Sintesis Senyawa-Senyawa Baru Turunan 5-Bromoisatin

Adawiyah, Robi'atul (2021) Sintesis Senyawa-Senyawa Baru Turunan 5-Bromoisatin. Masters thesis, Institut Teknologi Sepuluh Nopember.

	Text Tesis__Robi'atul Adawiyah_01211850010012-.pdf - Accepted Version Restricted to Repository staff only until 1 October 2023. Download (4MB) | Request a copy
	Text Tesis__Robi'atul Adawiyah_01211850010012-.pdf - Accepted Version Restricted to Repository staff only Download (4MB) | Request a copy

Abstract

Isatin (1) adalah turunan dari indola (2) yang memiliki berbagai macam bioaktivitas, sehingga dapat dijadikan sebagai prekursor untuk pengembangan senyawa obat. Turunan isatin berupa trisindolina (3) merupakan senyawa potensial dalam pengembangan senyawa obat, sehingga penelitian yang diusulkan bertujuan untuk mendapatkan tiga senyawa baru trisindolina (8-10) yang merupakan turunan 5-bromoisatin (14). Senyawa 8–10 masing-masing berhasil disintesis dalam dua tahap reaksi. Tahap pertama adalah reaksi N-benzilasi indola (2) yang melibatkan reaksi indola (2), natrium hidrida, dan 2-halobenzil bromida (15–17) dalam pelarut N,N-dimetilformamida pada suhu ruang diperoleh 1-(2-halobenzil)indola (11–13) dengan rendemen 60-69%; dua diantaranya merupakan senyawa baru. Tahap kedua adalah reaksi substitusi aromatik elektrofilik 1-(2-halobenzil)indola (11–13) dengan elektrofil 5-bromoisatin (14) dalam pelarut tetrahidrofuran dengan katalis asam sulfat diperoleh trisindoina baru 8–10 dengan rendemen masing-masing 63-75%. Identifikasi struktur senyawa-senyawa baru dilakukan dengan spektrometer resonansi magnet inti (1H dan 13C), spektrofotometer inframerah, dan spektrometer massa resolusi tinggi.
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Isatin (1) is indole derivative that covers a wide spectrum of biological activities. Isatin moiety (1) is extensively used as a precursor for drug discovery. Isatin derivative, known as trisindoline (3), is potential lead compounds for drug development. Thus, this research aims to afford new trisindoline compound (8-10) derived from 5-bromoisatin (14). Compound 8–10 has been synthesized through two stages of reaction. The first stage is indole (2) N-benzylation which was carried out by reaction of indole (2), sodium hydride, and 2-halobenzyl bromide (15–17) in N,N-dimethylformamide solvent to afford 1-(2-halobenzyl)indole (11–13) in 60-69% yield; two of the three are new compound. The second stage is electrophilic aromatic substitution of 1-(2-halobenzyl)indole (11–13) with 5-bromoisatin (14) electrophile in tetrahydrofuran solvent and the presence of sulphuric acid to give new compound 8–10 in 63-75% yield. Structure identification of the new compounds was carried out by nuclear magnetic resonance (1H and 13C) spectrometer, infrared spectrophotometer, and high resolution mass spectrometer.

Keywords: Synthesis, trisindoline, 5-bromoisatin, indole

Item Type:	Thesis (Masters)
Uncontrolled Keywords:	Sintesis, trisindolina, 5–bromoisatin, indola, Synthesis, trisindoline, indole
Subjects:	Q Science > QD Chemistry > QD471 Chemical compounds - Structure and formulas
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47101-(S2) Master Thesis
Depositing User:	Robi'atul Adawiyah
Date Deposited:	27 Aug 2021 04:10
Last Modified:	26 Jan 2022 05:25
URI:	http://repository.its.ac.id/id/eprint/89944

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