Sintesis 3-(1-Fenil-5-(1H-pirol-2-il)-4,5-dihidro-1H-pirazol-3-il)-2H-krom-en-2-on dan Sitotoksisitasnya terhadap Sel Kanker Kolon WiDr dan Sel Normal Vero

Sidq, Mohammad Yusron (2026) Sintesis 3-(1-Fenil-5-(1H-pirol-2-il)-4,5-dihidro-1H-pirazol-3-il)-2H-krom-en-2-on dan Sitotoksisitasnya terhadap Sel Kanker Kolon WiDr dan Sel Normal Vero. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Kanker merupakan penyakit yang diakibatkan oleh sel tubuh yang mengalami mutasi, pertumbuhan yang tidak terkendali, dan membentuk massa (tumor) yang menyerang jaringan sekitar atau menyebar ke organ lain. Global Cancer Observatory melaporkan bahwa pada tahun 2022 terdapat 1.926.425 kasus kanker kolon global dengan 904.019 kematian. Kemoterapi penyakit kanker dilakukan menggunakan senyawa seperti cisplatin (1), 5-fluorourasil (5-FU) (2), dan doksorubisin (3); tetapi terapi tersebut memiliki efek samping. Pirazolina merupakan senyawa heterosiklik lima anggota dengan dua atom nitrogen dalam strukturnya, dan memiliki berbagai bioaktivitas termasuk anti kanker. Pada penelitian ini telah berhasil disintesis senyawa pirazolina baru berupa 3-(1-fenil-5-(1H-pirol-2-il)-4,5-dihidro-1H-pirazol-3-il)-2H-kromen-2-on (13) yang dilakukan dengan dua tahap. Tahap pertama melibatkan reaksi 3-asetilkumarin (9), pirol-2-karboksaldehida (10), piperidina (24) dalam pelarut etanol pada suhu 70°C selama empat jam sehingga diperoleh senyawa (E)-3-(3-(1H-pirol-2-il)akriloil)-2H-kromen-2-on (14) dengan rendemen 60%. Tahap kedua melibatkan dilakukan reaksi senyawa calkon (14), fenilhidrazina (5), piperidina (24) dalam pelarut etanol dan etil asetat pada suhu 70°C selama empat jam sehingga diperoleh pirazolina (13) dengan rendemen 31%. Pemantauan reaksi dilakukan dengan kromatografi lapis tipis, sedangkan pemurnian hasil reaksi dilakukan dengan kromatografi lapis tipis preparatif. Uji kemurnian senyawa calkon (14) dan pirazolina (13) dilakukan dengan kromatografi lapis tipis dan titik leleh. Identifikasi struktur senyawa calkon (14) dilakukan dengan spektrometer NMR (1H), sedangkan untuk senyawa pirazolina (13) dilakukan dengan spektrometer NMR (1H dan 13C), FTIR, dan HRMS. Senyawa pirazolina (13) memiliki sitotoksisitas terhadap sel kanker kolon WiDr dengan nilai IC50 sebesar 2,38 µg/mL sehingga tergolong dalam kategori kuat (IC50 < 20 µg/mL) dan tidak memiliki sitotoksisitas terhadap sel normal Vero dengan nilai IC50 sebesar 148525 µg/mL (IC50 >100 µg/mL), sehingga mempunyai indeks selektivitas sebesar 62405.
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Cancer is a disease of body cells that undergo mutations, uncontrolled growth, and form masses (tumors) that invade surrounding tissues or spread to other organs. The Global Cancer Observatory reported that in 2022 there were 1,926,425 cases of colon cancer globally with 904,019 deaths. Conventional cancer treatment methods used today include chemotherapy using compounds such as cisplatin (1), 5-fluorouracil (5-FU) (2), and doxorubicin (3). However, conventional treatment has several side effects and until now, treatment with new compounds such as pyrazolines has been developed. Pyrazolines are five-member heterocyclic ring compounds that have two nitrogen atoms in their structure and have a variety of different pharmacological activities such as anti-cancer. In this study, the synthesis of 3-(1-Phenyl-5-(1H-pyrrol-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-on (13) was successfully carried out. The synthesis of pyrazoline compound (13) was carried out in two steps. In the first step, (E)-3-(3-(1H-pyrrol-2-yl)acryloyl)-2H-chromen-2-on (7) was synthesized by reacting 3-acetylcoumarin (9), pyrrole-2-carboxaldehyde (10), piperidine (24) in ethanol solvent at a temperature of 70°C for four hours and a yield of 60.61% was obtained. The second step was carried out by cyclization of chalcone (14) with phenylhydrazine (5) using piperidine base catalyst (24) in ethanol and ethyl acetate solvents at 70°C for four hours and a yield of 31.42% was obtained. Purity tests of chalcone (14) and pyrazoline (13) compounds were carried out by thin layer chromatography and melting point. The chalcone compound (14) structure identification using NMR spectrometer (1H), while pyrazoline compound (13) structure identification was carried out by NMR spectrometer (1H and 13C), FTIR, and HRMS. The pyrazoline compound (13) has cytotoxicity against WiDr colon cancer cells with an IC50 value of 2.38 µg/mL so it is classified as strong (IC50 < 20 µg/mL) and has no cytotoxicity against normal Vero cells with an IC50 value of 148525 µg/mL (IC50 > 100 µg/mL), with a selectivity index of 62405.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	3-Asetilkumarin, Calkon, Pirazolina, Sel Kanker Kolon, Sel Normal 3-Acetylcoumarin, Chalcone, Pyrazoline, Colon Cancer, Vero
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Mohammad Yusron Sidqi
Date Deposited:	04 Feb 2026 07:44
Last Modified:	04 Feb 2026 07:44
URI:	http://repository.its.ac.id/id/eprint/132139

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