Synthesis and in vitro antimicrobial activity of some novel substituted benzimidazole derivatives having potent activity against MRSA

Tunçbìlek, Meral; Kiper, Tuluğ; Altanlar, Nurten

doi:10.1016/j.ejmech.2008.06.026

Cited by 121 publications

(87 citation statements)

References 40 publications

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“…This great attention is essentially due to their wide range of biopharmacological activities including antihelminthic [1], antitumoral [2], antimicrobial [3], antifungal [4], antiviral [5], antihistaminic and antiallergic [6] properties. The benzimidazole derivatives showed to be also excellent inhibitors of HIV-1 reverse transcriptase [7].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1-(1H-benzimidazol-2-yl)-3- (3-nitrophenyl)prop-2-en-1-one, C16H11N3O3

Bisseyou¹,

Guillot²,

Sissouma³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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C 16 H 11 N 3 O 3 ,monoclinic, P12 1 /c1(no. 14), a =9.3959(2) Å, b =5.7085(1) Å, c =24.8921(7) Å, b =96.885(1)°, V =1325.5 Å 3 , Z =4,Rgt(F) =0.041, wRref(F 2 ) =0.152, T =100 K.Source of material 2-Acetylbenzimidazole (1.5 g, 10 mmol) was dissolved to asolution of EtOH (40 ml) and 3g(75 mmol) of NaOH. To this solution, 10 mmol of 3-nitrobenzaldehyde was added. The mixture was stirred at ambient temperature during 5h.The resulting mixture was neutralized with a4Nsolution of HCl. The precipitate was dried and recrystallized from amixture of toluene/EtOH (4 : 1, v/v)(yield 68 %, m.p. >533 K). Yellow crystals of parallelepiped shape suitable for single-crystal diffraction were grown by slow evaporation at ambient temperature and in air from ahot solution in acetonitrile. NMR data are available in the CIF. Experimental details DiscussionBenzimidazole and its derivatives constitute one of the most extensively studied families of organic compounds in regard to the number of articles published on these compounds. This great attention is essentially due to their wide range of biopharmacological activities including antihelminthic [6] properties. The benzimidazole derivatives showed to be also excellent inhibitors of HIV-1 reverse transcriptase [7]. The benzimidazole nucleus system, whose inestimable virtues seduced the scientific community, was moreover classified as an important pharmacophore in the discovery of modern drug [8]. From this point of view, the benzimidazole nucleus system constitutes abasic molecular scaffold in the design of new molecules of pharmacological interest. The title molecular structure consists of three main parts: the benzimidazole ring and the nitrophenyl ring related by enone group (figure, top). In the benzimidazole ring the bond lengths and angles are in good agreement with those observed in the 1-(1H-benzimidazol-2-yl)-3-(3-chlorophenyl)-prop-2-en-1-one [9]. The C10=N2 double bond and C16-N2 single bond in the imidazole ring are clearly distinguishable with bond lengths of 1.323(2) and 1.387(1) Å,r espectively. The benzimidazole ring makes dihedral angles of 2.66(3)°and 1.16(3)°with phenyl ring and mean plane of enone group, respectively. It confers to the molecule an almost planar structure. The magnitudes of structural parameters of phenyl ring are within normal ranges [10], with a light opening of intramolecular angle at C4 atom due to the presence of nitro group which is twisted of 13°with respect of phenyl ring. The N3-O2 and N3-O3 bonds of nitro group have similar distances of 1.226 (2)

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 1-(1H-benzimidazol-2-yl)-3- (3-nitrophenyl)prop-2-en-1-one, C16H11N3O3

Bisseyou¹,

Guillot²,

Sissouma³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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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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“…The benzimidazole has been an important pharmacophore and privileged structure, encompassing a diverse range of their biological properties [1,2]. Benzimidazoles have been reported as antimicrobial [3][4][5][6][7][8][9][10], antiviral [11][12][13][14], antioxidant [15], anti-inflammatory [16,17], antitumor [18] and anticancer agents [19][20][21]. 1,2,3-Triazoles due to their exclusive chemical and structural properties, have acknowledged a lot of awareness over the past decades and found extensive applications in medicinal chemistry [22][23][24][25], biological activities such as anti-HIV [27] and antimicrobial [27,28].…”

Section: Introductionmentioning

confidence: 99%

One pot synthesis of 1-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-1H-benzo[d] imidazoles in ionic liquids: Evaluation of antioxidant and antimicrobial activities

et al. 2015

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Synthesis and in vitro antimicrobial activity of some novel substituted benzimidazole derivatives having potent activity against MRSA

Cited by 121 publications

References 40 publications

Crystal structure of 1-(1H-benzimidazol-2-yl)-3- (3-nitrophenyl)prop-2-en-1-one, C16H11N3O3

Crystal structure of 1-(1H-benzimidazol-2-yl)-3- (3-nitrophenyl)prop-2-en-1-one, C16H11N3O3

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

One pot synthesis of 1-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-1H-benzo[d] imidazoles in ionic liquids: Evaluation of antioxidant and antimicrobial activities

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