Sintesis Empat Senyawa Turunan Isoniazid

Widhayanti, Nur Ari (2025) Sintesis Empat Senyawa Turunan Isoniazid. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Organisasi Kesehatan Dunia (WHO) melaporkan bahwa pada tahun 2022 seperempat populasi manusia di dunia terinfeksi bakteri Mycobacterium tuberculosis (M. tb), dan 450.000 ribu jiwa meninggal karena resistensi terhadap obat lini terdepan TB. WHO menetapkan tujuan penekanan infeksi M. tb hingga 90% pada tahun 2015-2035. Isoniazid (INH) (1) menjadi salah satu obat paling efektif dalam pengobatan antituberkulosis dengan MIC 0,01–0,2 μg/ml (0,0729–1,458 μM). Resistensi terhadap INH (1) menimbulkan kesulitan dalam penatalaksanaan pengobatan TB. Hal ini memerlukan pengembangan senyawa-senyawa anti-TB baru dengan menemukan obat baru atau mendesain ulang obat lama dengan tujuan meningkatkan efikasi terapi INH (1). Turunan-turunan isonizid (1) dalam bentuk imina dimanfaatkan sebagai lead compound dalam pengembangan obat TB baru. Penelitian yang dilakukan telah berhasil mendapatkan empat turunan isoniazid (1) berupa senyawa N’-(4-metoksibenzilidena)isonikotinohidrazida (6a), N’-(4-metilbenzilidena)isonikotinohidrazida (6b), N’,N’’’-1,3-fenilenabis(metanaililidena)di(isonikotinohidrazida) (6c), dan N’,N’’’-1,2-fenilenabis(metanaililidena)di(isonikotinohidrazida) (6d). Sintesis keempat senyawa dilakukan dalam pelarut etanol dalam kondisi refluks tanpa katalis, dan diperoleh rendemen masing masing sebanyak 88; 94; 97; dan 93%. Uji kemurnian senyawa hidrazona 6a−d dilakukan dengan kromatografi lapis tipis dan titik leleh; identifikasi struktur senyawa hidrazona 6a−d dilakukan dengan spektrometer NMR (1H dan 13C), spektrometer IR, dan High Resolution Mass Spectrometer-Electrospray Ionization (HRMSESI).

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The World Health Organization (WHO) reports that by 2022 a quarter of the world’s human population will be infected with Mycobacterium tuberculosis (M. tb) and 450,000 people will die due to resistanve to front-line TB drugs. WHO set goal of reducing 90% M. tb infection by 2015-2023. Isoniazid (INH) (1) is one of the most effective antituberculosis drugs, with MIC of 0,01–0,2 μg/ml (0,0729–1,458 μM). Resistance to INH (1) poses diffivulities in the management of TB treatment. This requires the development of new anti-TB compounds by discovering new drugs or redisigning old drugs with the aim of improving the therapeutic efficacy of INH (1). Isoniazid derivatives (1) in imine from are utilized as lead compounds in the development of new TB drugs. The research conducted has succesully obtained four isoniazid (1) derivatives in the form N’-(4-methoxybenzilidene)isonicotinohydrazide (6a), N’-(4-methylbenzilidene)isonicotinohydrazide (6b), N’,N’’’-1,3-phenylenebis(methaneylylidene) di(isonicotinohydrazide) (6c), and N’,N’’’-1,2-phenylenebis(methaneylylidene)di(isonico-tinohydrazide) (6d). The synthesis four compound was carried out in ethanol solvent under reflux condition without a catalyst, and yield of 88; 94; 97; and 93%, respectively. The purity test of of hydrazona compounds 6a−d was evaluated thin layer chromatography and melting point; structural identification of hydrazona 6a−d was performed using Nuclear Magentic Resonance (1H and 13C NMR) spectroscopy, IR specstroscopy, and High Resolution Mass Spectrometry-Electrospay Ionization (HRMSESI).

Item Type:	Thesis (Other)
Uncontrolled Keywords:	antituberkulosis, adisi nukleofilik, hidrazona, imina, turunan isoniazid, antituberculosis, hydrazone, imine, isoniazid derivatives, nucleophilic addition
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry Q Science > QD Chemistry > QD471 Chemical compounds - Structure and formulas Q Science > QD Chemistry > QD481 Chemical structure.
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Nur Ari Widhayanti
Date Deposited:	04 Aug 2025 10:21
Last Modified:	04 Aug 2025 10:21
URI:	http://repository.its.ac.id/id/eprint/126004

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