Benzimidazole: An important Scaffold in Drug Discovery

Preethi, P. Jaya; Karthikeyan, E.; Lohita, M.; Teja, P. Goutham; Subhash, M. N.; Shaheena, P.; Prashanth, Y.; Sai, Nandhu K.

doi:10.5958/2231-5713.2015.00021.5

Cited by 14 publications

(11 citation statements)

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“…All chemical shift (δ) values are expressed in ppm. The purities of the compounds were checked by thin layer chromatography (TLC) on silica gel-G plates.Numerous methods are available for the synthesis of benzimidazole derivatives [14,16,17]. A simple method was applied for the synthesis of our target compounds.…”

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confidence: 99%

“…Therefore benzimidazole has drawn considerable interest as an important scaffold in drug discovery [14]. However, many of the activities of benzimidazole derivatives have not been extensively investigated like antioxidant activity.…”

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confidence: 99%

“…Numerous methods are available for the synthesis of benzimidazole derivatives [14,16,17]. A simple method was applied for the synthesis of our target compounds.…”

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confidence: 99%

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Synthesis and Antioxidant Activity of 2-Substituted-5-Nitro Benzimidazole Derivatives

Das

Hossain

Kumar

et al. 2016

Int J Pharm Pharm Sci

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Objective: This study was conducted to synthesise some 2-substituted-5-nitro benzimidazole derivatives to evaluate their antioxidant activity. Methods:The titled compounds were synthesised by sodium metabisulfite mediated reaction of 4-nitro-1, 2-phenylenediamine with a number of para-substituted benzaldehydes. The antioxidant activity was evaluated by 2, 2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging method. Results: All the compounds exhibited good antioxidant activity having IC50Conclusion: Among the synthesised compounds, compounds 3a-c have been found to possess the most prominent antioxidant activity which might be attributed due to the presence of chloro, bromo and fluoro substituents in the molecule. The compounds may act as the future lead(s) for the development of potential antioxidant compounds.values in the range of 3.17 to 7.59 µg/ml while that of standard butylated hydroxytoluene (BHT) was 18.42 µg/ml. [10] activity. A Recent report shows that two groups of substituted benzimidazoles, namely 5, 6-dinitro and 2-trifluoromethylderivatives are the promising candidates for antimicrobial drugs [11,12]. Besides 2-mercapto-benzimdiazole compounds have been reported to have significant antimicrobial properties [13]. KeywordsTherefore benzimidazole has drawn considerable interest as an important scaffold in drug discovery [14]. However, many of the activities of benzimidazole derivatives have not been extensively investigated like antioxidant activity. But the compounds having antioxidant and free radical scavenging properties are considered to be used for the prevention or treatment of human diseases like neurodegenerative disorders, atherosclerosis, rheumatoid arthritis and carcinogenesis, because oxygen-derived free radicals such as superoxide (O2 The major reagents for synthesis were purchased from SigmaAldrich Chemical Corporation and were used after being purified by standard procedures. The other chemicals used were of reagent/analytical grade. Melting points were determined by open capillary method with the help of WRS-1B (Germany) digital melting point apparatus and are uncorrected. All the reactions were monitored by TLC on silica gel thin layer plates. UV data were taken using Shimadzu UV-166V spectrophotometer. IR spectra were recorded by using the KBr disk on Shimadzu IR-470 spectrophotometer..-), nitric oxide (NO.), hydroxyl (OH.) and peroxy (ROO.) play an important role in causing these diseases [15]. Nsubstituted benzimidazole derivatives and 2-aryl substituted benzimidazole and benzothiazole derivatives have recently been reported to show significant antioxidant activity [16,17]. Taking in mind all these recent observations regarding biological activities of benzimidazole derivatives we became interested in synthesising 2-substituted benzimidazole derivatives in order to investigate their anti-oxidant activity. In the present study, we had studied the antioxidant activity of 2-substituted-5-nitro benzimidazole derivatives 3 (scheme 1) and we herein report the results of...

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Synthesis and Antioxidant Activity of 2-Substituted-5-Nitro Benzimidazole Derivatives

Das

Hossain

Kumar

et al. 2016

Int J Pharm Pharm Sci

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“…[36] Therefore benzimidazole has drawn significant interest as an important scaffold in drug discovery. [37] Commonly benzimidazole prepared through condensation of different carboxylic acid derivatives with orthoaminoanilines. [38,39] However, some disadvantages of these conditions are always associated such as longer reaction time, availability of the starting materials, lower product yields, expensive catalysts, and high temperature.…”

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“…[ 36 ] Therefore benzimidazole has drawn significant interest as an important scaffold in drug discovery. [ 37 ]…”

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Microwave assisted synthesis, biological activities, and in silico investigation of some benzimidazole derivatives

Bhavsar

Acharya

Jethava

et al. 2020

Journal of Heterocyclic Chem

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Some derivatives of 2-substituted benzimidazole were prepared via coupling of N-methyl-o-phenylenediamine or o-phenylenediamine with different aromatic aldehydes catalyzed by Ni(OAc) 2 in the presence of chloroform under microwave-assisted conditions. Structural confirmation of all synthesized molecules was investigated by FT-IR, 13 C NMR, 1 H NMR, ESI-MS, and Elemental analysis. All prepared molecules were examined for in-vitro pharmaceutical activities like antibacterial, antifungal, antimalarial, antituberculosis, and antioxidant. Additionally, in silico study was also carried out. We also evaluated the steadiness and molecular interaction of docked complex, that is, complex of molecule (7s) with PDB: 5ZNI and complex of derivative (7l) with PDB: 3VLN, we have established a molecular dynamics model on the best dock molecules. All newly prepared molecules were authenticated to have excellent pharmacokinetics stuffs via calculated ADME-Tox descriptors, which signifying that these derivatives could be utilized as hit for the expansion of the some innovative active compounds.

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One‐pot synthesis of novel benzimidazoles with a naphthalene moiety as antimicrobial agents and molecular docking studies

Ersan

Yüksel

Ertan-Bolelli

et al. 2020

J Chinese Chemical Soc

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In an attempt to design a greener approach for the synthesis of a potent class of antimicrobials, 1,2‐phenylenediamine derivatives were reacted with various 1/2‐carboxylic acid‐substituted naphthalene derivatives to generate a series of naphthyl‐substituted benzimidazole derivatives (11–19) using polyphosphoric acid as catalyst under microwave irradiation and conventional synthesis method. This is an eco‐friendly and swift reaction method for a synthetic approach to diverse benzimidazoles. Structures of the synthesized compounds were established on the basis of spectral data and they were screened for their antimicrobial activity. Compound 18 showed maximum potency against all Gram‐positive and Gram‐negative bacterial strains with a minimum inhibitory concentration (MIC) value in the range of 7.81–62.50 μg/ml. Only compound 17 was found to be the most active against all fungal strains with a MIC value of 15.62 μg/ml. In this study, we performed molecular docking experiments to understand the interactions between compounds 17 and 18 and E. coli topoisomerase I, and we compared the results obtained with that of 2‐(3,4‐dimethoxyphenyl)‐5‐[5‐(4‐methylpiperazin−1‐yl)‐1H‐benzimidazol‐2‐yl]‐1H‐benzimidazole (DMA). Compounds 17 and 18 demonstrated strong interactions with important active site residues, similar to DMA. As a result, the compounds obtained from this study can be used in designing new potent inhibitors of E. coli topoisomerase I.

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Benzimidazole: An important Scaffold in Drug Discovery

Cited by 14 publications

References 0 publications

Synthesis and Antioxidant Activity of 2-Substituted-5-Nitro Benzimidazole Derivatives

Synthesis and Antioxidant Activity of 2-Substituted-5-Nitro Benzimidazole Derivatives

Microwave assisted synthesis, biological activities, and in silico investigation of some benzimidazole derivatives

One‐pot synthesis of novel benzimidazoles with a naphthalene moiety as antimicrobial agents and molecular docking studies

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