Green and efficient three-component synthesis of novel isoniazid pyrazoles, molecular docking, antioxidant and antitubercular evaluation

Koli, Bharti P.; Gore, Rambhau P.; Malasane, P. R.

doi:10.1080/00397911.2023.2235624

Synthetic Communications

2023

DOI: 10.1080/00397911.2023.2235624

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Green and efficient three-component synthesis of novel isoniazid pyrazoles, molecular docking, antioxidant and antitubercular evaluation

Bharti P. Koli

Rambhau P. Gore

P. R. Malasane

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2024

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Cited by 4 publications

References 45 publications

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Isoniazid Derivatives as Potential Lipoxygenase‐15 Inhibitors: In‐vitro and In‐silico Studies

Alghamdi,

Azam,

Jamir Anwar

et al. 2024

ChemistrySelect

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The enzymatic oxidation of polyunsaturated fatty acids, particularly arachidonic acid, produces important lipid mediators such as leukotrienes and prostaglandins, which are critical for triggering inflammatory cascades in the body. The enzyme lipoxygenase‐15 (LOX‐15) plays a crucial role in the oxygenation of unsaturated fatty acids. Targeting this enzyme for inhibition is essential for diminishing inflammation and averting numerous potentially fatal diseases. Therefore, the inhibitory activity of a series of isoniazid derivatives, selected from our in‐house library, was assessed against LOX‐15 by employing both in vitro and in silico methods. Among the 23 compounds evaluated, 15 showed activity in vitro. Notably, compound 7 was the most effective, demonstrating an IC50 value of 1.4±0.1 μM while the standard inhibitor, NDGA, showed an inhibition at 9.4±0.6 μM. These compounds were found to competitively inhibit LOX‐15, with Ki values ranging from 1.2–7.1 μM. Molecular docking was utilized to investigate the intermolecular interactions among the active compounds. The thermodynamic stability of the compound 7 and NDGA in complex with LOX‐15 was verified through 100 ns of molecular dynamics simulations. Post‐simulation analyses involved RMSD, RMSF, RoG, free energy landscape, principal component analysis, and dynamic cross‐correlation matrix. Compound 7 and NDGA had MM/GBSA binding energies of −54.14±2.55 kcal/mol and −35.24±3.23 kcal/mol, respectively. The study underscores the significant potential of isoniazid derivatives in LOX‐15 inhibition and their role in managing inflammatory diseases.

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Isoniazid Derivatives as Potential Lipoxygenase‐15 Inhibitors: In‐vitro and In‐silico Studies

Alghamdi,

Azam,

Jamir Anwar

et al. 2024

ChemistrySelect

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Isoniazid Hybrids As Potential Antitubercular Agents

Mishra,

Kumar,

Singh

2024

ChemistrySelect

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The rapid emergence of various forms of drug‐resistant tuberculosis (TB) has massively impacted people's health globally. According to the WHO, TB care and facilities have been downgraded by 21% since the COVID‐19 pandemic, which has further slowed down the progress toward the “End TB Strategy.” Multiple studies have shown drug‐resistant tuberculosis to be resilient to front‐line antituberculosis drugs, including isoniazid (INH), thus constantly prompting researchers worldwide to probe new potent chemical entities to replace/supplement the current artillery of anti‐TB therapeutics. The molecular hybridization (MH) technique has recently been adopted by many synthetic and medicinal chemists to combine different pharmacophoric units into a single molecular architecture which in most cases has been reported to exhibit a better pharmacological profile as compared to its precursors. The present review provides a concise account of the MH hybridization strategies directed at the structural manipulations of isoniazid to develop new anti‐TB agents and their structure‐activity relationships. Furthermore, their toxicity profiles and docking studies with relevant receptors are also briefly discussed.

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Ammonium Acetate as an Efficient and Greener Catalyst for the Synthesis of 1 H -Pyrazolo[1,2- b ]phthalazine-5,10-diones in an Aqueous Medium

Kanke,

Koli,

Gore

2024

Organic Preparations and Procedures International

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Green and efficient three-component synthesis of novel isoniazid pyrazoles, molecular docking, antioxidant and antitubercular evaluation

Cited by 4 publications

References 45 publications

Isoniazid Derivatives as Potential Lipoxygenase‐15 Inhibitors: In‐vitro and In‐silico Studies

Isoniazid Derivatives as Potential Lipoxygenase‐15 Inhibitors: In‐vitro and In‐silico Studies

Isoniazid Hybrids As Potential Antitubercular Agents

Ammonium Acetate as an Efficient and Greener Catalyst for the Synthesis of 1 H -Pyrazolo[1,2- b ]phthalazine-5,10-diones in an Aqueous Medium

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