Sintesis Tiga 3,3-Di(indol-3-il)-indolin-2-on Baru

Titisari, Dyah Ayu (2021) Sintesis Tiga 3,3-Di(indol-3-il)-indolin-2-on Baru. Masters thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Kanker merupakan penyakit yang disebabkan pertumbuhan sel-sel baru secara abnormal yang tidak terkendali, yang kemudian menyerang bagian tubuh yang berdekatan dan menyebar ke organ lain. Kemoterapi merupakan salah satu cara pengobatan kanker yang efektif, namun memiliki efek samping yang memungkinkan dapat meracuni dan menyerang sel-sel normal. Sehubungan hal tersebut diperlukan pengembangan senyawa-senyawa baru yang menunjukkan aktivitas antikanker yang lebih baik dibandingkan dengan kemoterapi. Studi literatur mengungkap bahwa senyawa-senyawa 3,3-di(indol-3-il)indolin-2-on dapat dimanfaatkan sebagai lead compounds dalam pengembangan senyawa-senyawa antikanker. Penelitian yang dilakukan berhasil mensintesis tiga 3,3-di(indol-3-il)indolin-2-on baru berupa 5-bromo-1-(2-fenilbenzil)-3,3-di(1-(2-fenilbenzil)-indol-3-il)indolin-2-on (3a), 5-bromo-3,3’-di(1-(2-fenilbenzil)indol-3-il)indolin-2-on (3b), dan 5-bromo-1-(2-fenilbenzil)-3,3-di(1H-indol-3-il)indolin-2-on (3c). N-Benzilasi 5-bromoisatin (7) diperoleh 5-bromo-1-(2-fenilbenzil)indolin-2,3-dion (8) dengan rendemen 42%. Reaksi substitusi aromatik elektrofilik indola (6) dengan elektrofil berupa 5-bromo-1-(2-fenilbenzil)indolin-2,3-dion (8) diperoleh 5-bromo-1-(2-fenilbenzil)-3,3-di(1H-indol-3-il)indolin-2-on (3c). N-Benzilasi indola (6) diperoleh 1-(2-fenilbenzil)indola (5) dengan rendemen 79%. Reaksi substitusi aromatik elektrofilik 1-(2-fenilbenzil)indola (5) dengan elektrofil berupa 5-bromoisatin (7) diperoleh 5-bromo-3,3’-di(1-(2-fenilbenzil)indol-3-il)indolin-2-on (3b). N-Benzilasi senyawa 3b diperoleh 5-bromo-1-(2-fenilbenzil)-3,3-di(1-(2-fenilbenzil)indol-3-il)-indolin-2-on (3a).
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Cancer is a disease caused by the growth of new cells that are abnormally uncontrolled, then attack adjacent body parts and spread to other organs. Chemotherapy is one way of treating cancer, but it has side effects that allow it to poison and attack normal cells. In connection with this, it is necessary to develop new compounds that show better anticancer activity compared to chemotherapy. Literature studies reveal that 3,3-di(indol-3-yl)indolin-2-one compounds can be used as lead compounds in the development of anticancer compounds. The research carried out succeeded in synthesizing three new 3,3-di(indol-3-yl)indolin-2-one in the form of 5-bromo-1-(2-phenylbenzyl)-3,3-di(1-(2-phenylbenzyl)-indol-3-yl)indolin-2-one (3a), 5-bromo-3,3'-di(1-(2-phenylbenzyl)indolin-3-yl)indolin-2-one (3b), and 5-bromo-1-(2-phenylbenzyl)-3,3-di(1H-indol-3-yl)indolin-2-one (3c). N-Benzylation of 5-bromoisatin (7) obtained 5-bromo-1-(2-phenylbenzyl)-indolin-2,3-dione (8) with a yield of 42%. Electrophilic substitution reaction of indole (6) with an electrophile of 5-bromo-1-(2-phenylbenzyl)indolin-2,3-dione (8) obtained 5-bromo-1-(2-phenylbenzyl)-3,3-di (1H-indole-3-yl)indoline-2-one (3c). N-Benzylation of indole (6) was obtained 1-(2-phenylbenzyl)indole (5) with a yield of 79%. Electrophilic substitution reaction of 1-(2-phenylbenzyl)indole (5) with an electrophile of 5-bromoisatin (7) obtained 5-bromo-3,3'-di(1-(2-phenylbenzyl)-indole-3-yl)indolin-2-on (3b). N-Benzylation of compound 3b obtained 5-bromo-1-(2-phenylbenzyl)-3,3-di(1-(2-phenylbenzyl)indol-3-yl)-indolin-2-one (3a).

Item Type:	Thesis (Masters)
Uncontrolled Keywords:	Synthesis, 3,3-di(indole-3-yl)indolin-2-on, cancer
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47101-(S2) Master Thesis
Depositing User:	Dyah Ayu Titisari
Date Deposited:	27 Aug 2021 03:51
Last Modified:	27 Aug 2021 03:51
URI:	http://repository.its.ac.id/id/eprint/89898

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