SINTESIS DAN UJI AKTIVITAS ANTIMALARIA SENYAWA TURUNAN KALKON DARI 2-KLOROASETOFENON DAN TURUNAN BENZALDEHIDA

MARETHA ESTER, Dr. Deni Pranowo, M.Si., dan Dra. Tutik Dwi Wahyuningsih, M.Si., Ph.D.

2020 | Skripsi | S1 KIMIA

INTISARI Sintesis dan uji aktivitas antimalaria terhadap senyawa turunan kalkon dari bahan dasar 2-kloroasetofenon dan turunan benzaldehida telah dilakukan. Penelitian ini dilakukan dengan empat tahap yaitu sintesis senyawa kalkon A (E)-1-(2-klorofenil)-3-fenil-2-propen-1-on dari 2-kloroasetofenon dengan benzaldehida, sintesis senyawa kalkon B (E)-1-(2-klorofenil)-3-(4-metoksifenil)-2-propen-1-on dari 2-kloroasetofenon dan 4-metoksibenzaldehida, sintesis senyawa kalkon C (E)-1-(2-klorofenil)-3-(4-metoksifenil)-2-propen-1-on dari 2-kloroasetofenon dan 3,4-dimetoksibenzaldehida, serta uji aktivitas antimalaria dari kalkon tersebut. Kalkon A, B, dan C disintesis dengan metode reaksi Claisen-Schmidt melalui teknik pengadukan 24 jam dalam pelarut etanol pada suhu kamar dengan penambahan katalis basa KOH 20%. Elusidasi struktur produk sintesis dilakukan dengan spektrometer FTIR, GC-MS, 1H- dan 13C-NMR. Senyawa turunan kalkon diuji aktivitas antimalaria secara in vitro terhadap Plasmodium falcifarum 3D7. Berdasarkan hasil penelitian diperoleh produk kalkon A, B, dan C berupa padatan berwarna kuning pucat dengan rendemen berturut-turut 80,81; 98,40; dan 94,71%. Produk kalkon mempunyai titik leleh berturut-turut 190-200; 92-95; 100-103 ºC. Uji aktivitas antimalaria terhadap kalkon A, B, dan C dihasilkan IC50 berturut-turut 9,85; 944,49; 21,71 μM. Dapat disimpulkan bahwa senyawa kalkon A tergolong senyawa aktif terhadap antimalaria, kalkon B senyawa tidak aktif terhadap antimalaria, dan kalkon C tergolong senyawa aktif sedang terhadap antimalaria.

ABSTRACT Synthesis and test of antimalarial activity chalcone derivatives from 2-chloroacetophenone and benzaldehyde derivatives have been carried out. This research was conducted using four methods, namely the synthesis of chalcone A (E)-1-(2-chlorophenyl)-3-phenyl-2-propen-1-one from 2-chloroacetophenone and benzaldehyde, chalcone B (E)-1-(2-chlorophenyl)-3-(4-methoxyphenyl)-2-propen-1-one from 2-chloroacetophenone and 4-methoxybenzaldehyde, chalcone C (E)-1-(2-chlorophenyl)-3-(3,4-methoxysiphenyl)-2-propen-1-one compounds from 2-chloroacetophenone and 3,4-dimethoxybenzaldehyde, and the antimalarial activity test. Chalcone A, B, and C were synthesized by the Claisen-Schmidt reaction method using the 24-hour stirring technique with ethanol at room temperature with the addition of a 20% KOH base catalyst. Elucidation of the structure of the synthesis product was performed using FTIR, GC-MS, 1H- and 13C-NMR spectrometers. Chalcone derivatives were tested for their antimalarial activity in vitro assay against Plasmodium falcifarum 3D7. Based on the research results, the products of chalcone A, B, and C were pale yellow solid with yields of 80.81; 98.40; and 94.71% respectifely. The chalcone product has a melting point of 190-200; 92-95; 100-103 ºC. The antimalarial activity test against chalcone A, B, and C resulted in IC50 respectively 9.85; 944.49; and 21.71 μM. It can be concluded that chalcone compounds A was categorized as active compounds against antimalarials, chalcone compounds B was categorized inactive compouds againts antimalarials, and chalcone compounds C was categorized as moderate activity compounds against antimalarials.

Kata Kunci : Kata kunci: 2-kloroasetofenon, antimalaria, kalkon, Plasmodium falcifarum 3D7.