Kusman, Kusman (2007) Sintesis Dan Bioakvitas Tiga Turunan 3,3`- Bis (Indol- 3- Il ) Oksindola. Masters thesis, Institut Teknologi Sepuluh November.
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Abstract
Sintesis tiga turunan 3,3'-bis(indol-3-il)oksindol merupakan rangkaian penelitian untuk mengembangkan metode sintesis dan meningkatkan bioaktivitas 3,3'-bis(indol-3-il)oksindola dan turunannya. Ketiga turunan 3,3'-bis(indol-3-il)oksindola berhasil disintesis dalam satu tahap reaksi melibatkan substitusi elektrofilik 5-hidroksiindola dengan karbon karbonil isatin atau 5-haloisatin dengan rasio 2:1 dalam metanol. Sintesis 3,3'-bis(5-hidroksiindol-3-il)-5-bromoksindola dengan katalis boron trifluorida, zirkonil (IV) klorida dan asam sulfat, masing-masing memberikan rendemen secara berturut-turut 91%, 89% dan 94%. Asam sulfat yang menunjukkan rendemen lebih tinggi kemudian dimanfaatkan untuk sintesis 3,3'-bis(5-hidroksiindol-3-il)-5-kloroksindola dan 3,3'-bis(5-hidroksiindol-3-il)oksindola. 3,3'-Bis(5-hidroksiindol-3-il)-5-kloroksindola diperoleh dengan rendemen 97% dan 3,3'-bis(5-hidroksiindol-3-il)oksindola dengan rendemen 94%. Uji bioaktivitas menunjukkan bahwa ketiga senyawa bersifat bakteriostatik/bakterisidal terhadap bakteri Escherichia coli dan Bacillus subtilis. 3,3'-Bis(5-hidroksiindol-3-il)-5-bromoksindola mempunyai sifat bakteriostatik yang lebih kuat dibandingkan terhadap 3,3'-bis(indol-3-il)oksindola, dan 3,3'-bis(5-hidroksiindol-3-il)oksindola hampir sama dengan 3,3'-bis(indol-3-il)oksindola. 3,3'-Bis(5-hidroksiindol-3-il)-5-kloroksindola bersifat bakterisidal terhadap Bacillus subtilis dan Escherichia coli. 3,3'-Bis(indol-3-il)oksindola dan turunannya bersifat bakterisidal terhadap Bacillus subtilis dan 3,3'-Bis(5-hidroksiindol-3-il)-5-bromoksindola adalah yang lebih kuat.
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Synthesis of the three 3,3'-bis(indol-3-yl)oxindole derivatives has been carried out to develop the synthesis method and to improve their bioactivities. These derivatives have been successfully synthesised in one-step reaction via electrophilic substitution of 5-hydroxyindole with isatin or 5-haloisatins with ratio 2:1 in methanol solvent. Synthesis of 3,3'-bis(5-hydroxyindol-3-yl)-5-bromoxindole has been explored with boron trifluoride, zirconyl (IV) chloride and sulphuric acid as catalysts, each catalyst gave 91%, 89% and 94% yields respectively. Accordingly, sulphuric acid was used for the synthesis of 3,3'-bis(5-hydroxyindol-3-yl)-5-chloroxindole and 3,3'-bis(5-hydroxyindol-3-yl)oxindole, with respectively furnished 97% and 94% yields. The synthesis products showed bacteriostatic/bactericidal against Escherichia coli and Bacillus subtilis. 3,3'-Bis(5-hydroxyindol-3-yl)-5-bromoxindole is stronger against Escherichia coli and Bacillus subtilis compared with 3,3'-bis(indol-3-yl)oxindole, whilst 3,3'-bis(5-hydroxyindol-3-yl)oxindole is similar to 3,3'-bis(indol-3-yl)oxindole. 3,3'-Bis(5-hydroxyindol-3-yl)-5-chloroxindole exhibited bactericidal activity against Escherichia coli and Bacillus subtilis. 3,3'-Bis(indol-3-yl)oxindole and its derivatives showed bactericidal activity against Bacillus subtilis, in which 3,3'-bis(5-hydroxyindol-3-yl)-5-bromoxindole has the strongest properties.
| Item Type: | Thesis (Masters) |
|---|---|
| Additional Information: | RTKi 615.19 Kus s |
| Uncontrolled Keywords: | Sintesis, bioaktivitas, 5-bromoisatin, 5-hidroksiindola, 5-kloroisatin, 3,3'-bis(indol-3-il)oksindola, Synthesis, bioactivity, 5-bromoisatin, 5-chloroisatin, 3,3'-bis(indol-3-yl)oxindole, 5-hydroxyindole. |
| Subjects: | Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry |
| Divisions: | Faculty of Mathematics and Science > Chemistry > 47101-(S2) Master Thesis |
| Depositing User: | magang . |
| Date Deposited: | 02 Oct 2026 07:48 |
| Last Modified: | 02 Oct 2026 07:48 |
| URI: | http://repository.its.ac.id/id/eprint/145205 |
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