Sintesis Turunan Kalkon Berbahan Dasar 6-Nitroveratraldehida dan Kloroasetofenon serta Uji Aktivitasnya Sebagai Senyawa Antimalaria

KHAIRUNNISA BR PURBA, Dr. Deni Pranowo, S.Si., M.Si.; Dra. Tutik Dwi Wahyuningsih, M.Si., Ph.D.

2022 | Skripsi | S1 KIMIA

Senyawa turunan kalkon berbahan dasar 6-nitroveratraldehida telah berhasil disintesis dan diuji aktivitasnya sebagai agen antimalaria terhadap P. falciparum 3D7. Senyawa turunan kalkon disintesis melalui reaksi kondensasi Claisen-Schmidt dengan mereaksikan 6-nitroveratraldehida dan kloroasetofenon menggunakan katalis NaOH 2 M dalam etanol dengan metode konvensional dan sonokimia menghasilkan produk (E)-1-(4-klorofenil)-3-(3,4-dimetoksi-6-nitrofenil)-prop-2-en-1-on (kalkon 1) dan (E)-1-(2-klorofenil)-3-(3,4-dimetoksi-6-nitrofenil)-prop-2-en-1-on (kalkon 2). Produk kalkon dimurnikan dengan metode rekristalisasi. Elusidasi struktur terhadap produk hasil sintesis dilakukan dengan spektrometer FTIR, GC-MS, 1H- dan 13C-NMR. Produk hasil sintesis diuji aktivitasnya sebagai senyawa antimalaria secara in vitro terhadap P. falciparum 3D7. Sintesis senyawa kalkon 1 baik dengan metode konvensional maupun sonokimia menghasilkan produk padatan berwarna hijau muda dengan titik lebur 175-178 ºC dengan rendemen masing-masing 32,29% dan 22,66%. Senyawa kalkon 2 yang dihasilkan menggunakan metode konvensional dan metode sonokimia berupa padatan berwarna kuning kehijauan dengan titik lebur 165-167 ºC dengan rendemen masing-masing 45,95% dan 27,05%. Uji aktivitas antimalaria senyawa kalkon 1 dan 2 memberikan nilai IC50 berturut-turut sebesar 2,42 dan 1,93 µM sehingga kalkon 1 dan kalkon 2 dapat digolongkan sebagai senyawa aktif antimalaria.

The chalcone derivatives from 6-nitroveratraldehyde had been successfully synthesized and the antimalarial agent activity of those compounds had been tested against P. falciparum 3D7. The chalcone derivatives were synthesized via Claisen-Schmidt condensation reaction by reacting 6-nitroveratraldehyde and chloroacetophenone in the presence of NaOH 2 M as a catalyst using conventional and sonochemical methods. These reaction produced (E)-1-(4-chlorophenyl)-3-(3,4-dimethoxy-6-nitrophenyl)-prop-2-en-1-one (chalcone 1) and (E)-1-(2-chlorophenyl)-3-(3,4-dimethoxy-6-nitrophenyl)-prop-2-en-1-one (Chalcone 2). The products were purified by recrystallization method and the structure elucidation was performed using FTIR, GC-MS, 1H- and 13C-NMR spectrometers. The antimalarial activity of this compound were tested by in vitro assay against P. falciparum strain 3D7. The result showed that chalcone 1 was prepared using conventional and sonochemical methods was obtained as green solid with 175-178 ºC melting points, 32.29% and 22.66% yields, respectively. Chalcone 2 was prepared using conventional and sonochemical methods was obtained as greenish yellow solid with 165-167 ºC melting points in 45.95% and 27.05% yields, respectively. The antimalarial activity test of chalcone 1 and 2 gave IC50 values of 2.42 and 1.93 µM. Chalcone 1 and 2 were classified as active antimalarial agents.

Kata Kunci : Antimalaria, Kalkon, P. falciparum 3D7, sonokimia.