Sintesis Kalkon dari 3-asetilkumarin dan Turunan Benzaldehida serta Uji Aktivitasnya sebagai Senyawa Antikanker

Pindi Susiloningsih, Prof. Dra. Tutik Dwi Wahyuningsih, M.Si., Ph.D. ; M. Idham Darussalam Mardjan, S.Si., M.Sc., Ph.D.

2025 | Skripsi | KIMIA

Sintesis senyawa turunan kalkon berbahan dasar 3-asetilkumarin dengan berbagai turunan benzaldehida serta uji bioaktivitasnya sebagai senyawa antikanker telah dilakukan. Turunan benzaldehida yang digunakan dalam penelitian ini yaitu benzaldehida, 4-metoksibenzaldehida, dan 4-klorobenzaldehida. Sintesis dilakukan melalui reaksi kondensasi Claisen-Schmidt dengan pelarut etanol serta katalis basa piperidin. Elusidasi struktur senyawa produk dilakukan dengan instrumen FT-IR, KLT densitometer, serta 1H- dan 13C-NMR. Uji aktivitas senyawa dilakukan secara in vitro dengan metode MTT terhadap sel kanker HeLa, WiDr, 4T1 dan Vero. 

Sintesis kalkon A menghasilkan padatan kuning dengan titik leleh sebesar 186-187 ? dan persen hasil 89%. Pada sintesis kalkon B diperoleh padatan berwarna putih kekuningan dengan titik leleh sebesar 170-171 ? dan persen hasil 63%, sedangkan kalkon C diperoleh padatan berwarna kuning dengan titik leleh sebesar 201-203 ? dan persen hasil 49%. Hasil uji antikanker pada kalkon A;B;C terhadap sel kanker HeLa, WiDr, 4T1, dan Vero menunjukkan bahwa ketiga senyawa aktif dan selektif terhadap sel kanker yang diujikan. Kalkon C memiliki nilai IC50 terbaik pada sel kanker HeLa yaitu sebesar 0,24 µg/mL, sedangkan kalkon A memiliki nilai IC50 terbaik pada sel kanker WiDr dan 4T1 masing – masing sebesar 2,80 dan 4,86 µg/mL. Kalkon B memiliki nilai IC50 <20>C memiliki indeks selektivitas paling tinggi yaitu 291,38 terhadap Hela dan 23,87 terhadap WiDr, namun tidak selektif pada sel kanker 4T1.

The synthesis of chalcone derivatives based on 3-acetylcoumarin with various benzaldehyde derivatives and the evaluation of their bioactivity as anticancer compounds have been conducted. The benzaldehyde derivatives used in this study were benzaldehyde, 4-methoxybenzaldehyde, and 4-chlorobenzaldehyde. The synthesis was performed through the Claisen-Schmidt condensation reaction using ethanol as a solvent and piperidine as a base catalyst. The structural elucidation of the products was carried out using FT-IR, TLC densitometer, and ¹H- and ¹³C-NMR instruments. The bioactivity tests were performed in vitro using the MTT method against HeLa, WiDr, 4T1, and Vero cancer cell lines.

The synthesis of chalcone A produced a yellow solid with a melting point of 186–187 °C and a yield of 89%. Chalcone B was obtained as a pale yellow solid with a melting point of 170–171 °C and a yield of 63%. Meanwhile, chalcone C produced a yellow solid with a melting point of 201–203 °C and a yield of 49%. The results of anticancer assays of chalcones A;B;C against HeLa, WiDr, 4T1, and Vero cell lines demonstrated that all three compounds were active and selective toward the tested cancer cells. Chalcone C exhibited the best IC?? value on HeLa cancer cells, which was 0.24 µg/mL, while chalcone A had the best IC50 values on WiDr and 4T1 cancer cells of 2.80 and 4.86 µg/mL, respectively. Chalcone B had an IC50 value of less than 20 µg/mL, thus it was classified as toxic against the three tested cancer cell lines. Chalcone C has the highest selectivity index, namely 291.38 against HeLa and 23.87 against WiDr, but is not selective for 4T1 cancer cells.

Kata Kunci : benzaldehida, kalkon, kumarin, piperidin, senyawa kanker