Saputra, Dedi (2026) Sintesis 3-(5-(4-fluorofenil)-1-fenil-4,5-dihidro-1H-pirazol-3-il)-2H-kromen-2-on dan Sitotoksisitasnya terhadap Sel Kanker Kolorektal WiDr dan Sel Normal Vero. Other thesis, Institut Teknologi Sepuluh Nopember.
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Abstract
Calkon dan pirazolina merupakan dua kelompok senyawa organik yang memiliki berbagai aktivitas biologis. Pirazolina dapat disintesis melalui siklisasi calkon, sehingga calkon berperan penting sebagai senyawa prekursor dalam pengembangan turunan pirazolina dengan potensi aktivitas biologis yang lebih baik. Senyawa turunan pirazolina berpotensi untuk dikembangkan sebagai kandidat obat antikanker baru. Salah satu target utama pengembangan senyawa antikanker adalah kanker kolorektal, yaitu tumor ganas yang ditemukan pada kolon dan rektum, yang termasuk salah satu jenis kanker dengan prevalensi tertinggi di Indonesia. Terapi konvensional seperti kemoterapi masih menimbulkan efek samping serius, termasuk kardiotoksisitas dan resistensi obat, sehingga diperlukan pencarian senyawa antikanker alternatif yang lebih aman dan efektif. Penelitian yang dilakukan berhasil mendapatkan calkon (8) dengan rendemen 66 % dari reaksi kondensasi Claisen–Schmidt yang melibatkan 3-asetilkumarin (6) dan 4-fluorobenzaldehida (7) pada kondisi basa. Calcon (8) kemudian diidentifikasi menggunakan 1H NMR. Reaksi calkon (8) dengan fenilhidrazina (22) diperoleh senyawa pirazolina baru berupa senyawa 3-(5-(4-fluorofenil)-1-fenil-4,5-dihidro-1H-pirazol-3-il)-2H-kromen-2-on (5) dengan rendemen 22%. Pirazolina (5) kemudian diindentifikasi menggunakan FTIR, HRMS, (1H dan 13C) NMR. Pirazolina (5) mempunyai sitotoksisitas yang sangat rendah terhadap sel normal Vero (IC50 1722,21 µg/mL). Hasil uji juga mengungkap bahwa senyawa pirazolina (5) mempunyai sitotoksisitas yang sedang terhadap sel kolorektal WiDr (IC50 21,88) sehingga mempunyai indeks selektifitas yang tinggi (78,71) dan dapat disarankan sebagai kandidat senyawa antikanker kolorektal WiDr yang aman.
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Chalcones and pyrazolines are classes of organic compounds that exhibit a wide range of biological activities. Pyrazolines can be synthesized via the cyclization of chalcones; therefore, chalcones play an important role as precursor compounds in the development of pyrazoline derivatives with enhanced biological activity. Pyrazoline derivatives have attracted considerable attention as potential anticancer agents. One of the major targets in anticancer drug development is colorectal cancer, a malignant tumor of the colon and rectum and one of the most prevalent cancers in Indonesia. Conventional therapies such as chemotherapy are still associated with serious adverse effects, including cardiotoxicity and drug resistance, highlighting the need for safer and more effective alternative anticancer agents. Chalcone (8) was successfully synthesized with a yield of 66% via a Claisen–Schmidt condensation between 3-acetylcoumarin (6) and 4-fluorobenzaldehyde (7) under basic conditions and subsequently characterized by 1H NMR spectroscopy. Reaction of chalcone (8) with phenylhydrazine (22) afforded a novel pyrazoline derivative, namely 3-(5-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one (5), in 22% yield. The structure of pyrazoline (5) was confirmed by FTIR, HRMS, and (11H and 13C) NMR spectroscopy. Cytotoxicity evaluation revealed that pyrazoline (5) exhibited very low toxicity toward normal Vero cells (IC₅₀ = 1722.21 µg/mL), while showing potent cytotoxic activity against WiDr colorectal cancer cells (IC₅₀ = 21.88 µg/mL). The compound demonstrated a high selectivity index (78.71), indicating its potential as a safe and promising anticancer candidate against colorectal cancer.
| Item Type: | Thesis (Other) |
|---|---|
| Uncontrolled Keywords: | 4-Fluorobenzaldehida, Calkon, Pirazolina, Sel Kanker, Sel Normal, 4-Fluorobenzaldehyde, Chalcone, Pyrazoline, Cancer Cells. Normal Cells |
| 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: | Dedi Saputra |
| Date Deposited: | 05 Feb 2026 10:00 |
| Last Modified: | 05 Feb 2026 10:00 |
| URI: | http://repository.its.ac.id/id/eprint/132204 |
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