Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against candida species

Göker, Hakan; Kuş, Canan; Boykin, David W.; Yıldız, Sulhiye; Altanlar, Nurten

doi:10.1016/s0968-0896(02)00103-7

Cited by 218 publications

(105 citation statements)

References 16 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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“…A variety of benzimidazoles are in used, like Thiabendazole, Flubendazole (antihelminthic), Omeprazole, Lansoprazole (anti-ulcerative) and Astemizole (anti-histaminic). The chemistry and pharmacology of benzimidazoles have been of great interest to medicinal chemistry [7,8] , because of its derivatives possessed various biological activities such as anti-oxidant [9,10], anti-microbial [11][12][13][14][15][16] , antihelmentic [17][18][19], anti-cancer [20], anti-hypertensive [21], anti-neoplastic [22], anti-inflammatory [23,24], analgesic [25], anti-protozoal [26,27], anti hepatitis activities [28] and also shows anti-depressant activity [29].…”

Section: Introductionmentioning

confidence: 99%

A novel approach to synthesis of flibanserin

Reddy¹,

Mukkanti²,

Rao³

2016

Int. J. Curr. Res. Chem. Pharm. Sci

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The 1,3-dihydro-1-(2-bromoethyl)-3-isopropenyl-2H-benzimidazol-2-one was used as a starting material for making of the title compound. This compound treated with piperizine in the presence of TBAB as a catalyst which is treated with m-trifluoromethyl bromobenzene, in the presence of base and palladium acetate than followed by passing HCl gas to produced corresponding title compound in good yield with high purity. The structures of all the synthesized compounds were confirmed by IR, 1 H NMR, C 13NMR and Mass Spectral data.

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“…Both heteroatoms are nitrogen (N), which are present at non-adjacent position [3]. The benzimidazole moiety is an important heterocyclic ring, a wide variety of benzimidazole derivatives are known for their chemotherapeutic importance and antimicrobial activities [4][5][6][7][8][9], antifungal activity [10][11][12], anti-inflammatory [13] and antioxidant [14][15][16][17][18] in this context. Due to great potential of the moiety, synthesis of benzimidazole derivatives was carried out to evaluate their antimicrobial.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and antibacterial evaluation of some novel derivatives of 2-bromomethyl-benzimidazole

Ahmadi¹

2014

Bull. Chem. Soc. Eth.

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ABSTRACT. In the present study, synthesis, and biological evaluation of some novel derivatives of 2-bromomethyl-benzimidazole were investigated. The structures of the new synthesized compounds were characterized by IR, 1 H-NMR, 13 C-NMR, mass spectrometry and elemental analysis and screened for antimicrobial activity against two Gram-positive strains (Staphylococcus aureus and Bacillus subtilis) and two Gram-negative strains (Escherichia coli and Pseudomonas aeruginosa). Results indicate that new compounds showed moderate to good activity when compared with standard antibiotic Ciprofloxacin and Streptomycin.

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Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against candida species

Cited by 218 publications

References 16 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

A novel approach to synthesis of flibanserin

Synthesis, characterization and antibacterial evaluation of some novel derivatives of 2-bromomethyl-benzimidazole

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