SYNTHESIS AND cytotoxicity assay 7,8-dihydroxy-4'-METOKSIISOFLAVON AGAINST CERVICAL CANCER CELLS AND KOLON WiDr HeLa BY IN VITRO
ABSTRACT: Synthesis of 7,8-dihydroxy-4'-methoxyisoflavone from starting material p-anisaldehyde has been done by deoxybenzoin pathways. The synthesis was started by converting p-anisaldehyde via several steps of reaction, i.e alcohol reduction, bromination, nitrilisation and hydrolysis in alkaline condition to give 4-methoxybenzyl carboxylic acid. The compound of 2,3,4-trihydroxyphenyl-4'-methoxybenzyl ketone (deoxybenzoin) was obtained from Friedel-Crafts condensation reaction between 4-methoxybenzyl carboxylic acid, pyrogallol and BF3·Et2O. The final product, 7,8-dihydroxy-4'-methoxyisoflavone, was resulted from reaction between deoxybenzoin and BF3·Et2O/DMF/POCl3 reagents, as the reagents for addition of one carbon atom and cyclization process. The structures of all products were analyzed using FTIR, GC-MS, 1H- and 13C-NMR spectrometers. The cytotoxicity of 7,8-dihydroxy-4'-methoxyisoflavone was tested in vitro against HeLa cervical and WiDr colon cancer cells with MTT method. The results showed that 4-methoxybenzyl carboxylic acid, 2,3,4-trihydroxyphenyl-4'-methoxybenzyl ketone and 7,8-dihydroxy-4'-methoxy isoflavone were yielded in 83, 93 and 88%, respectively. The cytotoxicity test indicated that 7,8-dihydroxy-4'-methoxyisoflavone had a moderate activity for inhibiting the growth of HeLa cervical and WiDr colon cancer cells with IC50 values 37,07 and 52,36 µg/mL, respectively.
