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Abstract A new N-heterocyclic carbene (NHC) salt was synthesized by the reaction of 1-allyl benzimidazole with 2-methyl benzyl chloride. The structure of N-heterocyclic carbene salt was determined by elemental analysis, FT-IR, 1 H NMR and 13 C NMR spectroscopy and supported by the computational spectral analyses. For this purpose, the stable conformational structures obtained by Potential Energy Surface (PES) scan at B3LYP/6-31G (d,p) level of the theory have been used to elucidate the spectroscopic studies of the NHC salt as well as to search the electronic properties being important to predict the chemical reactivity behavior and nonlinearity properties of the NHC salt. FMO amplitudes and MEP diagrams have been used to show the chemically active sites of each stable conformer. Graphical abstract Image 1 Highlights • Synthesis and characterization of the NHC salt. • The structure was investigated by NM and FT-IR spectroscopy. • Stable conformers of NHC salt were revealed by computational modeling. • Spectral data were compared with computational ones. • NBO, NLO, FMO and MEP diagrams were investigated by computational tools. [ABSTRACT FROM AUTHOR]

• Benzimidazolium salts bearing 4-(methylthio)benzyl group were synthesized. • All compounds were characterized by NMR and FTIR spectroscopic techniques. • One compound was examined by the single-crystal X-ray diffraction method. • Inhibitory effects of all compounds were been tested against XO and AChE enzymes. • Molecular docking work was conducted on the chosen compounds against AChE and XO. The sulfurous compounds are known as organosulfur, which has been associated with numerous biological activities in both natural products and synthetic organic compounds. In this work, we present the synthesis of a series of 4-(methylthio)benzyl substituted benzimidazolium salts. All compounds were characterized using NMR (1H and 13C) and FTIR spectroscopic methods as well as an elemental analysis technique. The molecular and crystal structures of the compound 1a were determined by X-ray crystallography revealing that the compound crystallized in the trigonal space group R-3. Enzyme inhibition studies demonstrated that a new series of sulfurous compounds precursors were highly potent inhibitors for xanthine oxidase (XO) and acetylcholinesterase (AChE) enzyme. The IC 50 values were found in the range of 0.548 ± 0.033 to 0.725 ± 0.043 µM for XO promising strategy for the treatment from gout disease, while IC 50 values were found in the range 0.813 ± 0.076 to 1.149 ± 0.072 µM toward AChE as the key enzyme promising strategy for the treatment of neurological disorders such as Alzheimer's disease (AD). Furthermore, pharmacodynamics studies prove the binding interaction patterns, structural orientations and drug potential of sulfide derivatives in the binding sites of xanthine oxidase (XO) and acetylcholinesterase (AChE) enzymes. Potential inhibitors (compounds 1d-f) were compared with standard compounds allopurinol (for XO) and donepezil (for AChE). Compared to the positive compound of target XO, the 4-vinylbenzyl group of potential compound 1f and the 4-methylbenzyl group of compound le more effectively formed electrostatic and hydrophobic interactions with the target's interaction site. While donepezil as standard compound interacts only at the peripheral anionic site of AChE, the related compounds interact with both regions (PAS and CAS sites) of the same target. These compounds were placed at the active sites of the respective targets by molecular docking method using AutoDock software. Binding energy, binding modes and interaction types were used to evaluate the series of 4-(methylthio)benzyl substituted benzimidazolium salts's ability to bind to each target. Binding energy lower than zero remarks spontaneous binding, and equal and/or lower than -5 kcal/mol remarks good binding. Besides XO, the related compounds show higher activity against the AChE enzyme. They can also be analyzed as strong candidate compounds in biological studies of related enzymes. [ABSTRACT FROM AUTHOR]

• Novel silyl-tethered benzimidazolium salts were synthesized via stepwise N-alkylation of benzimidazole. • These salts were characterized by elemental analysis, IR, 1H, 13C NMR spectroscopy. • Their antibacterial and antifungal activities were investigated. • These salts showed good antimicrobial activity. A series of new silyl-substituted benzimidazolium salts were synthesized in good yield by the reaction of 1-(dimethylvinylsilyl)methylbenzimidazole and various alkyl halides. These salts were characterized by spectroscopic techniques. Also, crystal structure of 2c has been determined by the single-crystal X-ray diffraction method. Newly synthesized compounds were tested for antibacterial and antifungal activities and the minimum inhibitory concentrations were determined. The results indicates that some of compounds exert effective antibacterial activity against four Gram (-) bacterial and four Gram (+) bacterial strains and two yeast strains. [Display omitted] [ABSTRACT FROM AUTHOR]

• The benzimidazolium salt has been prepared from the benzimidazole and alkyl halide. • The benzimidazolium salt was characterized by NMR and FTIR spectroscopic techniques. • The structure of benzimidazolium salt was elucidated by the XRD method. • The cytotoxic activities of the Ag(I)-NHC complexes have been examined against two human cancer cell lines (MCF-7, MDA-MB-231), non-tumorigenic cell MCF 10A. • The biological activities of Ag(I)-NHC complexes differed depending on the nature of the NHC ligands. The main problems encountered in treatment with anticancer drugs, undesired side effects, and toxicity. One of the most important parameters in cell transport is the lipophilic and solubility property of the drug. Enough with the potential effects, side effects with minimal demand for new anticancer compounds, mechanisms of action of the compound can meet because of increased efforts to be clarified. In this case, scientists were encouraged to do new research. In particular, the organometallic compounds are one of the topics focused lately. Ag(I)-NHC complexes are one of the most important classes of organometallic compounds. Although the anticancer activity of Ag(I)-NHC complexes have been known recently times, the anticancer effects of 2-morpholino ethyl substituted benzimidazolium derivative, lipophilic, and solubility properties. Ag(I)-NHC complexes have not unknown yet. Therefore, we aimed to investigate of cytotoxic effect and apoptosis mechanism on breast cancer cell lines (MCF7), breast adenocarcinoma cell lines (MDA-MB-231), and non-tumorigenic epithelium cell lines (MCF 10A) of new Ag(I)-NHC complexes that derivative from morpholine-linked benzimidazole, were synthesized and antimicrobial activity was determined in our previous study. The cytotoxicity was determined by the MTS method, and the apoptosis mechanisms were determined the cell cycle, Annexin V, and caspase-3 analysis. A new benzimidazolium salt bearing morpholino ethyl substituent (2) was synthesized. This benzimidazolium salt was characterized by NMR and FT-IR spectroscopic method and elemental analysis technique. Also, the structure of the new benzimidazolium salt was confirmed by single-crystal X-ray diffraction. Ag(I)-NHC complexes inhibited the growth of MCF7 and MDA-MB-231 cells depending on the dosage and time. The complexes 3a and 3b exhibited a significant difference p < 0.05; p < 0.001; and p < 0.001 level depend on depending on the increase in concentration on cancer cells. All compound induced by apoptosis was associated with stopping the cell cycle in phase G1 and the caspase-3 activity exhibited. The complex 3c was the lowest number of caspase-activating cells (2.1%) compared with both the control and other complexes in MDA-MB-231 cells. But the complex 3a was the highest number of caspase-activating cells (% 9.6). These findings have shown that these new Ag(I)-NHC complexes can be important new anticancer agents for breast cancer treatments. Image, graphical abstract [ABSTRACT FROM AUTHOR]