Efficient and simple synthesis of novel 1,2,3-triazolyl-linked benzimidazolone, molecular docking and evaluation of their antimicrobial activity

Adardour, Mohamed; Boutafda, Aziz; Hdoufane, Ismail; Aghraz, Abdellah; Hafidi, Mohamed; Zaballos-García, Elena; Cherqaoui, Driss; Baouid, A.

doi:10.1080/00397911.2020.1803913

Cited by 15 publications

(4 citation statements)

References 34 publications

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“…Continuing our previous investigations on the synthesis of benzimidazolone derivatives, we report the synthesis of 1-(cyclohex-1-en-1-yl)-3-(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazol-2-one (2) in one step using a direct alkylation reaction under phase-transfer catalysis conditions (Scheme 1). The title compound (2) was synthesized through the direct N-alkylation of benzimidazolone 1 using a previously described process [18,22]. Compound 1 was reacted with propargyl bromide which acted as a catalyst.…”

Section: Synthesis and Structural Characterizationmentioning

confidence: 99%

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Crystal Structure, DFT Calculation, and Hirshfeld Surface Analysis of the 1-(Cyclohex-1-en-1-yl)-3-(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazol-2-one

Adardour,

Ait Lahcen,

Hdoufane

et al. 2023

Crystals

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In this paper, we describe the synthesis and structural characterization of the 1-(cyclohex-1-en-1-yl)-3-(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazol-2-one (2) via IR, NMR (1H and 13C), and HRMS. The crystal structure of the isolated organic compound 2 was confirmed through single-crystal X-ray diffraction analysis. The experimental results regarding the molecular geometry and intermolecular interactions within the crystal are in accordance with the DFT calculations and Hirshfeld surface analysis.

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Section: Synthesis and Structural Characterizationmentioning

confidence: 99%

“…The solvent was evaporated under vacuum, and the residue was purified using column chromatography on silica gel using a hexane/ethyl acetate mixture (8/2) as eluent. This procedure made it possible to obtain a pure and isolated product with a yield of 85% [22].…”

Section: Synthesis Of Alkylated Benzimidazolones (2)mentioning

confidence: 99%

Crystal Structure, DFT Calculation, and Hirshfeld Surface Analysis of the 1-(Cyclohex-1-en-1-yl)-3-(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazol-2-one

Adardour,

Ait Lahcen,

Hdoufane

et al. 2023

Crystals

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“…Continuing our previous works concerning synthesizing new heterocyclic systems [54][55][56], we are interested in preparing new heterocyclic systems containing benzimidazolone rings. To this end, we have prepared the dipoles and the alkylated benzimidazolones, and the latter have dipolarophilic sites that can react with the synthesized nitrilimines.…”

Section: Chemistrymentioning

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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“…Nitrogen-containing compounds such as glutaramides, 1 piperidino[1,2- a ]benzimidazol-1-ones 2 and N -cyclopentenyl benzimidazolones 3 exist in a wide range of biologically important natural products and synthetic molecules. In addition, they also serve as important building blocks in organic synthesis.…”

mentioning

confidence: 99%

Green synthesis of glutaramides, piperidino[1,2-a]benzimidazol-1-ones and N-cyclopentenyl benzimidazolones enabled by microwave assisted domino reactions of cyclic 2-diazo-1,3-diketones with aniline derivatives

Zhao,

Hu,

et al. 2024

Org. Chem. Front.

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Efficient and simple synthesis of novel 1,2,3-triazolyl-linked benzimidazolone, molecular docking and evaluation of their antimicrobial activity

Cited by 15 publications

References 34 publications

Crystal Structure, DFT Calculation, and Hirshfeld Surface Analysis of the 1-(Cyclohex-1-en-1-yl)-3-(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazol-2-one

Crystal Structure, DFT Calculation, and Hirshfeld Surface Analysis of the 1-(Cyclohex-1-en-1-yl)-3-(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazol-2-one

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

Green synthesis of glutaramides, piperidino[1,2-a]benzimidazol-1-ones and N-cyclopentenyl benzimidazolones enabled by microwave assisted domino reactions of cyclic 2-diazo-1,3-diketones with aniline derivatives

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