SINTESIS TURUNAN KALKON DAN PIRAZOLINA DARI 2,4 DIMETOKSIASETOFENON SERTA UJI AKTIVITASNYA SEBAGAI SENYAWA ANTIMALARIA

FATHONI EGA MULYANA, Dra. Tutik Dwi Wahyuningsih, M.Si., Ph.D.; Dr. Endang Astuti, M.Si.

2020 | Skripsi | S1 KIMIA

Telah dilakukan sintesis turunan kalkon dan pirazolina berbahan dasar 2,4-dimetoksiasetofenon serta uji aktivitasnya sebagai antimalaria. Turunan kalkon disintesis melalui reaksi kondensasi Claisen-Schimdt. Sintesis kalkon A dan B dilakukan dengan mereaksikan benzaldehida atau p-anisaldehida dengan 2,4- dimetoksiasetofenon, dalam pelarut etanol menggunakan katalis NaOH 20% dan pengadukan selama 24 jam pada suhu ruang. Sintesis N- fenilpirazolina A dan B dilakukan dengan mereaksikan kalkon A atau kalkon B dengan fenilhidrazina dalam pelarut etanol dengan katalis NaOH 20% dan direfluks selama 24 jam. 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 Plasmodium falciparum 3D7. Berdasarkan hasil penelitian diperoleh kalkon A dan B berupa padatan berwarna kuning pucat dengan rendemen berturut-turut 87,96 dan 86,70% dan titik leleh 76-77 dan 86-87 derajat Celsius. Reaksi siklokondensasi menghasilkan N-Fenilpirazolina A berupa padatan berwarna coklat muda dengan rendemen 55,80% dan titik leleh 154-155 derajat Celcius, sedangkan N-fenilpirazolina B berupa padatan berwarna putih dengan rendemen 68,22% dan titik leleh 132-133 derajat Celsius. Uji aktivitas antimalaria terhadap senyawa kalkon A dan B serta senyawa N-fenilpirazolina A, dan B menghasilkan nilai IC50 berturut-turut 2,89; 1,29; 4,13; dan 29,18 µM. Dapat disimpulkan bahwa kalkon A, kalkon B dan N-fenilpirazolina A dikategorikan sebagai senyawa yang aktif sebagai antimalaria sedangkan N-fenilpirazolina B dikategorikan sebagai senyawa dengan aktivitas sedang sebagai antimalaria.

Synthesis of chalcone and pyrazoline derivative from 2,4-dimethoxyacetophenone and their activities test as antimalaria has been carried out. Chalcone derivatives were synthesized via Claisen-Schmidt condensation reaction. The synthesis of chalcone A and B was conducted by reacting benzaldehyde or panisaldehyde with 2,4-dimethoxyacetophenone in ethanol in the presence of NaOH 20% as a catalyst and it was stirred for 24 hours at room temperature. The synthesis of N-phenylpyrazoline A and B was carried out by reacting chalcone A or B with phenylhydrazine in ethanol using NaOH 20% as a catalyst under refluxed for 24 hours. Structure elucidation of all products was performed using FTIR, GC-MS, 1H- and 13C-NMR spectrometers. The synthesized products were tested for its activity as antimalarial compounds by in vitro assay against Plasmodium falciparum 3D7 The results showed that chalcone A and B were yielded as pale yellow solid in 87.96 and 86.70% with m.p of 86-87 and 86-87 degree Celsius, respectively. The cyclocondensation reaction produced N-phenylpyrazoline A as light brown solid in 55.80% with m.p 154-155 degree Celsius, while N-phenylpirazoline B was obtained as a white solid in 68.22% yield with m.p 132-133 degree Celsius. The antimalaria activity test of chalcone A, chalcone B, N-phenylpyrazoline A, and N-phenylpyrazoline B gave IC50 values of 2.89; 1.29; 4.13; dan 29.18 µM, respectively. It can be concluded that chalcone A, chalcone B, and N-phenylpyrazoline A were categorized as good antimalarial agents, while N-phenylpyrazoline B was categorized as a compound with moderate activity as antimalaria.

Kata Kunci : 2,4-dimetoksiasetofenon, antimalaria, kalkon, N-fenilpirazolina, Plasmodium falciparum 3D7