SINTESIS TURUNAN KALKON DAN N-FENILPIRAZOLINA BERBAHAN DASAR 4-KLOROASETOFENON DAN 4-DIMETILAMINOBENZALDEHIDA SERTA UJI AKTIVITASNYA SEBAGAI ANTIMALARIA

Fauzia Rizky Triyuliyastuti, Dra. Tutik Dwi Wahyuningsih, M.Si., Ph.D; Prof. Drs. Sabirin Matsjeh, Ph.D

2019 | Skripsi | S1 KIMIA

Sintesis dan uji aktivitas antimalaria senyawa N-fenilpirazolina dari bahan dasar 4-kloroasetofenon dan 4-dimetilaminobenzaldehida (DMAB) telah dilakukan. Penelitian ini dilakukan melalui tiga tahap, yaitu sintesis senyawa kalkon dari 4-dimetilaminobenzaldehida dan 4-kloroasetofenon, sintesis senyawa N-fenilpirazolina dari senyawa kalkon dan fenilhidrazin, dan uji aktivitas antimalaria senyawa kalkon dan N-fenilpirazolina hasil sintesis. Sintesis senyawa kalkon dilakukan dengan metode pengadukan pada suhu ruang selama 15 menit dengan penambahan katalis basa KOH 40%. Sintesis senyawa N-fenilpirazolina dilakukan dengan mereaksikan kalkon hasil sintesis dengan fenilhidrazin dalam pelarut etanol menggunakan katalis basa KOH/etanol 40% dengan metode sonokimia selama 6 jam. Elusidasi struktur semua produk dilakukan menggunakan spektrometer FT-IR, GC-MS, 1H- dan 13C-NMR. Senyawa kalkon dan N-fenilpirazolina hasil sintesis diuji aktivitas antimalarianya secara in vitro dengan metode penghambatan polimerisasi hem. Sintesis kalkon menghasilkan produk (E)-3-(4-(dimetilamino)fenil)-1-(4-(klorofenil)-prop-2-en-1-on dengan rendemen 54%. Sintesis N-fenilpirazolina menghasilkan senyawa N-fenil-3-(4-klorofenil)-5-(4-(dimetilamino)fenil)-2-pirazolina dengan rendemen 67%. Uji antimalaria terhadap kalkon dan N-fenilpirazolina hasil sintesis memberikan nilai IC50 masing-masing sebesar 59,50 dan 34,60 mM. Hasil tersebut menunjukkan bahwa aktivitas antimalaria kedua senyawa tersebut tidak lebih baik dari aktivitas klorokuin difosfat sebagai senyawa standar (kontrol positif).

Synthesis and antimalarial test of N-phenylpyrazoline compound from 4-chloroacetophenone and 4-dimethylaminobenzaldehyde (DMAB) had been carried out. The research was carried out through three steps, i.e., the synthesis of chalcone from 4-dimethylaminobenzaldehyde and 4-chloroacetophenone, synthesis N-phenylpyrazoline from chalcone and phenylhidrazine, and antimalarial test of the chalcone and N-phenylpirazoline compound. Synthesis of chalcone was carried out by strirring method at room temperature for 15 minutes with the addition of KOH 40% as a base catalyst. The synthesis of N-phenylpyrazoline was performed by reacting the resulted chalcone with phenylhydrazine in ethanol and KOH/ethanol 40% with sonochemical methods for 6 hours. Elucidation structures of all products were carried out using FT-IR, GC-MS, 1H- and 13C-NMR spectrometers. Chalcone and N-phenylpyrazoline compounds were tested for antimalarial activity in vitro by inhibition of heme polymerization methods. The synthesis of chalcone compound produced [(E)-3-(4-(dimethylamino) phenyl)-1-(4-chlorophenyl)-prop-2-en-1-on] with a yield of 54%. Synthesis of N-phenylpyrazoline compound produced N-phenyl-3-(4-chlorophenyl)-5-(4-(dimethylamino)phenyl)-2-pyrazoline compound in 67% yield. The result of antimalarial activity test toward chalcone and N-phenylpyrazoline gave the IC50 values 59.50 and 34.60 mM, respectively. These result showed that the antimalarial activity of two compounds was lower than the activity of chloroquine diphosphate as a standard compound (positive control).

Kata Kunci : antimalaria, kalkon, N-fenilpirazolina, 4-kloroasetofenon