Crystallization of isoniazid in choline-based ionic liquids: Physicochemical properties and anti-tuberculosis activity

Reis, Carla Luzia Borges; Campelo, Thales Alves; Frota, Cristiane Cunha; Ayala, Alejandro Pedro; Silva, Lorena Mara Alexandre; Rocha, Maria Valderez Ponte; Santiago-Aguiar, Rílvia Saraiva de

doi:10.1016/j.molliq.2023.123671

Cited by 2 publications

(1 citation statement)

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“…Hydrazide–hydrazones are considered a fundamental framework for the development of potent and selective drugs due to their important biological activities such as antimicrobial, antioxidant, anticholinesterase, and anticarbonic anhydrase, as well as their pharmacological properties. − In addition, since these compounds are used in the discovery of new chemotherapeutic agents, the anticancer activities of many molecules containing the hydrazide–hydrazone moiety have been investigated to date. − Isoniazid is a drug frequently used in the treatment of tuberculosis. This drug is a first-line antimycobacterial drug commonly employed in combination with pyrazinamide, ethambutol, and rifampicin in the initial phase of treatment . Many analogues of this compound (Figure ), such as isocarboxazid, iproniazid, furazolidone, nifuroxazide, nitrofurantoin, and nitrofurazone, are also used in the management of various disorders. , …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and In Silico and In Vitro Cytotoxic Activities of Novel Isoniazid–Hydrazone Analogues Linked to Fluorinated Sulfonate Esters

Başaran,

Tür,

Akkoc

et al. 2024

ACS Omega

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Cancer is a life-threatening disease, and significant efforts are still being made to treat it. In this study, we synthesized and characterized novel hybrid molecules (10−18) containing hydrazone and sulfonate moieties and tested their cell growth inhibitory effect on human colon cancer cells (DLD-1), human prostate cancer cells (PC3), and human embryonic kidney cells (HEK-293T) using the 3-(4,5-dimethylthiazol-2-yl)-2,5diphenyl tetrazolium bromide (MTT) method for 72 h. In cell culture studies, all tested hybrid molecules except for 12 and 13 showed significant cytotoxic activities at a micromolar level with IC 50 values in the range of 10.28−214.0 μM for the PC3 cell line and 13.49−144.30 μM for the DLD-1 cell line. Compounds 4 (10.28 μM) and 5 (11.22 μM) demonstrated the highest cytotoxicity against the PC3 cell line. Against the DLD-1 cell line, compounds 1 (22.53 μM), 4 (13.49 μM), 5 (19.33 μM), 6 (17.82 μM), 8 (24.71 μM), 9 (17.56 μM), and 10 (17.90 μM) in the series showed anticancer activity at lower micromolar levels compared to cisplatin (26.70 μM). Moreover, the study was handled computationally, and molecular docking studies were performed for compounds 1, 4, and 5 for PC3-FAK and PC3-Scr and compounds 4, 6, and 9 for the DLD-1-TNKS target. In this study, compound 4 was found to be the most effective and promising molecule for both targets.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and In Silico and In Vitro Cytotoxic Activities of Novel Isoniazid–Hydrazone Analogues Linked to Fluorinated Sulfonate Esters

Başaran,

Tür,

Akkoc

et al. 2024

ACS Omega

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Design, Synthesis and In vitro Antitubercular Effect of New Chalcone Derivatives Coupled with 1,2,3‐Triazoles: A Computational Docking Techniques

Sadineni,

Reddy Basireddy,

Rao Allaka

et al. 2024

Chemistry & Biodiversity

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A very interesting foundation for this study is the creation of new methods for modifying compounds with a 1,2,3‒triazole and chalcones, as these compounds are significant in organic synthesis as bioactive organic compounds. To contribute to the development of an efficient method for the conversion of antimicrobial and anti‐TB drugs, a novel series of cyclohepta pyridinone fused 1,2,3–triazolyl chalcones were designed and synthesized. All the newly prepared scaffolds were characterized by IR, NMR (1H & 13C) and mass spectrometry. Among the tested compounds, hybrids 8b, 8d, and 8f exhibited exceptional antibacterial susceptibilities with zone of inhibition 27, 32, and 38 mm against the tested E. faecalis bacteria, whereas 8d had better antitubercular potency against M. tuberculosis H37Rv strain with MIC value 5.25 µg/mL. All the synthesized compounds were initially assessed in silico against the targeted protein i.e., DprE1 that indicated compound 8d, 8f and 8h along with several other 1,2,3‐triazole compounds as possible inhibitors. Based on docking results, 8d showed that the amino acids His74(A), Lys76(A), Cys332(A), Asp331(A), Val307(A), Tyr357(A), ect., exhibited highly stable binding to DprE1 receptor of M. tuberculosis (4G3U). Moreover, these scaffolds physicochemical characteristics, filtration molecular properties, assessment of toxicity, and bioactivity scores were assessed.

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Crystallization of isoniazid in choline-based ionic liquids: Physicochemical properties and anti-tuberculosis activity

Cited by 2 publications

References 42 publications

Design, Synthesis, and In Silico and In Vitro Cytotoxic Activities of Novel Isoniazid–Hydrazone Analogues Linked to Fluorinated Sulfonate Esters

Design, Synthesis, and In Silico and In Vitro Cytotoxic Activities of Novel Isoniazid–Hydrazone Analogues Linked to Fluorinated Sulfonate Esters

Design, Synthesis and In vitro Antitubercular Effect of New Chalcone Derivatives Coupled with 1,2,3‐Triazoles: A Computational Docking Techniques

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