The cleavage kinetics of hydrazide derivatives of isoniazid by HPLC-UV/DAD and its impact on activity against Mycobacterium tuberculosis

Three new 2,6-disubstituted thiosemicarbazone derivatives of pyridine, namely, 2-{amino[6-(pyrrolidin-1-yl)pyridin-2-yl]methylidene}-N,N-dimethylhydrazine-1-carbothioamide, C13H20N6S, 2-{amino[6-(piperidin-1-yl)pyridin-2-yl]methylidene}-N,N-dimethylhydrazine-1-carbothioamide, C14H22N6S, and 2-[amino(6-phenoxypyridin-2-yl)methylidene]-N,N-dimethylhydrazine-1-carbothioamide monohydrate, C15H17N5OS·H2O, have been synthesized and characterized by NMR spectroscopy and low-temperature single-crystal X-ray diffraction. In addition, their antibacterial and anti-yeast activities have been determined. The ability of the tested compounds to inhibit bacterial growth was comparable to vancomycin as a reference drug. Compared to isoniazid (MIC 0.125 and 8 µg ml−1), the compounds showed the ability to inhibit the growth of Mycobacterium tuberculosis to a moderate degree for the standard strain and at the same level or higher (MIC 4–8 µg ml−1) for the resistant strain. All three compounds adopt the zwitterionic form in the crystal structure regardless of the presence or absence of solvent molecules.

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Synthesis, structure, ADME and biological activity of three 2,6-disubstituted thiosemicarbazone derivatives

Ziembicka

Ołczak

Gobis

et al. 2023

Acta Crystallogr C

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Risk Prediction Model for Isoniazid Dosing in Tuberculosis Meningitis Patients in Southwest China

Zong,

Jian,

Zhu

et al. 2024

IJGM

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Synthesis, Molecular Docking, and In vitro Antimycobacterial Studies on N'-arylidene-4-nitrobenzohydrazides

Bhosale

Mali

Thorat

et al. 2022

RAAIDD

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Background: Mycobacterium tuberculosis (Mtb) is the organism that causes tuberculosis to develop (TB). In 2019, 10 million individuals worldwide contracted tuberculosis, with 1.4 million people dying from the disease each year (World Health Organization, 2021). Hydrazones-hydrazide-based drugs have been shown to be bactericidal against M. tuberculosis replication. Objectives: We herein intended to synthesize a series of acid hydrazones (3a-3l) by condensing 4-nitrobenzohydrazine with substituted aromatic acids in ethanol at room temperature. Materials and Methods: All newly synthesized compounds were characterized by standard spectroscopic techniques. Synthesized compounds were then tested for anti-mycobacterial analysis, H37Rv strains. Molecular docking analysis was performed for three crystal structures of 1ENY, 1TED and 2FUM Mycobacterium tuberculosis receptors. Results: Among all tested molecules, 3i (MIC: 50 μg/mL) and 3b (MIC: 50 μg/mL) were found to best ligands for further development of new anti-TB drug. We noticed that our proposed molecules were having higher docking scores that corresponding standard anti-TB agents such as Ciprofloxacin and Isoniazid. Synthesized compounds were found to have Drug-Likeness properties when tested with Lipinski’s filter for drug-likeness. Conclusion: From our current study, we wish to propose N'-arylidene-4-nitrobenzohydrazides as anti-TB agents. Agents with such system can be developed in future for developments into active lead molecules.

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The cleavage kinetics of hydrazide derivatives of isoniazid by HPLC-UV/DAD and its impact on activity against Mycobacterium tuberculosis

Cited by 3 publications

References 16 publications

Synthesis, structure, ADME and biological activity of three 2,6-disubstituted thiosemicarbazone derivatives

Synthesis, structure, ADME and biological activity of three 2,6-disubstituted thiosemicarbazone derivatives

Risk Prediction Model for Isoniazid Dosing in Tuberculosis Meningitis Patients in Southwest China

Synthesis, Molecular Docking, and In vitro Antimycobacterial Studies on N'-arylidene-4-nitrobenzohydrazides

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