SYNTHESIS AND ACTIVITY EVALUATION OF CHALCONE AND PYRAZOLINE DERIVATIVES FROM FURFURALDEHYDE AS ANTIMALARIAL AGENTS

INTAN NADIRA, Dra. Tutik Dwi Wahyuningsih, M.Si., Ph.D.; Drs. Bambang Purwono, M.Sc., Ph.D.

2021 | Skripsi | S1 KIMIA

Sintesis senyawa turunan kalkon dan pirazolina dari furfuraldehida dan turunan asetofenon, yaitu 4-kloroasetofenon, 4-aminoasetofenon, dan 4-hidroksiasetofenon, telah dilakukan. Kalkon A, B, dan C disintesis melalui reaksi kondensasi Claisen-Schmidt. Sintesis kalkon A, B, dan C dilakukan dengan mereaksikan furfuraldehida dan turunan asetofenon dalam pelarut metanol:akuades (1:1) untuk kalkon A, B dan pelarut etanol untuk kalkon C dengan katalis NaOH 20% melalui pengadukan selama 24 jam pada suhu ruang. Sintesis N-fenilpirazolina A, B, dan C dilakukan dengan mereaksikan kalkon A, B, dan C dengan fenilhidrazina dalam pelarut etanol menggunakan katalis NaOH 20% melalui metode refluks dan metode pengadukan. Semua produk hasil sintesis dikarakterisasi menggunakan spektrometer FTIR, GC-MS, 1H and 13C-NMR. Aktivitas antimalaria dari produk hasil sintesis diuji secara in vitro terhadap Plasmodium falciparum FCR-3. Hasil penelitian menunjukkan bahwa kalkon A, B, dan C menghasilkan padatan dengan warna beragam dari coklat muda hingga kuning tua dengan rendemen berturut-turut yaitu 90,26; 93,79; dan 82,16%. N-fenilpirazolina A didapatkan sebagai padatan berwarna putih kecoklatan dengan rendemen sebesar 67,50%, sedangkan N-fenilpirazolina B didapatkan sebagai padatan berwarna merah kecoklatan dengan rendemen 88,17%. Uji antimalaria terhadap kalkon A, B, C, and N-fenilpirazolina A menghasilkan nilai IC50 masing-masing sebesar 24,44; 20,42; 21,92; dan 498,29 mikromolar. Dari penelitian ini disimpulkan bahwa kalkon A, B, dan C merupakan agen antimalaria dengan aktivitas sedang, sedangkan N-fenilpirazolina A dikategorikan sebagai senyawa yang tidak aktif sebagai antimalaria.

The synthesis of chalcone and pyrazoline derivatives has been carried out from furfuraldehyde and acetophenone derivatives, including 4-chloro-acetophenone, 4-aminoacetophenone, and 4-hydroxyacetophenones, as the starting materials. Chalcone A, B, and C were synthesized via Claisen-Schmidt condensation reaction using NaOH 20% as a catalyst. The synthesis was done by reacting the acetophenone derivatives, NaOH 20%, and furfuraldehyde in methanol:water (1:1) solvent for chalcone A, B, and ethanol solvent for chalcone C, under stirring at room temperature. The synthesis of N-phenylpyrazoline A, B, and C was carried out by reacting chalcone A, B, or C with phenylhydrazine in ethanol using NaOH 20% as a catalyst under reflux or stirring method. All the products were characterized by FTIR, GC-MS, 1H, and 13C-NMR spectrometers. The antimalarial activities of the synthesized compounds were evaluated through in vitro assay against Plasmodium falciparum FCR-3. The results showed that Chalcone A, B, and C were obtained as solids ranging in color from light brown, dark yellow, to yellowish-orange, with the yield of 90.26; 93.79; and 82.16%, respectively. N-phenylpyrazoline A was obtained as a whitish-brown solid in 67.50% yield, while N-phenylpyrazoline B was obtained as a reddish-brown solid in 88.17% yield. The antimalarial activity evaluation of chalcone A, B, C, and N-phenylpyrazoline A resulted in the IC50 values of 24.44; 20.42; 21.92; and 498.29 micromolar, respectively. From this research can be concluded that chalcone A, B, and C exhibited moderate antimalarial activity, while N-phenylpyrazoline A was inactive as an antimalarial agent.

Kata Kunci : 4-aminoacetophenone, antimalarial, chalcone, N-phenylpyrazoline, Plasmodium falciparum FCR-3