Synthesis, Characterization and Molecular Docking Studies of Novel N-(benzimidazol-1-ylmethyl)-4-chlorobenzamide Analogues for Potential Anti-inflammatory and Antimicrobial Activity

Sethi, R. K.; Jain, Sandeep; Arora, Sandeep; Saini, Deepika; Jain, Neelam

doi:10.2174/1871523017666180426125141

Cited by 7 publications

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“…In the light of the above obtained findings and in continuation with our previous research work [19,20] we hereby announce, design, construction, and antimicrobial assessment of novel benzoimidazol‐1‐yl‐1‐phenylpropanone analogs prepared via Mannich reaction. Structures were elucidated by spectral and elemental analysis.…”

Section: Introductionsupporting

confidence: 63%

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: Introductionsupporting

confidence: 63%

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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“…The most potent compound among the produced derivatives was determined to be derivative (17) N-[2-(2chloro-phenyl)-benzimidazol-1-ylmethy]-4-chlorobenzam, which has a 2-chlorophenyl moiety at position 2 on the benzimidazole scaffold. 24 The structure of the compound possessing antimicrobial activity is given in Figures 1 and 2.…”

Section: Antimicrobial Activity Of Mannich Basesmentioning

confidence: 99%

Recent advances in biological applications of mannich bases — An overview

Raju

Vengadhajalaphathy²,

Sundaram³

et al. 2023

IJPCA

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Mannich bases are beta-amino ketone-carrying compounds that are the end products of the Mannich reaction. The Mannich reaction is essential in the synthesis of nitrogen-containing compounds. The Mannich reaction, a nucleophilic addition reaction that forms carbon-carbon bonds, is employed in the synthesis of numerous natural products, drugs and other compounds. There are several aminoalkyl chain bearing Mannich bases with high curative value, such as fluoxetine, atropine, ethacrynic acid, trihexyphenidyl, and many others. According to the literature, Mannich bases are highly reactive and have been demonstrated to have powerful anti-inflammatory, anticancer, antifilarial, antibacterial, antifungal, anticonvulsant, anthelmintic, antitubercular, analgesic, anti-HIV, antimalarial, antipsychotic, antiviral, antilipase activity and other properties. The primary source of, -α,β-unsaturated ketone, which can be produced by deaminating the hydrogen atom of the amine group, is responsible for the biological action of Mannich bases. However, a number of minor biological functions of Mannich bases have been reported, including their ability to control blood pressure or prevent platelet aggregation, their impact on parasites and ulcers, and their use as medications for mental health issues. Since there is a greater need for anticonvulsant pharmaceuticals, these anticonvulsant medications containing N-mannich base groups will exhibit an increase in lipophilic nature and hence have improved blood-brain barrier penetration. The overview concludes with a brief explanation of the potential of Mannich bases as inhibitors of various enzymes or ligands for various receptors.

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“…In silico studies were also done to show the linkage of the target compounds with protein of microbe. It was found that derivative (8) was found to be the most suitable antimicrobial compound among the manufactured derivatives (Sethi et al, 2018).…”

Section: Anti-fungal Activitymentioning

confidence: 99%

A Comprehensive Review on Therapeutic Potential of Benzimidazole: A Miracle Scaffold

Babbar

Swikriti

Arora

2020

JPTRM

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Background: Benzimidazole is a category of heterocyclic aromatic compounds formed from the fusion of six membered benzene with five membered imidazolering. The moiety possesses diverse biological and clinical applications. A number of studies have shown that a varied substituent around the benzimidazole nucleus results in pharmacologically active compounds of therapeutic interest. Purpose: Owing to its number of pharmacological properties, this moiety is of choice of interest in designing and synthesis of new therapeutic compounds. The existence of the benzimidazole core in numerous groups of biological agents like antimicrobial, antiviral, antiparasitic, antihypertensive, anticancer, CNS stimulant as well as depressants has made important scaffold for development of many newer therapeutic agents. There is utmost need to understand the synthesis and associated role of benzimidazole derived compounds in different diseases. Therefore, in the present review, we attempt to discuss various derivatives of benzimidazole nucleus with different pharmacological activities. Conclusion: Benzimidazoles have played a great role in discovery of drug and development. Huge attempt has been made towards benzimidazole heterocyclic-based organic compounds with great excellence that resulted in drugs with enormous biological activity. Therapeutic drugs containing benzimidazole nucleus are used in building drugs that serve to be an active area of research. This article becomes a source that will lead to discovery of new opportunities for all researchers interested in benzimidazole-based heterocyclic medicinal chemistry.

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Synthesis, Characterization and Molecular Docking Studies of Novel N-(benzimidazol-1-ylmethyl)-4-chlorobenzamide Analogues for Potential Anti-inflammatory and Antimicrobial Activity

Abstract: These results designate that N-(Benzimidazol-1-ylmethyl)-4-chlorobenzamide analogues, substituted with halogen functionality, could be used as potential lead for designing more potent anti-inflammatory and antimicrobial agents.

Cited by 7 publications

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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

Recent advances in biological applications of mannich bases — An overview

A Comprehensive Review on Therapeutic Potential of Benzimidazole: A Miracle Scaffold

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