Sintesis Turunan Kalkon dengan Bahan Dasar Kloroasetofenon dan Uji Aktivitasnya sebagai Antikanker

FATIH GHALBY MANAR, Dra. Tutik Dwi Wahyuningsih, M.Si., Ph.D.; Sugeng Triono, S.Si, M.Si

2021 | Skripsi | S1 KIMIA

Sintesis senyawa kalkon dengan bahan dasar kloroasetofenon dan uji aktivitasnya sebagai antikanker telah dilakukan. Penelitian dilakukan dalam dua tahap, yang pertama sintesis senyawa kalkon berupa kalkon A (1-(4-klorofenil)-3-fenil-2-propen-1-on) dari 4-kloroasetofenon dengan benzaldehida, kalkon B (1-(4-klorofenil)-3-[4-(dimetilamino)fenil]-2-propen-1-on) dari 4-kloroasetofenon dengan 4-dimetilaminobenzaldehida, kalkon C (1-(2-klorofenil)-3-fenil-2-propen-1-on) dari 2-kloroasetofenon dengan benzaldehida, dan kalkon D (1-(2-klorofenil)-3-[4-(dimetilamino)fenil]-2-propen-1-on) dari 2-kloroasetofenon dengan 4-dimetilaminobenzaldehida, yang kedua uji aktivitas antikanker senyawa kalkon hasil sintesis tersebut. Sintesis senyawa kalkon dilakukan dengan reaksi kondensasi Claisen-Schmidt menggunakan metode sonikasi dengan pelarut etanol dan katalis NaOH 30%. Elusidasi struktur produk sintesis dilakukan dengan spektrometer FTIR, GC-MS, 1H- dan 13C-NMR. Uji aktivitas antikanker senyawa kalkon dilakukan dengan metode MTT terhadap sel kanker 4T1. Hasil penelitian yang diperoleh menunjukkan kalkon A berupa padatan berwarna putih dengan rendemen 80,41%, kalkon B berupa padatan berwarna kuning dengan rendemen 84,06%, kalkon C berupa padatan berwarna putih kecoklatan dengan rendemen 72,16%, serta kalkon D berupa padatan berwarna jingga dengan rendemen 47,28%. Uji antikanker senyawa kalkon A, B, C dan D dihasilkan nilai IC50 masing-masing sebesar 24,73; >100; >100; dan 36,49 µg/mL dan masing-masing indeks selektivitas sebesar 0,834; 0,067; 5498,069; dan 11,966. Dari data tersebut, dapat disimpulkan bahwa kalkon A dan D tergolong senyawa aktif sedang sebagai antikanker tetapi kalkon B dan C tergolong senyawa inaktif sebagai antikanker.

Syntheses of chalcone derivatives from chloroacetophenone and their anticancer activity test have been carried out. This research was conducted in two phases. The first one was syntheses of chalcone compounds, which are chalcone A (1-(4-chlorophenyl)-3-phenyl-2-propen-1-one from 4-chloroacetophenone with benzaldehyde, chalcone B (1-(4-chlorophenyl)-3-[4-(dimethylamino)phenyl]-2-propen-1-one) from 4-chloroacetophenone with 4-dimethylaminobenzaldehyde, chalcone C (1-(2-chlorophenyl)-3-phenyl-2-propen-1-one) from 2-chloroacetophenone with benzaldehyde, and chalcone D (1-(2-chlorophenyl)-3-[4-(dimethylamino)phenyl]-2-propen-1-one) from 2-chloroacetophenone and 4-dimethylaminobenzaldehyde. The second one was anticancer activity test of synthesized chalcone compounds. The synthesis of chalcone compounds was carried out with Claisen-Schmidt condensation reaction using sonication method with ethanol as solvent and NaOH 30% base catalyst. The structure elucidation of products was performed using FTIR, GC-MS, 1H- dan 13C-NMR spectrometers. Anticancer activity test of chalcone compounds was carried out using the MTT assay method against 4T1 cancer cells. The result showed that chalcone A was obtained as a white solid in 80.41% yields, chalcone B as a yellow solid with yields of 84.06%, chalcone C as as a brownish white solid with yields of 72.16%, and chalcone D as an orange solid with yields of 47.28%. Anticancer test of chalcone A, B, C dan D resulted in IC50 value of 24.73; >100; >100; and 36.49 µg/mL, respectively. In addition, the selectivity index of chalcone A and D were 0.834; 0.067; 5498.069; and 11.966, respectively. It can be concluded that chalcones A and D were categorized as moderate activity as anticancer, but chalcone B and C were categorized as inactive compounds as anticancer.

Kata Kunci : antikanker, kalkon, kloroasetofenon, sel kanker 4T1.