Sintesis Turunan Kalkon dari 3-asetilkumarin dan Uji Aktivitasnya Secara IN VITRO Sebagai Kandidat Antikanker

Ahmad Rozy Akhsan Robbani, Prof. Dra. Tutik Dwi Wahyuningsih, M.Si., Ph.D.; Prof. Dr. Chairil Anwar

2025 | Skripsi | KIMIA

Telah dilakukan sintesis senyawa turunan kalkon berbasis 3-asetilkumarin dan uji aktivitasnya terhadap sel kanker. Senyawa turunan kalkon 1 dan 2 disintesis melalui reaksi kondensasi Claisen-Schmidt antara 3-asetilkumarin dengan 2-metoksibenzaldehida dan 3-metoksibenzaldehida dalam pelarut etanol dan katalis piperidin dengan metode sonikasi selama 4 jam pada suhu 60 °C. Produk sintesis kemudian dielusidasi strukturnya dengan FTIR, KLT densitometer, 1H-NMR, dan 13C-NMR. Uji aktivitas antikanker dari senyawa kalkon dilakukan secara in vitro terhadap sel kanker serviks (HeLa), kolon (WiDr), dan sel normal (Vero).
Reaksi kondensasi Claisen-Scmidt menghasilkan kalkon 1 yang berwujud padatan kuning kecoklatan dengan titik leleh 172-174 °C dan persen hasil 53?ngan kemurnian 89%. Sementara kalkon 2 berupa padatan coklat dengan titik leleh 165-166 °C dan persen hasil 46?ngan kemurnian 90%. Uji sitotosisitas terhadap sel kanker HeLa, WiDr, dan Vero menunjukkan bahwa kalkon 1 memiliki aktivitas terbaik terhadap sel kanker WiDr dengan nilai IC50 3,72 µg/mL dan indeks selektivitas sebesar 6,77.

The synthesis of 3-acetylcoumarin-based chalcone derivatives and their evaluation for anticancer activity has been carried out. Chalcones 1 and 2 were synthesized through a Claisen-Schmidt condensation reaction between 3-acetylcoumarin and either 2-methoxybenzaldehyde or 3-methoxybenzaldehyde, using ethanol as the solvent and piperidine as the catalyst. The reaction was carried out under sonication for 4 hours at 60?°C. The resulting products were then characterized using FTIR, TLC densitometry, 1H-NMR, and 13C-NMR spectroscopy. The synthesized chalcone derivatives were tested in vitro for anticancer activity against HeLa (cervical cancer) and WiDr (colon cancer) cell lines, as well as normal Vero cells.
The Claisen-Schmidt condensation reaction produced chalcone 1 as a brownish-yellow solid with a melting point of 172-174 °C, a yield of 53%, and a purity of 89%. Chalcone 2 was obtained as a brown solid with a melting point of 165-166 °C, a yield of 46%, and a purity of 90%. Cytotoxicity assays against HeLa, WiDr, and Vero cells revealed that chalcone 1 exhibited the most potent activity with an IC50 value of 3.72 µg/mL and a selectivity index of 6.77 against WiDr cancer cells.

Kata Kunci : 3-asetilkumarin, antikanker, kalkon