SINTESIS N-BENZOIL PIRAZOLINA BERBAHAN DASAR VERATRALDEHIDA DAN 4-KLOROASETOFENON SERTA UJI SITOTOKSISITASNYA TERHADAP BEBERAPA SEL KANKER

LUSI SUSANTI, Dr. Deni Pranowo, M.Si dan Dr. Tutik Dwi Wahyuningsih, M.Si., Ph.D.

2017 | Skripsi | S1 KIMIA

Sintesis N-benzoil pirazolina dengan bahan dasar veratraldehida dan 4-kloroasetofenon serta uji sitotoksisitasnya terhadap beberapa sel kanker telah dilakukan. Penelitian ini bertujuan untuk mempelajari sintesis N-benzoil pirazolina dari suatu senyawa kalkon berbahan dasar veratraldehida dan 4-kloroasetofenon serta mengetahui sitotoksisitas senyawa N-benzoil pirazolina hasil sintesis terhadap beberapa sel kanker. Penelitian diawali dengan sintesis senyawa kalkon yang dibuat dengan mereaksikan veratraldehida dan 4-kloroasetofenon dengan pelarut etanol menggunakan katalis basa NaOH 30% (b/v) dengan metode pengadukan. Tahap selanjutnya adalah sintesis N-benzoil pirazolina dengan cara mereaksikan senyawa kalkon, metanol, hidrazin monohidrat dan benzoil klorida dengan katalis asam asetat glasial menggunakan metode sonokimia. Produk yang terbentuk kemudian dianalisis dengan spektrometer FT-IR, GC-MS, 1H-NMR dan 13C-NMR. Uji sitotoksisitas dilakukan terhadap sel kanker WiDr, HeLa, MCF-7 dan T47D dengan metode MTT. Berdasarkan hasil penelitian dihasilkan senyawa kalkon berupa padatan berwarna kuning kehijauan dengan titik leleh 101,0 � 105,8 °C dan rendemen sebesar 64,70%. Senyawa N-benzoil pirazolina yang dihasilkan berupa padatan berwarna putih dengan titik leleh 164,8 � 165,2 oC dan rendemen sebesar 80,95%. Hasil uji sitotoksisitas N-benzoil pirazolina memberikan sitotoksik lemah terhadap WiDr dan tidak sitotoksik terhadap HeLa, MCF-7 dan T47D. Nilai IC50 senyawa N-benzoil pirazolina terhadap sel kanker WiDr, HeLa, MCF-7 dan T47D berturutturut sebesar 203,82; 1145,51; 1169,79 dan 2399,77 μg/mL.

Synthesis of N-benzoyl pyrazoline from veratraldehyde and 4-chloroacetophenone and its in vitro test as an anticancer agent have been conducted. The aim of this research was to study the formation of N-benzoyl pyrazoline from chalcone, which was yielded from reaction between veratraldehyde and 4-chloroacetophenone and also to test the cytotoxicity of N-benzoyl pyrazoline toward some cancer cells. The chalcone synthesis was carried out by stirring a mixture of veratraldehyde and 4-chloroacetophenone in ethanol solvent and used base catalyst of 30% NaOH (w/v). The next step was synthesis of N-benzoyl pyrazoline by reacting chalcone, methanol, hydrazine monohydrate, benzoyl chloride and acid catalyst of glacial acetic acid used sonochemistry methode. The structure elucidation was carried out by FT-IR, GC-MS, 1H-NMR and 13C-NMR spectrometers. Citotoxicity test was performed towards WiDr, HeLa, MCF-7 and T47D cancer cells with MTT method. This research produced chalcone as greenish-yellow solid with melting point of 101.0 � 105.8 °C and showed 64.70% yield. The N-benzoyl pyrazoline compound that was produced was a white solid with melting point of 164.8-165.2 °C and showed 80.95% yield. The cytotoxicity test showed that N-benzoyl pyrazoline has weak toxicity against WiDr cell, and no toxicity against HeLa, MCF-7 and T47D. The IC50 value of N-benzoyl pyrazoline against WiDr, HeLa, MCF-7 and T47D cancer cells was 203.82; 1145.51; 1169.79 dan 2399.77 μg/mL respectively

Kata Kunci : veratraldehida 4-kloroasetofenon, N-benzoil pirazolina, sitoksisitas