Wulan, Diana Tri (2019) Sintesis Tiga Turunan 5-Hidroksiindola. Other thesis, Institut Teknologi Sepuluh Nopember.
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Abstract
Tuberkulosis (TB) merupakan penyakit infeksi kronis yang disebabkan bakteri Micobacterium tuberculosis yang dapat menyerang berbagai organ dalam tubuh terutama paru-paru. Resistensi obat TB lini pertama (Multidrug-resistant Tuberculosis (MDR-TB)) dan lini kedua (Eextensively Drug Resisten Tuberculosis (XDR-TB)) terhadap penderita TB mendorong untuk dikembangkan senyawa-senyawa antituberkulosis baru. Studi literatur menunjukkan bahwa trisindolina dapat dimanfaatkan sebagai lead compounds senyawa-senyawa antituberkulosis. Oleh karena itu, pada penelitian ini dilakukan sintesis 5,7-dibromo-3,3-di(5-hidroksindolil)indolin-2-on (10a), 7-kloro-3,3-di(5-hidroksiindolil)indolin-2-on (10b), dan 7-bromo-3,3-di(5-hidroksiindolil)indolin-2-on (10c). Hasil penelitian menunjukkan bahwa tiga trisindolina baru telah berhasil disintesis dengan mereaksikan masing-masing 5,7-dibromoisatin (13a), 7-kloroisatin (13b), dan 7-bromoisatin (13c) dengan 5-hidroksiindola (11) dalam pelarut metanol dan katalis asam sulfat pekat. Senyawa hasil sintesis yang diperoleh adalah 5,7-dibromo-3,3-di(5-hidroksindolil)indolin-2-on (10a), 7-kloro-3,3-di(5-hidroksiindolil)indolin-2-on (10b), dan 7-bromo-3,3-di(5-hidroksiindolil)indolin-2-on (10c) dengan rendemen masing-masing 96%, 52% dan 43%. Identifikasi struktur senyawa (10a-c) dilakukan dengan spektrometer massa resolusi tinggi (HRMS), NMR, dan IR.
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Tuberculosis is a chronic infectious disease caused by Micobacterium tuberculosis which can attack various organs in the body, especially lung. Resistance to first-line TB drugs (Multidrug-resistant Tuberculosis (MDR-TB)) and second-line (Extensively Drug Resisten Tuberculosis (XDR-TB)) to TB patients encourages new antituberculosis compounds the develop. Literature studies show that trisindoline can be used as the lead compounds for antituberculosis compounds. Therefore, in this study the synthesis of 5,7-dibromo-3,3-di (5-hydroxyindolyl)indolin-2-on (10a), 7-chloro-3,3-di (5-hydroxyindolyl) indolin-2-on (10b) and 7-bromo-3,3-di (5-hydroxyindolyl) indolin-2-on (10c) was carried out. The result showed that three new trisindoline were successfully synthesized by reacting each of 5,7-dibromoisatin (13a), 7-chloroisatin (13b), dan 7-bromoisatin (13c) and with 5-hydroxyindole (11) in methanol solvent and concentrated sulfuric acid as catalyst. The synthesized compounds obtained were 5,7-dibromo-3,3-di (5-hydroxyindolyl)indolin-2-on (10a), 7-chloro-3,3-di (5-hydroxyindolyl) indolin-2-on (10b) and 7-bromo-3,3-di (5-hydroxyindolyl) indolin-2-on (10c) with a yield of 96%, 52%, dan 43% respectively. Identification of the structure of the compounds (10a-c) was carried out with high resolution mass spectrometer (HRMS), NMR, and IR.
| Item Type: | Thesis (Other) |
|---|---|
| Additional Information: | RSKi 572.549 Wul s-1 2019 |
| Uncontrolled Keywords: | 5,7-dibromoisatin, 7-bromoisatin, 7-kloroisatin, 5-hidroksiindol, trisindolina |
| Subjects: | Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry |
| Divisions: | Faculty of Natural Science > Chemistry > 47201-(S1) Undergraduate Thesis |
| Depositing User: | Diana Tri Wulan |
| Date Deposited: | 18 Oct 2023 01:51 |
| Last Modified: | 18 Oct 2023 01:51 |
| URI: | http://repository.its.ac.id/id/eprint/64110 |
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