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    Microwave-assisted synthesis of 1-substituted-1H-benzimidazolium salts: Non-competitive inhibition of human carbonic anhydrase I and II
    (Wiley-V C H Verlag Gmbh, 2019) Karlik, Ozgul; Gencer, Nahit; Karatas, Mert O.; Ergun, Adem; Cikrikci, Kubra; Arslan, Oktay; Alici, Bulent
    A series of 1-substituted-1H-benzimidazolium p-toluenesulfonate salts were synthesized in good yields by the reaction of 1-substituted benzimidazole derivatives and p-toluenesulfonic acid under microwave irradiation. Two iodide salts were synthesized by the anion exchange reaction of the corresponding p-toluenesulfonate salt and NaI. All compounds were characterized by H-1 NMR, C-13 NMR, IR, LC-MS spectroscopic methods, and elemental analyses. The crystal structure of 1-methoxyethyl-1H-benzimidazolium p-toluenesulfonate 2d showed that cation and anion are interconnected by N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds. All compounds were examined as inhibitor of human carbonic anhydrase (hCA) I and II, and all of them inhibited hCA I and hCA II. Kinetic investigation results revealed that these compounds inhibit hCA I and hCA II in a non-competitive manner. The iodide salts had higher inhibitory activity than their corresponding p-toluenesulfonate salts.
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    Synthesis, structural characterization and cytotoxicity studies of T-shaped silver(I) complexes derived from 1-benzyl-3H-benzimidazolium p-toluenesulfonates
    (Pergamon-Elsevier Science Ltd, 2018) Karlik, Ozgul; Balcioglu, Sevgi; Karatas, Mert Olgun; Ates, Burhan; Alici, Bulent; Ozdemir, Namik
    In the present study, we synthesized novel benzimidazole-silver(I) complexes (2a-d) by the interaction of 1-benzyl-3H-benzimidazolium p-toluenesulfonate derivatives (1a-d) and Ag2O in order to investigate their anticancer properties. All the salts and complexes were fully characterized by H-1 NMR, C-13 NMR, IR and LC-MS spectroscopic techniques, elemental analysis and single crystal X-ray crystallography. Cytotoxic effects of compounds were investigated by MTT test against human colorectal (Caco-2), breast (MCF-7) cancer cell lines and non cancer mouse fibroblast (L-929) cell lines. All the complexes performed more cytotoxicity than cisplatin against Caco-2 cell lines while they were not active against MCF-7 in the treatment concentrations. Among the complexes, 2d which contains chlorine at 2-position of benzyl was found out as most active but not selective for non cancer L-929 cell lines. The complex 2b which contains methyl instead of chlorine at 2d showed approximately equal cytotoxicity as cisplatin against L-929 cell lines while this complex was twofold active than cisplatin against Caco-2 cell lines. These findings suggest that complex 2b is a promising candidate for treatment of colorectal cancer. (C) 2018 Elsevier Ltd. All rights reserved.