General Aspects, Applications, and Recent Advancements of 1, 2-Disubstituted Benzimidazole Mannich Bases: A Privileged Scaffold

Babbar, Ritchu; Arora, Sandeep

doi:10.1149/10701.10631ecst

Cited by 3 publications

(2 citation statements)

References 13 publications

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“…[14] Incorporation of basic functional group via Mannich reaction renders the Mannich product very reactive and pharmacologically significant. Various reports from the literature revealed that Mannich bases possess antimicrobial, [15] anti-inflammatory, [16] analgesic, [17] anti-convulsant [18] activities etc.…”

Section: Introductionmentioning

confidence: 99%

Benzimidazol‐1‐yl‐1‐phenylpropanone Analogs as Potent Antimicrobial Agents: Rational Design and Synthesis

Babbar

Swikriti

Saini

et al. 2023

Chemistry & Biodiversity

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Designed, synthesized a sequence of novel benzimidazol‐1‐yl‐1‐phenylpropanone hybrids and assessed for in vitro antimicrobial potential counter to several bacterial strains. Computational Methodology was carried out for designing of the target molecules and structures were confirmed by spectroscopic analysis. Amid the 12 integrated derivatives, (3‐(2‐((3‐fluorobenzylidene)amino)‐1H‐benzo[d]imidazol‐1‐yl)‐1‐phenylpropan‐1‐one (6g) and 3‐(2‐((4‐fluorobenzylidene)amino)‐1H‐benzo[d]imidazol‐1‐yl)‐1‐phenylpropan‐1‐one (6k) were found to acquire excellent antibacterial activity against all bacterial strains (Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus), whereas derivative 3‐(2‐((2‐fluorobenzylidene)amino)‐1H‐benzo[d]imidazol‐1‐yl)‐1‐phenylpropan‐1‐one (6c), was potent against Escherichia coli, Bacillus subtilis, Staphylococcus aureus and displayed moderate action against P. aeruginosa. Derivatives with NO2 substituent at 3rd and 4th position, 3‐(2‐((3‐nitroobenzylidene)amino)‐1H‐benzo[d]imidazol‐1‐yl)‐1‐phenylpropan‐1‐one (6h) and 3‐(2‐((4‐nitroobenzylidene)amino)‐1H‐benzo[d]imidazol‐1‐yl)‐1‐phenylpropan‐1‐one (6 l) respectively declared good to moderate results against all bacterial strains. Further, 3‐(2‐((3‐chlorobenzylidene)amino)‐1H‐benzo[d]imidazol‐1‐yl)‐1‐phenylpropan‐1‐one (6f) and 3‐(2‐((4‐chlorobenzylidene)amino)‐1H‐benzo[d]imidazol‐1‐yl)‐1‐phenylpropan‐1‐one (6j) were found to be more competent against both fungal strains (C. albicans, A. niger). Serial two‐fold dilution method was used for the entire study and standard drugs utilized were ciprofloxacin and clotrimazole. MIC values (μg/ml) of novel synthesized analogs were reported in comparison to standard drugs for antibacterial and antifungal actions. Molecular docking studies showed that designed molecules dynamically bound with effective area of the receptor (DNA gyrase B, Clotrimazole complex of cytochrome P 45046A1) and in vitro results were in accord with in silico studies.

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Section: Introductionmentioning

confidence: 99%

Benzimidazol‐1‐yl‐1‐phenylpropanone Analogs as Potent Antimicrobial Agents: Rational Design and Synthesis

Babbar

Swikriti

Saini

et al. 2023

Chemistry & Biodiversity

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“…These compounds are known for their antiviral [10,11], anti-inflammatory [12][13][14], anticancer [15][16][17], antimicrobial [18][19][20], anti-HIV [21], anti-diabetes [22,23], and anticonvulsant [24] activities. Furthermore, benzimidazole compounds possess biological properties, including antioxidant activities [25][26][27].…”

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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Design and Synthesis of Neoteric Benzylidene Amino-Benzimidazole Scaffolds for Antioxidant and Anti-Inflammatory Activity

Swikriti

Babbar

Saini³

et al. 2023

Future Med. Chem.

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Aim: To design a series of neoteric benzylidene amino-benzimidazole derivatives and to synthesize and evaluate them for anti-inflammatory and antioxidant potential. Methods: The designed target scaffolds were synthesized and appraised for in vitro antioxidant action and in vivo anti-inflammatory potential. AutoDock Vina software was employed for design; the Mannich reaction was used for synthesis; and antioxidant and anti-inflammatory potential were demonstrated by the 2,2-diphenyl-1-picryl hydrazyl free-radical scavenging assay and carrageenan-induced paw edema method, respectively. Results: Methyl-incorporating molecules 3-(2-((2-methylbenzylidene)amino)-1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one (6c) and 3-(2-((4-methylbenzylidene)amino-1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one (6j) showed remarkable antioxidant and anti-inflammatory action, followed by compounds 6f, 6e and 6i containing 3-CH3, 2-OH, 4-F substituents, respectively. Conclusion: The designed analogs were dynamically confined within the active site of cyclooxygenase-2, and in vitro and in vivo results agreed with molecular docking studies.

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General Aspects, Applications, and Recent Advancements of 1, 2-Disubstituted Benzimidazole Mannich Bases: A Privileged Scaffold

Cited by 3 publications

References 13 publications

Benzimidazol‐1‐yl‐1‐phenylpropanone Analogs as Potent Antimicrobial Agents: Rational Design and Synthesis

Benzimidazol‐1‐yl‐1‐phenylpropanone Analogs as Potent Antimicrobial Agents: Rational Design and Synthesis

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

Design and Synthesis of Neoteric Benzylidene Amino-Benzimidazole Scaffolds for Antioxidant and Anti-Inflammatory Activity

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