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    Benzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and ?-glycosidase
    (Wiley, 2022) Tezcan, Burcu; Gok, Yetkin; Sevincek, Resul; Taslimi, Parham; Taskin-Tok, Tugba; Aktas, Aydin; Guzel, Bilgehan
    Here, we report the synthesis, characterization, and biological activities of a series of benzimidazolium salts bearing the trifluoromethylbenzyl group. All benzimidazolium salts were characterized by using nuclear magnetic resonance (NMR) (H-1 NMR and C-13 NMR), Fourier transform-infrared spectroscopy, and elemental analysis techniques. The crystal structures of some of these compounds were obtained by the single-crystal X-ray diffraction method. Furthermore, the acetylcholinesterase (AChE) and alpha-glycosidase (alpha-Gly) enzyme inhibition activities of these compounds were investigated. The obtained results revealed that 2e, with K-i value of 1.36 +/- 0.34 mu M against AChE and 3d with K-i value of 91.37 +/- 10.38 mu M against alpha-Gly, were the most potent compounds against both assigned enzymes. It should be noted that most of the synthesized compounds were more potent than standard inhibitor tacrine (TAC) against AChE. In silico studies, we focused on compound 2e, 3d, 3e, and 3f as potent inhibitors of AChE and alpha-Gly, the compound 2e showed good binding energy (-10.23 kcal/mol), among the three selected compounds and positive control (-10.18, -10.08, and -7.37 kcal/mol for 3d, 3f, and TAC, respectively). Likewise, as a result of the same compounds against the alpha-Gly enzyme, the compound 3d had the highest binding affinity (-8.39 kcal/mol) between the four selected compounds and the positive control (-8.27, -8.10, -8.06, and -7.53 kcal/mol for 3f, 3e, 2e, and acarbose, respectively). From the absorption, distribution, metabolism, excretion, and toxicity analyses, it can be concluded that the compounds under consideration exhibited more drug-likeness properties in the prediction studies compared to positive controls.
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    Benzimidazolium Salts Containing Trifluoromethoxybenzyl: Synthesis, Characterization, Crystal Structure, Molecular Docking Studies and Enzymes Inhibitory Properties
    (Wiley-V C H Verlag Gmbh, 2022) Hamide, Mahmut; Gok, Yetkin; Demir, Yeliz; Sevincek, Resul; Taskin-Tok, Tugba; Tezcan, Burcu; Aktas, Aydin
    The method for producing 4-trifluoromethoxybenzyl substituted benzimidazolium salts is described in this article. The method is based on the reaction of 4-trifluoromethoxybenzyl substituent alkylating agent with 1-alkylbenzimidazole. This method yielded 1-(4-trifluoromethoxybenzyl)-3-alkylbenzimidazolium bromide salts. These benzimidazolium salts were characterized by using H-1-NMR, C-13-NMR, FT-IR spectroscopy, and elemental analysis techniques. The crystal structure of 1f was enlightened by single crystal X-ray diffraction studies. Also, the enzyme inhibition effects of the synthesised compounds were investigated. They demonstrated highly potent inhibition effect on acetylcholinesterase (AChE) and carbonic anhydrases (hCAs) (K-i values are in the range of 7.24 +/- 0.99 to 39.12 +/- 5.66 nM, 5.57 +/- 0.96 to 43.07 +/- 11.76 nM, and 4.38 +/- 0.43 to 18.68 +/- 3.60 nM for AChE, hCA I, and hCA II, respectively). In molecular docking study, the interactions of active compounds showing activity against AChE and hCAs enzymes were examined. The most active compound 1f has -10.90 kcal/mol binding energy value against AChE enzyme, and the potential structure compound 1e, which has activity against hCA I and hCA II enzymes, was -7.51 and -8.93 kcal/mol, respectively.
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    Pentafluorobenzyl-substituted benzimidazolium salts: Synthesis, characterization, crystal structures, computational studies and inhibitory properties of some metabolic enzymes
    (Elsevier, 2022) Hamide, Mahmut; Gok, Yetkin; Demir, Yeliz; Yakali, Gul; Tok, Tugba Taskin; Aktas, Aydin; Sevincek, Resul
    This work contains the synthesis and characterization of the pentafluorobenzyl-substituted benzimidazolium salts which N -heterocyclic carbene (NHC) precursors. All compounds were characterized by using 1 H, 13 C, and 19 F NMR, FT-IR spectroscopy, and elemental analysis techniques. All the spectroscopy and elemental analysis data fully confirm the proposed formulas. In the synthesized compounds, the molecular structures of compounds 1-(2-methylbenzyl)-3-(2,3,4,5,6-pentafluorobenzyl)benzimidazolium bromide ( 1b ), 1-(4-methylbenzyl)-3-(2,3,4,5,6-pentafluorobenzyl)benzimidazolium bromide ( 1d ) and 1-(4-trifluoromethylbenzyl)-3-(2,3,4,5,6-pentafluorobenzyl)benzimidazolium bromide ( 1f ) were enlightened by single crystal X-ray diffraction studies. After enzyme inhibition study, a new series of pentafluorobenzyl-substituted NHC precursors were determined to be highly potent inhibitors for acetylcholinesterase (AChE) enzyme and carbonic anhydrases (hCAs) isoenzymes. K i values were found in the range of 7.20 +/- 1.31 to 28.26 +/- 5.72 nM for AChE , 10.25 +/- 0.93 to 40.93 +/- 3.89 nM toward hCA I as pervasive metal containing enzymes present in prokaryotes and eukaryotes, and 3.33 +/- 0.15 to 58.22 +/- 6.99 nM for hCA II as the key enzyme promising strategy for the treatment of neurological disorders such as Alzheimer's disease. The molecular docking study performed for compounds had higher potential inhibitory properties involved in a novel series of pentafluorobenzyl-substituted NHC precursors based on the binding energy and interaction types against AChE and hCAs. (c) 2022 Elsevier B.V. All rights reserved.
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    Synthesis, in vitro anticancer activities, and quantum chemical investigations on 1,3-bis-(2-methyl-2-propenyl)benzimidazolium chloride and its Ag(I) complex
    (Sage Publications Ltd, 2021) Serdaroglu, Goncagul; Sahin-Bolukbasi, Serap; Barut-Celepci, Duygu; Sevincek, Resul; Sahin, Neslihan; Gurbuz, Nevin; Ozdemir, Ismail
    1,3-Bis-(2-methyl-2-propenyl)benzimidazolium chloride and its Ag(I) complex are synthesized and the structures are elucidated using spectroscopies techniques. The molecular and crystal structures of the benzimidazolium salt are confirmed by X-ray crystallography. The molecular geometries of the benzimidazolium and its Ag(I) salt are analyzed using the B3LYP functional with the 6-311+G(d,p)/LANL2DZ basis set. The observed Fourier transform infrared and nuclear magnetic resonance isotropic shifts are compared with the calculated values. Besides, the quantum chemical identifiers, significant intramolecular interactions, and molecular electrostatic potential plots are used to show the tendency/site of the chemical reactivity behavior. The three-dimensional Hirshfeld surfaces and the associated two-dimensional fingerprint plots are applied to obtain an insight into the behavior of the interactions in the crystal. Both compounds are tested for their in vitro anticancer activities against DU-145 and MCF-7 cancer cells and L-929 non-cancer cells using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay.