Sintesis Tiga Senyawa Turunan Isoniazid-Indol

Latifa, Dewi Ayu (2026) Sintesis Tiga Senyawa Turunan Isoniazid-Indol. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Indonesia mencatat lebih dari 1 juta kasus tuberkulosis setiap tahunnya, menjadikannya sebagai salah satu negara dengan beban TB tertinggi di dunia. World Health Organization (WHO) Indonesia menyumbang sekitar 10% dari total kasus TB dunia. Data menunjukkan, pada 2024 terdapat sekitar 118.000 kematian akibat TB pada orang tanpa HIV dan 8.100 kematian pada orang dengan HIV di Indonesia. Pengobatan TB dilakukan dengan Isoniazid (1) dan rifampisin (5) dikenal sebagai multi drug-resistant (MDR), dan juga disebut extensively drug-resistant (XDR). WHO (2018) melaporkan terdapat 8% kasus TB yang resisten terhadap isoniazid (1) sehingga mengurangi keberhasilan program pengobatan standar awal enam bulan pertama. Resistensi terhadap isoniazid (1) pada tingkat apa pun akan menimbulkan kesulitan dalam penatalaksanaan pengobatan TB. Dalam bidang antimikroba, turunan indol (7) aktif terhadap berbagai bakteri patogen, termasuk bakteri yang menunjukkan resistansi terhadap antibiotik konvensional. Turunan-turunan isoniazid (1) dan indol (7) dalam bentuk imina dimanfaatkan sebagai lead compound dalam pengembangan obat TB terbaru. Penelitian yang dilakukan telah berhasil mendapatkan tiga turunan isoniazid-indol berupa senyawa (E)-N′-((indol-7-il)metilena)isonikotinohidrazida (9a), (Z)-N′-((4-nitro-1H-indol-3-il)metilena)isonikotino-hidrazida (9b), dan (E)-N′-((6-bromoindol-3-il)metilena)isonikotinohidrazida (9c). Sintesis ketiga senyawa dilakukan dalam pelarut etanol dalam kondisi refluks dengan katalis asa sulfat, dan diperoleh rendemen masing-masing senyawa berhasil memiliki besar yaitu 96,63%; 87,10%; dan 88,5%. Uji kemurnian senyawa hidrazona 9a-c dilakukan dengan kromatografi lapis tipis dan titik leleh; identifikasi struktur senyawa hidrazona 9a-c dilakukan dengan spektrometer NMR (1H dan 12C), spektrometer IR, dan High Resolution Mass Spectrometer-Electrospray Ionization (HRMS-ESI).
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Indonesia records more than 1 million cases of tuberculosis annually, making it one of the countries with the highest TB burden in the world. The World Health Organization (WHO) Indonesia contributes approximately 10% of the world's total TB cases. Data shows that in 2024 there will be approximately 118,000 deaths due to TB in people without HIV and 8,100 deaths in people with HIV in Indonesia. TB treatment is carried out with Isoniazid (1) and rifampicin (5) known as multi-drug-resistant (MDR), and also called extensively drug-resistant (XDR). WHO (2018) reported that 8% of TB cases are resistant to isoniazid (1) thus reducing the success of the initial standard treatment program in the first six months. Resistance to isoniazid (1) at any level will cause difficulties in managing TB treatment. In the field of antimicrobials, indole derivatives (7) are active against various pathogenic bacteria, including bacteria that show resistance to conventional antibiotics. Isoniazid (1) and indole (7) derivatives in the form of imine are used as lead compounds in the development of new TB drugs. The research conducted has succeeded in obtaining three isoniazid-indole derivatives in the form of compounds (E)-N′-((indole-7-yl)methylene)isonicotinohydrazide (9a), (Z)-N′-((4-nitro-1H-indole-3-yl)methylene)isonicotinohydrazide (9b), and (E)-N′-((6-bromoindole-3-yl)methylene)isonicotinohydrazide (9c). The synthesis of the three compounds was carried out in ethanol solvent under reflux conditions with sulfuric acid catalyst, and the yield of each compound was obtained successfully with a yield of 96.63%; 87.10%; and 88.5%. The purity test of hydrazone compounds 9a-c was carried out by thin layer chromatography and melting point; Identification of the structure of hydrazone compounds 9a-c was carried out using an NMR spectrometer (1H and 12C), IR spectrometer, and High Resolution Mass Spectrometer-Electrospray Ionization (HRMS-ESI).

Item Type:	Thesis (Other)
Uncontrolled Keywords:	antituberkulosis, adisi nukelofilik, hidrazona, indol, isoniazid .
Subjects:	Q Science Q Science > QD Chemistry Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Natural Science > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Dewi Ayu Latifa
Date Deposited:	04 Aug 2026 08:49
Last Modified:	04 Aug 2026 08:49
URI:	http://repository.its.ac.id/id/eprint/143532

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