键词: synthesis;    oxime ethers;    flavone;    6-hydroxyflavone;    antiproliferative activity.;   

DOI  :  10.21577/0103-5053.20170128

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

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.

【 授权许可】

CC BY