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    Benzimidazolium Salts Bearing 2-methyl-1,4benzodioxane Group: Synthesis, Characterization, Computational Studies, In vitro Antioxidant and Antimicrobial Activity
    (Biointerface Research Applied Chemistry, 2021) Albayrak, Sevil; Gok, Yetkin; Sari, Yakup; Tok, Tugba Taskin; Aktas, Aydin
    This study contains the synthesis of the 1-(2-methyl-1,4-benzodioxane)benzimidazole and 2-methyl-1,4-benzodioxane substituted benzimidazolium salts. The benzimidazolium salts were synthesized from the reaction of the 1-(2-methyl-1,4-benzodioxane)benzimidazole and various aryl chlorides. All compounds were characterized using H-1 NMR, C-13 NMR, FTIR spectroscopy, and elemental analysis techniques. The antioxidant properties of benzimidazolium salts were examined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging and hydrogen peroxide scavenging ability assays. The compounds showed a moderate inhibitory effect on DPPH radical (The percent inhibition = 29.53-39.75). Also, the compounds exhibited significant H2O2 radical scavenging activity. Antimicrobial activities of the compounds were examined against nine bacterial strains and Candida albicans. All compounds displayed marked antimicrobial activity against tested microorganisms, particularly against Pseudomonas aeruginosa, Listeria monocytogenes, and C. albicans. From the computational perspective, benzimidazolium salts were also optimized at B3LYP / DMol3// DFT level using the Discovery Studio 2020 program. HOMO-LUMO analysis and molecular electrostatic potential surface (MESP) were exerted to examine the effects of benzimidazolium salts' electronic and structural properties.
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    BIOLOGICAL ACTIVITY EVALUATION OF NOVEL N-HETEROCYCLIC CARBENE PRECURSORS
    (Int Journal Pharmaceutical Sciences & Research, 2017) Akkoc, Senem; Gok, Yetkin; Erdogan, Hulya; Albayrak, Sevil
    Five novel benzimidazolium salts were synthesized as N-heterocyclic carbene (NHC) precursors (1a-e). They were characterized by different techniques. The antimicrobial activities of these compounds were tested. The compounds showed moderate activity against three Gram (+) and seven Gram (-) bacteria in comparison to tetracycline, which was used as the standard antibiotic, whereas all the compounds (1a-e) showed no activity against the test yeast C. albicans.
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    In vitro antimicrobial studies of new benzimidazolium salts and silver N-heterocyclic carbene complexes
    (Taylor & Francis Ltd, 2016) Gok, Yetkin; Akkoc, Senem; Erdogan, Hulya; Albayrak, Sevil
    A series of new benzimidazolium salts (1a-g) were synthesized from the reaction of 1-(4-vinylbenzyl) benzimidazole with various alkyl halides. These salts were used to synthesize silver N-heterocyclic carbene (Ag-NHC) complexes (2a-f). The thirteen compounds were characterized by FT-IR, NMR (H-1 and C-13) spectroscopic methods and an elemental analysis technique. These selected candidates were tested for their in vitro antimicrobial activities. Antibacterial and antifungal results indicated that the new salts, and particularly their silver complexes, were found to be strongly effective against seven Gram (-) bacterial strains, three Gram (+) bacterial strains and one yeast (Candida albicans).
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    N- Phenyl- substituted carbene precursors and their silver complexes: synthesis, characterization and antimicrobial activities
    (Wiley, 2014) Gok, Yetkin; Akkoc, Senem; Albayrak, Sevil; Akkurt, Mehmet; Tahir, Muhammad Nawaz
    A series of unsymmetrically substituted N-heterocyclic carbene (NHC) precursors (1a, 1b, 1c, 1d, 1e) were synthesized from the reaction of N-phenylbenzimidazole with various alkyl halides. These compounds were used to synthesize NHC-silver(I) complexes (2a, 2b, 2c, 2d, 2e). The five new 1-phenyl-3-alkylbenzimidazolium salts (1a, 1b, 1c, 1d, 1e) and their NHC-silver complexes (2a, 2b, 2c, 2d, 2e) were characterized by the H-1 NMR, C-13 NMR and FT-IR spectroscopic methods and elemental analysis techniques. Also, the two NHC-silver complexes 2b and 2c were characterized by single-crystal X-ray crystallography, which confirmed the linear C?Ag?Cl arrangements. The antibacterial activities of the NHC precursor and NHC-silver complexes were tested against three Gram-positive bacterial strains (Bacillus subtilis, Listeria monocytogenes and Staphylococcus aureus) and three Gram-negative bacterial strains (Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa) using the microdilution broth method. The NHC-silver complexes showed higher antibacterial activity than the NHC precursors. In addition, silver complexes 2a, 2b, 2c, 2d showed high antibacterial activity against the Gram-positive bacteria L. monocytogenes and S. aureus compared to the standard, tetracycline. Copyright (c) 2014 John Wiley & Sons, Ltd.