ABSTRACT: Synthesis and in vitro cytotoxicity test of 7-hydroxy-4'-methoxyisoflavone from p-anisaldehyde have been accomplished. This study is aimed to obtain anticancer compound from p-anisaldehyde via deoxybenzoin pathway and to know the cytotoxicity activity of synthesized compounds towards colon WiDr cancer cell. The synthesis was started by converting p-anisaldehyde into 4-methoxybenzyl carboxylic acid via reduction, bromination, nitrilisation, and hydrolysis steps. Friedel Crafts acylation of 4-methoxybenzyl carboxylic acid with resorcinol was performed using BF3-Et2O catalyst under reflux for 2 h. The final step is addition of one carbon atom and cyclization using BF3-Et2O and POCl3 in DMF. All of the products structures were elucidated using GC-MS, FT-IR, 1H- and 13C-NMR spectrometers. The cytotoxicity of 7-hydroxy-4'-metoxyisoflavone was tested in vitro towards colon WiDr cancer cell by MTT method. 4-Methoxybenzyl carboxylic acid was yielded as white solid in 89.23%. Friedel Craft acylation reaction produced 4-metoxybenzyl -2',4'-dihydroxyphenyl ketones as yellow solid in 95.41%. The cyclization step afforded 7-hydroxy-4'-methoxyiisoflavone in 87.18% yield as white solid. The cytotoxicity test of the resulted isoflavone against colon WiDr cancer cell gave an IC50 value of 370.74 µg/mL. It was concluded that this isoflavone was not active to inhibit the growth of colon WiDr cancer cell.
