SINTESIS DAN UJI SITOTOKSISITAS 7-HIDROKSI-4’- METOKSIISOFLAVON TERHADAP SEL KANKER KOLON WiDr; SYNTHESIS AND CYTOTOXICITY TEST OF 7-HYDROXY-4’- METHOXYISOFLAVONE AGAINST COLON WiDr CANCER CELL

MULTIAWATI, NUR, Sabirin Matsjeh

2015 | Disertasi | FMIPA

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 product’s structures were elucidated using GC-MS, FTIR, 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 ?g/mL. It was concluded that this isoflavone was not active to inhibit the growth of colon WiDr cancer cell.

Kata Kunci : 7-hydroxy-4'-methoxyisoflavone; p-anisaldehyde; anticancer colon