Sintesis dan Uji Sitotoksisitas Senyawa Kalkon dan Pirazolina dari 4-Asetilpiridin dan Turunan Benzaldehida terhadap Sel Kanker

ALIFTA SAFFA MAHANTARA, Prof. Dra. Tutik Dwi Wahyuningsih, M.Si., Ph.D.; Prof. Tri Joko Raharjo, S.Si., M.Si., Ph.D.

2025 | Skripsi | KIMIA

    Senyawa kalkon dan pirazolina diketahui memiliki potensi aktivitas antikanker. Pada penelitian ini dilakukan sintesis senyawa kalkon dan pirazolina dari 4-asetilpiridin dan turunan benzaldehida untuk kemudian diuji sitotoksisitasnya terhadap beberapa sel kanker. Kalkon A dan B disintesis melalui reaksi kondensasi Claisen-Schmidt dari reaktan 4-asetilpiridin dengan benzaldehida dan 4-metoksibenzaldehida. Reaksi dilakukan dengan metode pengadukan selama 24 jam pada suhu ruang dengan pelarut metanol dan katalis NaOH. Pirazolina A dan B disintesis melalui reaksi siklisasi kalkon A dan B dengan fenilhidrazina. Reaksi dilakukan dengan metode refluks menggunakan pelarut etanol dan katalis KOH. Seluruh senyawa dielusidasi strukturnya menggunakan spektroskopi GCMS, ATR-IR, 1H-, dan 13C-NMR. Uji sitotoksisitas dilakukan dengan menggunakan metode MTT terhadap sel kanker HeLa, WiDr, MCF-7, dan T47D serta sel normal Vero. 

    Sintesis kalkon A menghasilkan padatan putih dengan persen hasil 75?n kemurnian 92,16%, sedangkan kalkon B menghasilkan padatan putih kecokelatan dengan persen hasil 83?n kemurnian 98,63%. Sintesis pirazolina A menghasilkan padatan cokelat dengan persen hasil 69?n kemurnian 97,36%, sedangkan pirazolina B menghasilkan padatan merah kecokelatan dengan titik leleh 97,8-99,5 ? dengan persen hasil 71?n kemurnian 85,89%. Hasil uji sitotoksisitas antikanker menunjukkan bahwa senyawa pirazolina B memiliki aktivitas tinggi terhadap sel kanker HeLa dan WiDr, masing-masing memiliki nilai IC50 1,93 dan 0,52 ?g/mL dengan indeks selektivitas berturut-turut 50,93 dan 189,32.

    Chalcones and pyrazolines are known to have potential anticancer activity. In this study, chalcones and pyrazolines were synthesized from 4-acetylpyridine and various benzaldehyde derivatives, and their cytotoxicity was subsequently evaluated against several cancer cell lines. Chalcone A and B were obtained via Claisen-Schmidt condensation of 4-acetylpyridine with benzaldehyde and 4-methoxybenzaldehyde, respectively. The reaction was carried out by stirring in methanol at room temperature for 24 hours using NaOH as a catalyst. Subsequently, pyrazolines A and B were synthesized through cyclization of the corresponding chalcones with phenylhydrazine under reflux in ethanol using KOH as a catalyst. The chemical structures of all synthesized compounds were elucidated using GCMS, ATR-IR, 1H-, and 13C-NMR spectroscopy. Cytotoxicity activity was assessed using the MTT method against HeLa, WiDr, MCF-7, and T47D cancer cell lines as well as normal Vero cells.  

    The synthesis of chalcone A yielded a white solid with a yield of 75% and purity of 92.16%, whereas chalcone B was obtained as a brownish-white solid with a yield of 82% and purity of 98.63%. Pyrazoline A was synthesized as a brown solid with a yield of 69% and purity of 97.36%, while pyrazoline B was obtained as a red-brown solid with a yield of 71% and a purity of 85.89%. The anticancer assay revealed that pyrazoline B had the highest activity against HeLa and WiDr cancer cells, with IC50 values of 1.93 and 0.52 ?g/mL, respectively, and selectivity indexes of 50.93 and 189.32.

Kata Kunci : 4-asetilpiridin, kalkon, pirazolina, uji antikanker