Sintesis Hidrazona dari 5-Fluoroisatin dan 5-Kloroisatin

Ningtyas, Anggita (2024) Sintesis Hidrazona dari 5-Fluoroisatin dan 5-Kloroisatin. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Penyakit infeksi merupakan kondisi yang disebabkan oleh masuk dan berkembangnya mikroorganisme seperti bakteri dalam tubuh manusia. Infeksi oleh bakteri merupakan penyebab kematian terbesar kedua di dunia setelah penyakit jantung koroner. Global Burden of Diseases (GBD) tahun 2019 melaporkan bahwa terdapat 7,7 juta kematian yang disebabkan oleh 33 jenis infeksi bakteri. Sebagian bakteri telah mengalami resistensi terhadap antibiotik sehingga pengobatan penyakit infeksi yang disebabkan bakteri yang resisten terhadap antibiotik memerlukan pengembangan senyawa-senyawa antimikroba baru. Isatin (1a) dan turunannya memiliki bioaktivitas anti-TB, antibakteri, antijamur, antiviral, antitumor, anti-HIV, antiinflamasi, analgesik, antivirus, antelmintik, dan antioksidan. Reaksi senyawa-senyawa isatin dengan senyawa senyawa hidrazida diperoleh senyawa-senyawa hidrazona dengan bioaktivitas antibakteri, antikanker, antiinflamasi, antivirus, dan antiprotozoa. Hal tersebut memberikan berpeluang untuk mengembangkan senyawa-senyawa hidrazona baru sebagai turunan senyawa-senyawa isatin yang berperan sebagai antimikroba. Penelitian yang dilakukan berhasil mensintesis dua hidrazona dari 5-fluoroisatin (1b) dan 5-kloroisatin (1c) berupa N-(5-fluoro-2-oksoindolin-3-ilidena)furan-2-karbohidrazida (8a) dan N-(5-kloro-2-oksoindolin-3-ilidena)furan-2-karbohidrazida (8b). Senyawa hidrazona (8a) diperoleh dari reaksi yang melibatkan furan-2-karbohidrazida (3) dengan 5-fluoroisatin (1b) dalam pelarut etanol dengan katalis asam sulfat pekat, sedangkan senyawa hidrazona (8b) melalui reaksi yang melibatkan furan-2-karbohidrazida (3) dengan 5-kloroisatin (1c) dengan kondisi reaksi yang sama. Senyawa hidrazona (8a-b) masing-masing diperoleh dengan rendemen yang sama sebesar 82%. Struktur senyawa-senyawa hidrazona (8a-b) ditetapkan berdasarkan spektra 1H NMR, 13C NMR, IR, dan massa resolusi tinggi.
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Infection disease is a condition caused by the growth of microorganisms such as bacteria in human body. Infections caused by bacteria are the second leading cause of death in the world after coronary heart disease. Global Burden of Disease (GBD) reported in 2019 that there were 7.7 million deaths caused by 33 types of microbial infections. However, some bacteria have developed resistance to several antibiotics, making the treatment of infectious diseases caused by antibiotic-resistant bacteria necessitate the development of new antimicrobial compounds. Isatin (1a) and its derivatives exhibit various biological activities such as anti-TB, antibacterial, antifungal, antiviral, antitumor, anti-HIV, anti-inflammatory, analgesic, antivirus, anthelmintic, and antioxidant. Reaction between isatin and hydrazide compounds can produce hydrazone compounds, which are known to exhibit various biological activities such as antibacterial, anticancer, anti-inflammatory, antivirus, and antiprotozoal. Therefore, this research provides an opportunity to develop new hydrazone compounds as derivatives of isatin compounds that act as antimicrobial. Research has been succesfully to synthesize two hydrazones from 5-fluoroisatin (1b) and 5-chloroisatin (1c) form of: N-(5-fluoro-2-oxoindolin-3-ylidene)furan-2-carbohydrazide (8a) and N-(5-chloro-2-oxoindolin-3-ylidene)furan-2-carbohydrazide (8b). The hydrazone compound (8a) was obtained from reaction involving furoic-2-carbohydrazide (3) and 5-fluoroisatin (1b) in ethanol solvent using concentrated sulfuric acid as catalyst. On the other hand, the hydrazone compound (8b) was obtained through a reaction involving furoic-2-carbohydrazide (3) and 5-chloroisatin (1c) under the same reaction conditions. Both hydrazone compounds (8a-b) are obtained with an equal yield of 82%. Structural identification of compounds (8a-b) were determined based on 1H NMR, 13C NMR, IR, and high-resolution mass spectra.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	5-fluoroisatin, 5-kloroisatin, furan-2-karbohidrazida, hidrazona, 5-chloroisatin, 5-fluoroisatin, furoic-2-carbohydrazide, hydrazone
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:	Anggita Ningtyas
Date Deposited:	16 Feb 2024 06:52
Last Modified:	16 Feb 2024 06:52
URI:	http://repository.its.ac.id/id/eprint/107238

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