Sintesis Hidrazona dari 5-Bromoisatin dan 7-Bromoisatin

Hidayah, Novia Nurul (2024) Sintesis Hidrazona dari 5-Bromoisatin dan 7-Bromoisatin. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Isatin (1a) dan turunannya merupakan salah satu prekursor dalam sintesis senyawa organik yang memiliki bioaktivitas antibakteri, antijamur, antikanker, antiHIV, antituberkulosis, dan antivirus. Struktur isatin (1a) dapat dimodifikasi untuk mendapatkan senyawa-senyawa baru dengan bioaktivitas yang lebih baik. Modifikasi struktur dilakukan dengan menempatkan gugus pensubstitusi pada cincin aromatik cincin isatin maupun mereaksikan isatin (1a) dengan berbagai nukleofil maupun elektrofil. Furan-2-karbohidrazida (2) merupakan senyawa dengan bioaktivitas antibakteri, antileukemia, dan antimikoplasma. Reaksi antara isatin (1a) atau turunannya dengan senyawa hidrazida diperoleh hidrazona dengan bioaktivitas antiinflamasi, antioksidan, antimikroba, antikanker, anti-HIV, dan antiTB. Penelitian yang dilakukan berhasil memodifikasi struktur 5-bromoisatin (1b) dan 7-bromoisatin (1d) sehingga diperoleh senyawa-senyawa hidrazona baru berupa N-(5-bromo-2-oksoindolin-3-ilidena)furan-2-karbohidrazida (9a) dan N-(7-bromo-2-oksoindolin-3-ilidena)-furan-2-karbohidrazida (9b). Modifikasi struktur 5-bromoisatin (1b) dan 7-bromoisatin (1d) dilakukan dengan mereaksikan furan-2-karbohidrazida (2) dengan 5-bromoisatin (1b) atau 7-bromoisatin (1d) dalam pelarut etanol pada kondisi asam. Uji kemurnian senyawa-senyawa hidrazona (9a-b) dilakukan menggunakan kromatografi lapis tipis (KLT) dan titik leleh. Identifikasi struktur senyawa-senyawa hidrazona (9a-b) dilakukan dengan spektrometer NMR (1H, 13C), spektrofotometer FTIR, dan spektrometer massa resolusi tinggi (HRMS). Senyawa hidrazona N-(5-bromo-2-oksoindolin-3-ilidena)furan-2-karbohidrazida (9a) diperoleh dengan rendemen sebesar 90%, sedangkan senyawa hidrazona N-(7-bromo-2-oksoindolin-3-ilidena)-furan-2-karbohidrazida (9b) diperoleh dengan rendemen sebesar 84%.
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Isatin (1a) and its derivatives are one of the precursors in the synthesis of organic compounds which have antibacterial, antifungal, anticancer, antiHIV, antituberculosis and antiviral bioactivity. The structure of isatin (1a) can be modified to obtain new compounds with better bioactivity. Structural modification is carried out by placing a substitution group on the aromatic ring of the isatin ring or reacting isatin (1a) with various nucleophiles and electrophiles. Furan-2-carbohydrazide (2) is a compound with antibacterial, antileukemic and antimycoplasma bioactivity. The reaction between isatin (1a) or its derivatives with hydrazide compounds produces hydrazone with anti-inflammatory, antioxidant, antimicrobial, anticancer, anti-HIV and anti-TB bioactivity. The research carried out succeeded in modifying the structure of 5-bromoisatin (1b) and 7-bromoisatin (1d) to obtain new hydrazone compounds in the form of N-(5-bromo-2-oxoindolin-3-ylidene)furan-2-carbohydrazide (9a) and N-(7-bromo-2-oxoindolin-3-ylidene)-furan-2-carbohydrazide (9b). Modification of the structure of 5-bromoisatin (1b) and 7-bromoisatin (1d) was carried out by reacting furan-2-carbohydrazide (2) with 5-bromoisatin (1b) or 7-bromoisatin (1d) in ethanol solvent under acidic conditions. The purity test for hydrazone compounds (9a-b) was carried out using thin layer chromatography (TLC) and melting point. Identification of hydrazone compounds (9a-b) was carried out using an NMR spectrometer (1H, 13C), FTIR spectrophotometer, and high resolution mass spectrometer (HRMS). The hydrazone compound N-(5-bromo-2-oxoindolin-3-ylidene)furan-2 carbohydrazide (9a) was obtained with a yield of 90%, while the hydrazone compound N-(7-bromo-2-oxoindolin-3-ylidene)- furan-2-carbohydrazide (9b) was obtained with a yield of 84%.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	5-Bromoisatin, 7-Bromoisatin, Furan-2-karbohidrazida, Hidrazona, Furan-2-carbohydrazide, Hydrazones
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:	Novia Nurul Hidayah
Date Deposited:	17 Feb 2024 07:44
Last Modified:	17 Feb 2024 07:44
URI:	http://repository.its.ac.id/id/eprint/107239

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