SYNTHESIS OF CHALCONE DERIVATIVES BASED ON 2-ACETYLFURAN AND METHOXYBENZALDEHYDES AND ITS ACTIVITY ASSAYS AS ANTIMALARIAL AGENT

RACHELIO C P, Dra. Tutik Dwi Wahyuningsih, M.Si., Ph.D.; Prof. Drs. Bambang Purwono, M.Sc., Ph.D

2022 | Skripsi | S1 KIMIA

Senyawa turunan kalkon disintesis melalui reaksi kondensasi Claisen- schimdt dari 2 -asetilfuran dan metoksibenzaldehida tersubstitusi sebagai agen antimalaria dan diuji aktifitas antimalaria. Sintesis turunan kalkon dilakukan menggunakan bahan dasar senyawa 2-asetilfuran dan metoksibenzaldehida tersubstitusi, yaitu 4-metoksi benzaldehida, 2,5-dimetoksibenzaldehida, 2,4- dimetoksibenzaldehida, 3,4-dimetoksibenzaldehida, 3,4,5 trimetoksibenzaldehida. Setiap metoksibenzaldehida tersubtitusi direaksikan dalam pelarut methanol:air 1:1 menggunakan katalis NaOH 20% dengan metode pengadukan. Elusidasi struktur terhadap produk hasil sintesis dilakukan dengan spectrometer FTIR, GC-MS, 1H- dan 13C-NMR. Produk hasil sintesis diuji aktivitasnya sebagai senyawa antimalaria secara in vitro terhadap Plasmodium falciparum FCR-3. Berdasarkan hasil penelitian diperoleh kalkon A, B, C, D dan E berupa padatan berwarna padatan kuning dengan rendemen berturut-turut 67.52, 80.62, 73.42, 81.51 and 78.69%, dengan titik leleh berturut-turut 92-95, 120-123, 108-111, 100-103, and 154-157 °C. Uji aktivitas malaria terhadap senyawa kalkon A-E menghasilkan nilai IC50 berturut turut 1.01; 1.04; 1.51; 2.17; dan 1.39 μM sehingga kalkon A-E tergolong senyawa yang aktif sebagai antimalaria. 2-Acetylfuran, antimalaria, kalkon, Plasmodium falciparum FCR-3

Chalcone derivatives were synthesized via Claisen-Schmidt condensation reaction from 2-acetylfuran and substituted methoxybenzaldehyde as antimalarial agents and underwent antimalarial activity assays. Synthesis of chalcone derivatives was carried out using 2-acetylfuran and substituted methoxybenzaldehyde, i.e., 4-methoxybenzaldehyde, 2,5-dimethoxybenzaldehyde, 2,4-dimethoxybenzaldehyde, 3,4-dimethoxybenzaldehyde and 3,4,5-trimethoxy- benzaldehyde as starting materials. Each substituted methoxybenzaldehyde was reacted in methanol: distilled water 1:1 and 20% NaOH catalyst under stirring to give chalcone A, B, C, D, and E. Then, structure elucidation of the synthesized product was done using FTIR, GC-MS, 1H- and 13C-NMR spectrometers. The product’s activities as antimalarial agents were tested by in vitro assay method against Plasmodium falciparum FCR-3. Chalcone A, B, C, D, and E were successfully synthesized from 2- acetylfuran and substituted methoxybenzaldehyde to give yellow solids in 67.52, 80.62, 73.42, 81.51 and 78.69% yields, respectively, with melting points of 92-95, 120-123, 108-111, 100-103, and 154-157 °C. Antimalarial activity assay of chalcone A, B, C, D, and E gave the IC50 values of 1.01; 1.04; 1.51; 2.17; and 1.39 μM, respectively. From in vitro antimalarial activity assay against Plasmodium falciparum FCR-3, it can be concluded that chalcone A, B, C, D, and E were categorized as good antimalarial agents. Keywords: 2-Acetylfuran, antimalaria, chalcone, Plasmodium falciparum FCR-3

Kata Kunci : 2-Acetylfuran, antimalaria, chalcone, Plasmodium falciparum FCR-3