Novel benzimidazolium salts and their silver complexes: Synthesis and antibacterial properties

Günal, Selamı; Kaloğlu, Nazan; Özdemır, İlknur; Demır, Serpıl; Özdemır, İsmaıl

doi:10.1016/j.inoche.2012.04.033

Cited by 64 publications

(18 citation statements)

References 45 publications

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“…In this area, many articles have been recently published on the synthesis and applications of silver–NHC complexes. Recently we reported the bioorganometallic studies by silver and gold complexes of imidazolin‐2‐ylidene and benzimidazol‐2‐ylidene ligands for antimicrobial applications …”

Section: Introductionmentioning

confidence: 99%

Silver–N‐Heterocyclic Carbene Complexes: Synthesis, Characterization, and Antimicrobial Properties

Kaloğlu

Özdemır

et al. 2017

J Chinese Chemical Soc

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Six new silver complexes containing symmetrical N‐heterocyclic carbene (NHC) ligands were synthesized by the reaction of azolium salts with Ag2O in CH2Cl2 . These complexes were tested against Gram‐negative bacterial strains (Escherichia coli and Pseudomonas aeruginosa), Gram‐positive bacterial strains (Enterococcus faecalis and Staphylococcus aureus), and fungal strains (Candida albicans and Candida tropicalis), and all tested complexes showed good activity against the different microorganisms.

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Section: Introductionmentioning

confidence: 99%

Silver–N‐Heterocyclic Carbene Complexes: Synthesis, Characterization, and Antimicrobial Properties

Kaloğlu

Özdemır

et al. 2017

J Chinese Chemical Soc

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“…Thermal stabilities of the symmetrical and unsymmetrical dicationic ILs are higher than their corresponding conventional monocationic ILs. [20][21][22][23][24] Their antibacterial and antifungal effects are attributed to cationic interactions with negatively charged parts of bacterial membranes. 7,9 Thermogravimetric analysis (TGA) at elevated temperatures is used to evaluate thermal stability of many dicationic ILs.…”

Section: Introductionmentioning

confidence: 99%

Bis-imidazolium and benzimidazolium based gemini-type ionic liquids structure: synthesis and antibacterial evaluation

2015

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Based on bis-imidazolium and benzimidazolium, new sets of geminal dicationic ionic liquids containing sulphonamide moiety were successfully synthesized with good yields. Their structures were confirmed by 1 H-NMR, 13 C-NMR, FT-IR, and mass spectroscopy. Selected physicochemical properties of these ILs including; thermal stability by TGA and miscibility in some common organic solvents and water were also determined. Most of the prepared dicationic ILs displayed significant level of antibacterial activities against ten selected bacterial strains of Gram-positive and Gram-negative using micro-broth dilution assay. ͞ calcd. for C 29 H 42 N 5 O 6 S 3+ : 588.2856, found: 588.2919; m/z, [NTF 2 ] ͞ calcd. for C 2 F 6 NO 4 S 2 − : 279.9173, found: 279.9145. N,N-bis[(3-allyl-benzimidazol-1-iumyl)ethyl]-4-methylbenzenesulphonamide-bis(trifluorometh- ylsulphonyl)amide (8a)This compound was prepared analogously to 7d using N, N-bis[(3-allyl-benzimidazol-1-iumyl) ethyl]-4-methylbenzenesulphonamide bromide 6a (0.7 g, 1.0 mmole) and Lithium bis-(trifluoromethanesulphonyl)imide LiNTf 2 (0.72 g, 2.5 mmol) to provide a clear viscous hygroscopic liquid at room temperature in 90% yield (1 g). Ten standard strains of Gram positive and negative bacteria were used to evaluate the antibacterial activities of the synthesized ILs compounds; 5a-f and 6a-f. Based on CLSI guidelines 85 , the activities were assessed in terms of minimum inhibitory concentrations (MICs) using microbroth dilution assays. The MIC's values are given in mg/mL and defined as a lowest concentration that inhibits the bacterial strains growth. Gram positive bacteria included: Streptococcus pyogenes ATCC19615, Staphylococcus aureus ATCC 29213, Bacillus subtilis ATCC6051, Rodococcus Ruber ATCC27863, Enterococcus faecalis ATCC 29212, Staphylococcus epidermidis ATCC12228, while Gram negative bacteria included: Escherichia coli ATCC10538, Salmonella typhimurium ATCC14028, Pseudomonas aeruginosa ATCC15442, Acinetobacter calcoaceticus ATCC 23055. These standards strains were obtained from the collection Distilled water was used as negative control to dissolve all the tested ILs in concentrations range of 0.05-0.5 mg/mL, while, commercial antibiotics amoxicillin and kanamycin were used as a positive control in the same range of concentrations. A loopful of bacterial cells from the nutrient agar plates ofThe incorporated benzenesulfonamide moiety and the active side substituents into diimidazolium and benzimidazolium cations enhanced both antibacterial activity and miscibility for the synthesized gimini type ILs.

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“…Compounds 2 – 22 were prepared according to previously published procedures . Benzimidazole (1 mmol) was dissolved in 20 mL of ethanol.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and In Vitro Anticancer Evaluation of Some Benzimidazolium Salts

Akkoç

Kayser

2019

Journal of Heterocyclic Chem

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A series of benzimidazolium salts having 2‐cyanobenzyl (2–6), 2‐(4‐nitrophenyl)ethyl (7–10), (1,3‐dioxoisoindolin‐2‐yl)butyl (11–17) or N‐methylphthalimide (18–22) substitution were synthesized and characterized by spectroscopic and analytical techniques. The in vitro cytotoxic activity of these salts was tested against human colon cancer (DLD‐1), human breast cancer (MDA‐MB‐231), and normal human noncancerous embryonic kidney (HEK‐293T) cell lines using the MTT assay method. The viability rates of the cells were determined by confocal microscopy. The majority of the newly synthesized compounds, with the exception of compounds 2, 3, 8, 11, 12, and 17, displayed high cytotoxic activity against cancerous cells. In fact, compounds 6 and 7 exhibited better results than the positive control drugs, cisplatin and busulfan, against the MDA‐MB‐231 cells. Therefore, compounds 6 and 7 could be considered as anticancer drug candidates for further development.

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Novel benzimidazolium salts and their silver complexes: Synthesis and antibacterial properties

Cited by 64 publications

References 45 publications

Silver–N‐Heterocyclic Carbene Complexes: Synthesis, Characterization, and Antimicrobial Properties

Silver–N‐Heterocyclic Carbene Complexes: Synthesis, Characterization, and Antimicrobial Properties

Bis-imidazolium and benzimidazolium based gemini-type ionic liquids structure: synthesis and antibacterial evaluation

Synthesis and In Vitro Anticancer Evaluation of Some Benzimidazolium Salts

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