One-pot sonochemical synthesis and in silico/in vitro antitubercular evaluation of 1-methyl-3-propyl-1H-pyrazole containing polynuclear fused N-heteroarenes

Sangepu, Venkateswara Rao; Jain, Kuldeep; Bhoomireddy, Rama Devi; Sharma, Deepika; Venkateshwarlu, Rapolu; Kapavarapu, Ravikumar; Dandela, Rambabu; Pal, Manojit

doi:10.1016/j.molstruc.2023.134909

Cited by 4 publications

(1 citation statement)

References 34 publications

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“…Another example is the use of pyrano [2,3-c]pyrazole and pyrazolo [4 ,3 :5,6]pyrano [2,3-d]pyrimidine derivatives for their antimicrobial, antioxidant, and anticancer activities [29]. In addition, the 1-methyl-3-propyl-1H-pyrazole derivatives have shown their potential as anti-tubercular agents, as evidenced by their in vitro assessment [30]. Pyrazole is an active scaffold and a versatile lead molecule in pharmaceutical development and has interesting biological activity.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Molecular Modeling and Biological Evaluation of Novel Pyrazole Benzimidazolone Derivatives as Potent Antioxidants

Adardour,

Ait Lahcen,

Oubahmane

et al. 2023

Pharmaceuticals

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In the present study, we used benzimidazolone as a starting material to efficiently synthesize several hybrid compounds of pyrazole benzimidazolone derivatives by the 1,3-dipolar cycloaddition reaction. These compounds were obtained in average yields and were characterized by NMR (1H and 13C) and HRMS analysis. The antioxidant activity of the synthesized compounds 5(a–c) and 6(a–c) was evaluated using in vitro reduction assays, including ferric reducing antioxidant power (FRAP) and total antioxidant capacity (TAC). The results indicated that products 5c, 6b, and 6c exhibit higher antioxidant activity compared to the reference compounds and showed a remarkable ability to effectively remove the radical at IC50 (14.00 ± 0.14, 12.47± 0.02, and 12.82 ± 0.10 µM, respectively) under the TAC assessment. Conversely, compound 6c showed excellent activity at IC50 (68.97 ± 0.26 µM) in the FRAP assay. We carried out molecular docking and dynamics simulations to investigate the binding mode and stability of 5c, 6b, and 6c in the active site of human Peroxiredoxin 5. An ADMET study was conducted to determine the drug properties of the synthesized compounds.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Molecular Modeling and Biological Evaluation of Novel Pyrazole Benzimidazolone Derivatives as Potent Antioxidants

Adardour,

Ait Lahcen,

Oubahmane

et al. 2023

Pharmaceuticals

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Visible‐Light Induced Trifluoromethylation/Cyclization of Unactivated Alkene‐Bound Quinazolinones

Zou,

Zhao,

Wang

et al. 2024

Eur J Org Chem

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Herein, we reported a selective, mild method for the visible light‐photocatalyzed trifluoromethylation and cyclization of unactivated tethered alkenes to provide tri‐ and tetracyclic quinazolinones. Trifluoroacetic acid and anhydride are inexpensive and readily available reagents for the process which proceeds without the addition of a strong oxidant. Broad substrate scope and the formation of 5‐ and 6‐membered rings are demonstrated in 44‐82% yields. Control experiments provide the basis for a proposed mechanism involving photocatalyzed SET from fac‐Ir(ppy)3 to TFAA, and trifluoromethyl radical‐mediated regioselective cyclization. The practicality of the protocol was illustrated by a gram‐scale synthesis in 76% yield.

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Pyrazole-thiazole hybrids: Synthesis, computational studies and impact on digestive enzymes

Yadav,

Lakhia,

Bendi

et al. 2024

Journal of Molecular Structure

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One-pot sonochemical synthesis and in silico/in vitro antitubercular evaluation of 1-methyl-3-propyl-1H-pyrazole containing polynuclear fused N-heteroarenes

Cited by 4 publications

References 34 publications

Design, Synthesis, Molecular Modeling and Biological Evaluation of Novel Pyrazole Benzimidazolone Derivatives as Potent Antioxidants

Design, Synthesis, Molecular Modeling and Biological Evaluation of Novel Pyrazole Benzimidazolone Derivatives as Potent Antioxidants

Visible‐Light Induced Trifluoromethylation/Cyclization of Unactivated Alkene‐Bound Quinazolinones

Pyrazole-thiazole hybrids: Synthesis, computational studies and impact on digestive enzymes

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