A green and convenient approach toward benzimidazole derivatives and their antimicrobial activity

Wen, Jing; Luo, Yun-Lei; Zhang, Huizhen; Zhao, Huanhuan; Zhou, Cheng‐He; Cai, Gui‐Xin

doi:10.1016/j.cclet.2015.12.014

Cited by 19 publications

(11 citation statements)

References 39 publications

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“…The benzimidazole derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were synthesized according to Scheme 1 and characterized by physicochemical and spectral means. The spectral data of the synthesized compounds is found in agreement with the assigned molecular structures.…”

Section: Chemistrymentioning

confidence: 99%

“…Benzimidazole, also known as benzoglyoxaline, is a heterocyclic moiety of choice for the researchers in modern times [13]. The presence of imidazole (a biologically active pharmacophore) makes it a versatile heterocycle with an extensive range of biological activities such as antihistaminic [14], antiulcer, antitubercular [15], antioxidant [16], anti-HIV [17], anti-inflammatory [18], analgesic [19], antimicrobial [20], antiprotozoal, antitrichinellosis [21], antihypertensive [22], anticancer [23] DNA binding [24] and antimicrobial activities [25].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and evaluation of antimicrobial, antitubercular and anticancer activities of benzimidazole derivatives

Yadav

Narasimhan

Lim

et al. 2018

Egyptian Journal of Basic and Applied Sciences

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A series of benzimidazole derivatives (1-20) was synthesized and evaluated for its in vitro antimicrobial, antitubercular and anticancer activities. Compound 10 was found to be the most active antibacterial agent. The compounds active in in vitro evaluation against M. tuberculosis were further assessed for their in vivo activity in mice and for their capacity to inhibit the vital mycobacterial enzymes viz., isocitrate lyase, pantothenate synthetase and chorismate mutase. The dose of the compounds in antitubercular evaluation that proved fatal and highly toxic to mice was 5.67 mg/kg while lethal dose varied from 1.82 mg/kg to 3.23 mg/kg body weight of the mice. A dose of 1.34 mg/kg was found to be safe for each of the compounds. All compounds inhibited the mycobacterial enzymes but to a lesser extent than streptomycin sulphate used as positive control. Compound 19, exhibiting inhibition of 67.56%, 53.45%, and 47.56% against isocitrate lyase, pantothenate synthetase and chorismate mutase, respectively is the most potent antitubercular compound among the synthesized benzimidazole derivatives. Further, compound 19 also emerged as a potent anticancer agent (IC 50 = 0.0013 mM) than 5-flourouracil against breast cancer cell line (MCF 7).

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Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of antimicrobial, antitubercular and anticancer activities of benzimidazole derivatives

Yadav

Narasimhan

Lim

et al. 2018

Egyptian Journal of Basic and Applied Sciences

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“…Nitrogen-containing compounds are an important class of organic molecules and building blocks widely found in natural products, drug molecules, and functional materials. − Consequently, much effort has been devoted for their efficient syntheses, especially for the formation of diverse C–N bonds. − Among the methods developed, aza-Michael addition reactions prove to be one of the simplest and most effective approaches to the corresponding adducts, such as β-amino sulfone, β-amino nitrile, or β-amino carbonyl products, from readily available starting materials and with high atom- and step-economic character. − Since the poor nucleophilicity of aromatic aza-heteroarenes and aromatic amines, − the aza-Michael addition reactions are predominately limited to aliphatic amines. As a result, strong acidic or basic conditions, elevated reaction temperature or long reaction time are frequently utilized to promote the aza-Michael addition reactions of aromatic aza-heteroarenes and Ts-protected amines (Scheme , top). − These harsh conditions are not compatible to substrates containing acid- or base-sensitive functionalities.…”

Section: Introductionmentioning

confidence: 99%

Transition Metal- and Base-Free Electrochemical aza-Michael Addition of Aromatic aza-Heterocycles or Ts-Protected Amines to α,β-Unsaturated Alkenes Mediated by NaI

Sun

Zeng

2018

ACS Sustainable Chem. Eng.

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A highly efficient and mild electrochemical protocol has been developed for the aza-Michael addition of aromatic aza-heterocycles or Ts-protected amines with α,β-unsaturated alkenes to give corresponding β-amino sulfone, β-amino nitrile, β-amino ester, and β-amino ketone in moderate to excellent yields. The chemistry proceeded using NaI as a redox mediator in an undivided cell at ambient temperature. Unlike the conventional aza-Michael additions, the utilization of strong acid, base, or transition metal-based catalysts is circumvented. In addition, it was observed the electrochemically in-situ-generated molecular iodine has higher activity than that under nonelectrochemical reaction conditions.

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“…Benzimidazole is an important pharmacophore and privileged structure in the field of medicinal chemistry because of its varied biological activities, viz., anticancer [8,9], antihypertensive [10,11], antiviral [12,13], anti-inflammatory [14,15], antihistaminic [16,17], antiulcer [18], anticoagulant [19,20], and antimicrobial [21,22]. The antimicrobial action of benzimidazole is due to its structural similarity to purines; therefore, its derivatives inhibit nucleic acid and protein synthesis by competing with natural purines; thereby inhibit the growth as well as kill bacterial strains [23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and in Vitro Antimicrobial Evaluation of Some Novel Benzimidazole Derivatives Bearing Hydrazone Moiety

Sarma

Singh

Gupta

et al. 2017

Asian J Pharm Clin Res

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Objective: The synthesis of novel benzimidazole-hydrazone derivatives has been carried out based on the previous findings that both these pharmacophores possess potent antimicrobial activities. The antibacterial properties of synthesized derivatives were screened against both Grampositive and Gram-negative bacteria.Methods: O-phenylenediamine on condensation with substituted aromatic acids in polyphosphoric acid gave benzimidazole nucleus which on reaction with ethyl chloroacetate and hydrazine hydrate in two different steps resulted in the formation of substituted acetohydrazides. The targeted compounds 6a-l were synthesized by reaction of substituted acetohydrazides with aromatic aldehydes and screened for their antibacterial potential by cup-plate method. Results:The synthesized benzimidazole-hydrazones exhibited moderate to strong antibacterial activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa. The compounds 6a-6f were found to be most effective against S. aureus, E. coli, and P. aeruginosa. Among all the synthesized compounds, the zone of inhibition of 6f in highest concentration, i.e., 100 µg/ml were found to be >31 mm against all the stains of bacteria. Conclusion:The antibacterial results revealed that the synthetized derivatives have significant antimicrobial properties and further structure activity relationship studies may develop more potent and less toxic molecules.

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A green and convenient approach toward benzimidazole derivatives and their antimicrobial activity

Cited by 19 publications

References 39 publications

Synthesis and evaluation of antimicrobial, antitubercular and anticancer activities of benzimidazole derivatives

Synthesis and evaluation of antimicrobial, antitubercular and anticancer activities of benzimidazole derivatives

Transition Metal- and Base-Free Electrochemical aza-Michael Addition of Aromatic aza-Heterocycles or Ts-Protected Amines to α,β-Unsaturated Alkenes Mediated by NaI

Synthesis, Characterization and in Vitro Antimicrobial Evaluation of Some Novel Benzimidazole Derivatives Bearing Hydrazone Moiety

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