Synthesis Of 7-Hydroxy-4'-Methoxyflavanone And 7-Hydroxy-4'-Methoxyflavone As A Candidate Anticancer Against Cervical (Hela) Cancer Cell And Colon (Widr) Cancer Cell By In Vitro

摘要

The compound 7-hydroxy-4'-methoxyflavanone and 7-hydroxy-4'-methoxyflavone have been synthesized through cyclization reaction of 2', 4'-dihydroxy-4-methoxychalcone (1,3-diphenyl-2-propene-1-one). The 2', 4'-dihydroxy-4-methoxychalcone were synthesized through Claisen-Schmidt condensation from 2,4-dihydroxyacetophenone and 4-methoxybenzaldehyde (anisaldehyde) in aqueous KOH as a catalyst in ethanol. The 7-hydroxy-4'-methoxyflavanone has been synthesized through cyclization reaction of 2', 4'-dihydroxy-4-methoxychalcone by Oxa-Michael addition reaction with sulfuric acid as a catalyst in ethanol. The 7-hydroxy-4'-methoxyflavone has been synthesized through oxidative cyclization reaction of 2', 4'-dihydroxy-4-methoxychalcone using I_2 in DMSO as a catalyst with a mole ratio (1: 1) mol. All these producets were characterized by FT-IR, GC-MS, and ~1H-NMR and ~(13)C-NMR spectrometer. Both of these compounds were tested citotoxycity activity as an anticancer against cervical and colon cancer cells (HeLa and WiDr cell lines) using MTT assay in vitro. Dose series given test solution concentration on HeLa and WiDr cells starting from 0,78; 1,56; 3,12; 6,25; 12,50; 25; 50 and 100 μg/mL with a long incubation treatment for 24 hours. The results study showed that the 7-hydroxy-4'-methoxyflavanone as bright yellow crystals with a melting point 172-174°C and a yield of 56.67% and the 7-hydroxy-4'-methoxyflavone as bright yellow crystals with a yield of 88, 31%, and a melting point of 263-265°C. The test results cytotoxic 7-hydroxy-4-methoxyflavone showed active against HeLa cells with IC_(50) value of 25.73 μg/mL and was quite active in the WiDr cells with IC_(50) value of 83.75 μg/mL. The result of the activity of 7-hydroxy-4-methoxyflavanone show active cytotoxic activity against HeLa and WiDr cell growth with IC_(50) value of 40.13 μg/mL and 37.85 μg/mL. IC_(50) value indicated that 7-hydroxy-4'-methoxyflavone and 7-hydroxy-4'-methoxyflavanone potential as inhibitors in HeLa and WiDr. cells.