Sintesis Turunan Isoniazid dan Bioaktivitasnya terhadap Mycobacterium tuberculosis H37Rv

Rizky, Karina Harley Aulia (2025) Sintesis Turunan Isoniazid dan Bioaktivitasnya terhadap Mycobacterium tuberculosis H37Rv. Other thesis, Institut Teknologi Sepuluh Nopember.

Text 5004201056-Undergraduated_thesis.pdf Restricted to Repository staff only until 1 April 2027. Download (3MB) | Request a copy

Abstract

Tuberkulosis (TB) merupakan salah satu penyakit yang menyebabkan kematian terbesar di dunia. Tuberkulosis disebabkan oleh bakteri Mycobacterium tuberculosis yang dapat ditularkan melalui udara. Resistensi M. tuberculosis terhadap obat TB merupakan ancaman serius bagi kesehatan, dalam bentuk isoniazid-resistant TB, rifampicin-resistant TB, multidrug-resistant TB, pre-XDR-TB, dan XDR-TB. Hal ini mendorong untuk dikembangkan senyawa-senyawa anti-tuberkulosis baru. Turunan isoniazid (1) dimanfaatkan sebagai lead compounds dalam pengembangan senyawa-senyawa anti-TB baru. Studi literatur yang dilakukan mendapatkan bahwa turunan isoniazid (1) dalam berupa N`-(5-metilfuran-2-karbonil)isonikotinohidrazida (14a) dan N`-(tiofena-2-karbonil)isonikotinohidrazida (14b) belum pernah disintesis dan diuji bioaktivitasnya terhadap M. tuberculosis, sehingga penelitian yang dilakukan bertujuan untuk mengungkap hal tersebut. Sintesis dilakukan dengan cara mereaksikan 5-metilfuran-2-karbonil klorida (15a) dan tiofena-2-karbonil klorida (15b) masing-masing dengan isoniazid (1) dan piridina (6) dalam pelarut asetonitril pada suhu ruang sehingga diperoleh N`-(5-metilfuran-2-karbonil) isonikotinohidrazida (14a) dan N`-(tiofena-2-karbonil) isonikotinohidrazida (14b) masing-masing dengan rendemen 54%. Uji kemurnian senyawa-senyawa 14a-b dilakukan dengan kromatografi lapis tipis dan titik leleh; sedangkan identifikasi struktur dilakukan dengan spektrometer massa resolusi tinggi, spektrometer NMR (13C dan 1H), dan spektrofotometer FTIR. Senyawa-senyawa 14a-b pada konsentrasi 25; 12,5; dan 6,25 μg/mL dapat menghambat pertumbuhan bakteri M. tuberculosis H37Rv, hal ini menandakan bahwa senyawa 14a-b mempunyai MIC kurang dari 6,25 μg/mL.
==================================================================================================================================
Tuberculosis (TB) is one of the diseases that causes the greatest death in the world. Tuberculosis is caused by the bacteria Mycobacterium tuberculosis which can be transmitted through the air. Resistance of M. tuberculosis to TB drugs is a serious threat to health, in the form of isoniazid-resistant TB, rifampicin-resistant TB, multidrug-resistant TB, pre-XDR-TB, and XDR-TB. This encourages the development of new anti-tuberculosis compounds. Isoniazid derivatives (1) are used as lead compounds in the development of new anti-TB compounds. Literature studies conducted found that isoniazid derivatives (1) in the form of N`-(5-methylfuran-2-carbonyl)isonicotinohydrazide (14a) and N`-(thiophene-2-carbonyl)isonicotinohydrazide (14b) have never been synthesized and tested for their bioactivity against M. tuberculosis, therefore the study conducted aims to reveal this. Synthesis was carried out by reacting 5-methylfuran-2-carbonyl chloride (15a) and thiophene-2-carbonyl chloride (15b) with isoniazid (1) and pyridine (6) respectively in acetonitrile at room temperature to obtain N`-(5-methylfuran-2-carbonyl)isonicotinohydrazide (14a) and N`-(thiophene-2-carbonyl)isonicotinohydrazide (14b) each with a yield of 54%. The purity test of compounds 14a-b was carried out by thin layer chromatography and melting points; while structural identification was carried out by High Resolution Mass Spectrometer, NMR spectrometer (13C and 1H), and FTIR spectrophotometer. Compounds 14a-b at concentrations of 25; 12.5; and 6.25 μg/mL can inhibit the growth of M. tuberculosis H37Rv bacteria, this indicates that compounds 14a-b have an MIC of less than 6.25 μg/mL.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	anti tuberculosis, acyl chloride, isoniazid, anti tuberkulosis, asil klorida, isoniazid
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:	Karina Harley Aulia Rizky
Date Deposited:	04 Feb 2025 01:03
Last Modified:	04 Feb 2025 01:03
URI:	http://repository.its.ac.id/id/eprint/117962

Actions (login required)

View Item