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

• Autor(a) principal: Díaz,John E.
• Data de Publicação: 2018
• Outros Autores: Martinez,Diana C., López,Lina V., Mendez,Gina M., Vera,Ricardo, Loaiza,Alix E.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100177
• topic: synthesis; oxime ethers; flavone; 6-hydroxyflavone; antiproliferative activity

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.