This study investigates the corrosion inhibition performance of a novel benzimidazolium bromide derivative containing a bromide counterion and a trifluoromethyl (CF3) substituent, namely 1-benzyl-3-(2-(trifluoromethyl)benzyl)benzimidazolium bromide (BF2), for mild steel (MS) corrosion in 1.0 M HCl using electrochemical techniques, surface analyses, and theoretical calculations. According to potentiodynamic (PD) polarisation analysis, in the presence of BF2, current densities of both cathodic and anodic regions are suppressed via strong adsorbing functional groups, suggesting the corrosion rate (CR) dramatically decreases from 21.645 mm year-1 to 0.659 mm year-1. The inhibition efficiency (eta) is increased from 97.5% to 98.8% with elevating BF2 concentration 0.5 mM to 10 mM by electrochemical impedance spectroscopy (EIS). The E a values are calculated as 52.64 kJ mol-1 and 97.50 kJ mol-1 for the MS in a blank and BF2-containing corrosive environment, respectively, suggesting a physical adsorption mechanism of BF2 onto the MS surface. Adsorption free energy ( Delta Gadso ) of the inhibitor is -38.35 kJ mol-1. The charge accumulation quantity (Q) is decreased from 259.70 to 11.36 C in an acidic environment with 10.0 mM BF2 at an overpotential of -0.25 V. Moreover, the outcomes of surface examination and quantum chemical calculation are consistent with electrochemical and surface analyses results. Cette & eacute;tude examine les performances d'inhibition de la corrosion d'un nouveau d & eacute;riv & eacute; de bromure de benzimidazolium contenant un contre-ion bromure et un substituant trifluorom & eacute;thyle (CF3), soit le bromure 1-benzyl-3-(2-(trifluorom & eacute;thyl)benzyl)benzimidazolium (BF2), pour l'acier doux (MS) dans du HCl 1.0 M, en utilisant des techniques & eacute;lectrochimiques, des analyses de surface et des calculs th & eacute;oriques. Selon l'analyse de polarisation potentiodynamique (PD), en pr & eacute;sence de BF2, les densit & eacute;s de courant des r & eacute;gions cathodiques et anodiques sont r & eacute;duites gr & acirc;ce & agrave; de forts groupes fonctionnels adsorbants, sugg & eacute;rant que la vitesse de corrosion (CR) diminue dramatiquement, passant de 21.645 mm an-1 & agrave; 0.659 mm an-1. L'efficacit & eacute; d'inhibition (eta) augmente de 97.5% & agrave; 98.8% lorsque la concentration de BF2 passe de 0.5 mM & agrave; 10 mM, comme le montre la spectroscopie d'imp & eacute;dance & eacute;lectrochimique (EIS). On a calcul & eacute; les valeurs d'& eacute;nergie d'activation (E a) & agrave; 52.64 kJ mol-1 et 97.50 kJ mol-1 pour le MS dans un environnement t & eacute;moin et dans un environnement corrosif contenant du BF2, respectivement, sugg & eacute;rant un m & eacute;canisme d'adsorption physique du BF2 sur la surface du MS. L'& eacute;nergie libre d'adsorption ( Delta Gadso ) de l'inhibiteur est de -38.35 kJ mol-1. La quantit & eacute; de charge accumul & eacute;e (Q) diminue de 259.70 & agrave; 11.36 C en milieu acide avec 10.0 mM de BF2 & agrave; une surtension de -0.25 V. De plus, les r & eacute;sultats de l'examen de surface et des calculs de chimie quantique sont conformes aux r & eacute;sultats des analyses & eacute;lectrochimiques et de surface.

This study presents the synthesis of acetyl-and fluorinated group-containing imidazol-2-ylidene silver complexes. The structures of the complexes obtained via deprotonation method were elucidated using spectroscopic techniques such as NMR, FTIR, and MS, as well as elemental analysis. In addition, the enzyme inhibition profiles of the synthesized Ag(I)-NHC complexes were thoroughly investigated against human carbonic anhydrase isoforms I and II (hCAs I and II), as well as acetylcholinesterase (AChE). Notably, compound 2f, bearing 2-chloro and 4-fluoro groups, exhibited superior inhibition potency against hCA I and AChE enzymes, with Ki values outperforming the reference inhibitors acetazolamide (AZA) and tacrine (TAC). These findings suggest that the dual halogenation pattern enhances both electrostatic and hydrophobic interactions within enzyme active sites. In addition, the cytotoxic activity of compound 2f was determined using MTT assays in SH-SY5Y (neuroblastoma), HCT-116 (colorectal carcinoma), and MCF-7 (breast adenocarcinoma) cell lines, yielding IC50 values of 35.63 +/- 0.84 mu M, 49.37 +/- 0.97 mu M, and 54.92 +/- 1.94 mu M, respectively. Further, we examined the inhibition potential of three most potent compounds (2a, 2e and 2f) with in silico molecular docking with three target proteins (hCA I, hCA II, and AChE). The binding energy score and ligand-protein interactions were indicating excellent inhibition potential of examined compounds. Overall, these results highlight the multi-target enzyme-blocking ability of 2f as a promising candidate for suppressing tumor growth.

A series of morpholine(Morp.)-liganded palladium(II) complexes (1a-c) and triphenylphosphine(PPh3)-liganded palladium(II) complexes (2a-c) bearing 4-fluorobenzyl substituted N-heterocyclic carbene (NHC) were synthesized from NHC-Pd(II)-pyridine and Morp./PPh3 by ligand exchange method. The new complexes were fully characterized using 1H NMR, 13C NMR, 19F NMR, 31P NMR, FTIR spectroscopy and elemental analysis techniques. Furthermore, single crystal X-ray diffraction was used to elucidate the structures of complexes 1a and 2b. The anticancer activities of the new complexes against MCF-7 (Human Breast Cancer) cell line were investigated. With an IC50 value of 37.54 for complex 1a, it can be said that it is more cytotoxic to MCF-7 cells compared to other complexes, while the least cytotoxicity was observed in complex 1b.

Cancer remains one of the leading causes of death worldwide, making the search for effective anticancer agents a critical area of research. In recent years, ruthenium-based compounds have gained significant attention due to their potential as novel candidates for cancer treatment. This report aims to explore the synthesis and anticancer properties of the Ru(II)oxothiazolidine complexes. All complexes have been prepared from ligands containing hydrazinyl-oxothiazolidine moiety and [RuCl2(p-cymene)]2 substrate. The basic skeleton of the complexes is justified with 1H-, 13C-NMR, and FTIR spectroscopic methods. The proposed structures of the complexes were further confirmed with elemental analysis. The crystal structure of the complex 2a has been determined by using single-crystal X-ray diffraction. Asymmetric unit of structure contains two crystallographically independent molecules, dichloromethane and two chloride anions. All complexes exhibited strong activity against MCF-7 (breast cancer) and HCT-116 (colon cancer) cancer cell lines better than standard anticancer drug cisplatin. The complex 2a showed the highest anticancer efficacy against MCF-7 (IC50: 13.89 mu M) and HCT-116 (IC50: 14.02 mu M). DNA binding study also demonstrates that all complexes have an interaction ability to DNA. Ethidium bromide fluorescence quenching assay revealed moderate DNA binding for complex 2a suggesting partial intercalation or groove binding with ct-DNA. Meanwhile, molecular docking simulations of potent rutheniumbased oxothiazolidine complexes (1a, 1c, and 2a) against breast (MCF-7) and (1a, 1c, and 2a) colon (HCT116) cancer cell models were carried out. The findings suggest that complex 2a is the best candidate complex for both cancers. Furthermore, complexes 1a and 1c demonstrated potent cytotoxic activity against MCF-7 breast cancer cells, whereas complexes 1b and 2d exhibited significant cytotoxic effects against HCT-116 colon cancer cells.

Seven new PEPPSI (Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation) type complex compounds containing bisbenzimidazole ligands were synthesized, and their structures were characterized by spectroscopic methods (1H, 13C-NMR, IR, HRMS). The catalytic activities of PEPPSI-precatalysts were tested in Suzuki-Miyaura cross-coupling reactions using phenylboronic acid, aryl bromides and aryl chlorides. It was observed that the precatalysts, having electron-dense benzimidazole ligands (compounds 1, 2), exhibited higher catalytic activity. In contrast, catalyst precursors having electron-poor benzimidazole ligands were found to have lower catalytic activity (compound 7).

Acetylphenyl and various fluorinated alkyl-functionalized imidazol-2-ylidene carbene complexes of Pd(II) were prepared by the reaction of dibromo[1-(4-acetylphenyl)-3-(fluorinatedalkyl)imidazole-2-ylidene]pyridinepalladium(II) with morpholine in dichloromethane. The structures of the synthesized complexes were characterized using spectroscopic such as 1H, 13C, 19F NMR, and FT-IR and elemental analysis techniques. The Pd(II) complex 2d, incorporating an N-heterocyclic carbene (NHC) and morpholine ligand, was structurally characterized by Xray crystallography. The crystal packing reveals N-H & ctdot;Br hydrogen bonds, C-H & ctdot;F/O interactions, and C-F & ctdot;it stacking, forming a 3D network stabilized by supramolecular interactions. The cytotoxicity of the synthesized compounds (2a-f) was evaluated using the MCF-7 cell line. The anticancer activity of palladium complexes against MCF-7 cells was revealed with IC50 values ranging from 48.13-151.02 mu M. The effect of complex 2b on the gene expression of the hERG1 K+ channel was determined using the RT-qPCR method. hERG1 potassium channel gene expression decreased at the 50 mu M complex 2b concentration at 24 h.

This work reports the synthesis and characterization of a series of PEPPSI-type (NHC)PdBr2(Py) complexes bearing ester-functionalized N-heterocyclic carbene (NHC) ligands. The complexes were characterized using 1H and 13C NMR, FTIR spectroscopy, and X-ray crystallography. Single-crystal X-ray diffraction confirmed the square-planar geometry around the Pd(II) center. The synthesized complexes demonstrated significant inhibitory ability against alpha-glycosidase, acetylcholinesterase (AChE), and butyrylcholinesterase (BChE), with Ki values ranging from 17.63 +/- 2.65 to 106.13 +/- 3.78 nM. Molecular docking studies revealed key interactions between the complexes and the active sites of the target enzymes, providing insights into their inhibitory mechanisms. Notably, complexes 1f, 1i, and 1e exhibited the highest potency, suggesting their potential as therapeutic agents for metabolic and neurodegenerative disorders.

N-heterocyclic carbenes (NHCs) are chemical structures called heterocyclic structures that contain one or more nitrogen atoms. N-heterocyclic compounds are the basic building blocks of many drugs and biologically active molecules. One of these compounds is benzimidazolium salts. Herein, we present the synthesis of a series of phenylsulfonylethyl-substituted benzimidazolium salts. These compounds were characterized using NMR (1H- and 13C-) and FTIR spectroscopic techniques. Compound 1b exhibits a U-shaped benzimidazolium cation paired with a chloride anion. A hierarchical supramolecular architecture arises from C-H⋯Cl chains, C-H⋯π layers, and π⋯π stacking, demonstrating cooperative non-covalent stabilization of the crystal structure. The synthesized benzimidazolium derivatives exhibited notable inhibitory effect against human carbonic anhydrases (hCA I, hCA II)and acetylcholinesterase (AChE), with several compounds showing markedly lower Ki values than the clinical standards. Molecular docking of the NHCs with different receptors showed excellent binding capability with the active site of the target receptors. Moreover, the physicochemical and ADME analysis of the compounds were performed with SwissADME software. Overall examined compounds were found with very good oral bioavailability determined by Lipinski and Verber's rule. The compounds showed Pgp susceptibility with reasonable blood brain barrier permeability.

In this study, we report the synthesis and anticancer activities of new ruthenium complexes with N-heterocyclic carbene (NHC) ligands, which are of great significance for drug delivery research. For this reason, 4-methylsulfonylbenzyl-substituted benzimidazole-functionalized Ru(II)NHC complexes were synthesized in our research. The characterization of these new complexes were performed using appropriate spectroscopic methods (1H NMR, 13C NMR, and FT-IR) and elemental analysis techniques. The crystal structure of complex 1c was obtained using single crystal X-ray diffraction. MTT method was used to understand in vitro anticancer activities of the complexes against MCF-7 (breast cancer), HCT-116 (colon cancer), SH-SY5Y (brain cancer), and HeLa (cervical cancer) cell lines. Based on the IC50 values determined by MTT assay, the most effective complex was identified as 1 h. DNA binding analyses were carried out using agarose gel electrophoresis, revealing that 1 h weakly interacted with DNA. Additionally, the effects of 1 h on cell cycle progression and apoptosis in the SH-SY5Y cell line were examined using flow cytometry. The results indicated that 1 h induced G0/G1 phase accumulation and increased apoptotic cell death. These findings suggest that the synthesized complex 1 h has a significant anticancer potential.

BACKGROUND:This work presents the synthesis of Ru(II)NHC complexes bearing a series of 4-fluorobenzyl group. These complexes have been characterized by a variety of spectroscopic methods (1H NMR, 13C NMR, and FTIR) and by elemental analysis techniques. METHODS:These complexes' antitumor activities against SH-SY5Y (human neuroblastoma) and HCT116 (human colon cancer) were investigated by 3-(4,5-dimethylthiazole-2-yl)-2,5-biphenyl tetrazolium bromide (MTT) assay. RESULTS:The results showed that all the synthesized complexes exhibited significant cytotoxic effect with low IC50 values 15 ± 0.57, 15.26 ± 0.71, 7.64 ± 0.30, 27.66 ± 0.36 and 14.45 ± 0.84 (μg/mL) respectively. CONCLUSION:Furthermore, apoptosis assessed by double labeling with Annexin V-FITC/PI indicated that complexes 1b and 1d can effectively induce apoptosis and inhibit cell proliferation at the S phase in SH-SY5Y cells. Taken together, Ru(II)NHC complexes containing the 4- fluorobenzyl group have significant potential for the development of novel, highly effective anticancer agents.

In this work, the synthesis of several unsymmetrical benzimidazolium salts with an ester (2-ethoxy-2-oxoethyl) group on the nitrogen atom is described. The structures of all compounds were fully characterized by spectroscopic (1H, 1 H, 13 C NMR, FTIR) and analytical (elemental analysis) methods. However, single-crystal X-ray diffraction analysis elucidated the molecular and crystal structures of compounds 1a and 1c . Asymmetric units of both crystal structures contain two crystallographically independent molecules and two bromide anions. All compounds exhibited substantial inhibition against the cytosolic carbonic anhydrase isoforms (hCA I and hCA II) and acetylcholinesterase (AChE) with Ki i values 51.00-45.18 nM, 46.94-305.65 nM, and 17.57-65.68 nM, respectively. Notably, compound 1d showed extreme inhibitory effect against hCA I with 51.00+5.31 +5.31 nM (AZA: 275.44+13.32 +13.32 nM), hCA II with 46.94+5.44 +5.44 nM (AZA: 236.55+17.88 +17.88 nM) and AChE with 17.57+3.14 +3.14 nM (TAC: 80.44+6.88 +6.88 nM). In silico approach showed that compound 1d could form stable complexes with target enzymes with a different binding affinity (BE:9.01 kcal/mol for AChE;-7.22 kcal/mol for hCA II and-6.51 kcal/mol for hCA I). The results supported the medical potential of benzimidazolium salts containing ester group. They significantly lighted our knowledge about the chemistry of side groups on phenyl ring especially in the para position as compared to ortho and meta positions.

Herein, the synthesis of silver(I)-N-heterocyclic carbene (Ag(I)NHC) complexes is presented. These complexes were synthesized from imidazolium salts and silver oxide via the deprotonation method. Ag(I)NHC complexes were characterized using various spectroscopic and analytical techniques, including FTIR, NMR, and elemental analysis. The single crystal structures of the complexes 1e and 1g were illuminated through x-ray crystallography. The study demonstrates that the geometrical characteristics of both complexes closely match those of previously described complexes with a comparable ligand structure. Acetylcholinesterase (AChE) inhibitors prevent the excessive breakdown of acetylcholine by acting on acetylcholinesterase in its neurotransmission. In this way, they help to improve cognitive functions in patients with AD. On the other hand, human carbonic anhydrase inhibitors (CAIs) have been used clinically for many years as antiepileptic, antiglaucoma, antimetastatic, antitumor, and diuretic agents. In this study, the enzyme inhibition abilities of seven imidazol-2-ylidene-silver(I) complexes bearing 4-acetylphenyl side arm were examined against AChE and hCAs. These molecules exhibited a highly potent inhibition effect on AChE and hCAs (Ki values are in the range of 16.27 +/- 1.81 to 130.79 +/- 11.98 nM for AChE, 13.22 +/- 1.88 to 182.14 +/- 33.93 nM for hCA I, and 12.72 +/- 1.99 to 62.36 +/- 9.21 nM for hCA II). Novel imidazol-2-ylidene-silver(I) complexes bearing 4-acetylphenyl side arms 1a-g displayed efficient inhibitory profiles for the examined metabolic enzymes. Docking was additionally performed to investigate the interactions of the current complexes 1a-g with hCA I, hCA II, and AChE proteins. It has been determined that compound 1d has activity against all the tested proteins, with the most effective interaction observed with hCA I. The pharmacokinetic properties of the three top potent complexes for each target against the related proteins were also examined using the SwissADME and pkCSM web tools. In the meantime, the stabilities of the complexes with the highest binding potential according to the docking study were assessed through molecular dynamics simulation. The AChE-1a complex was found to be the one with relatively high stability. Also, further energy computations were made by using the MD simulation results. The compounds have been estimated to bind strongly with their targets.

Herein, the synthesis of 1-alkyl-5(6)-benzoyl-substituted benzimidazoles and their 1,3-bisalkylbenzimidazolium halide salts are presented and evaluated for some metabolic enzyme inhibition. All compounds were characterized using various spectroscopic techniques. Single-crystal XRD analysis was performed to determine the molecular structure of two compounds. The newly synthesized compounds exhibited significant inhibitory effects against acetylcholinesterase (AChE) and human carbonic anhydrase isoforms I and II (hCA I and hCA II) enzymes. These compounds demonstrated promising inhibition profiles, with Ki values ranging from 12.4 ± 5.4 to 109.4 ± 49.9 nM for hCA I, 23.1 ± 11.2 to 115.0 ± 17.9 nM for hCA II, and 0.7 ± 0.3 to 4.4 ± 1.0 nM for AChE. In comparison, the reference compound acetazolamide showed Ki values of 30.5 ± 6.7 nM and 37.4 ± 7.8 nM against hCA I and hCA II isoenzymes, respectively. Additionally, tacrine, a known AChE inhibitor, exhibited a Ki value of 5.1 ± 2.7 nM. The dual inhibition of CA and AChE represents a valuable pharmacological approach with a wide range of therapeutic applications. The explanation and evaluation of the enzyme inhibition data obtained in line with the interactions of the synthesized compounds with hCA I, hCA II, and AChE enzymes were carried out by molecular docking studies. In particular, we focused on the three compounds (4e, 4f, and 4j for hCA I; 3g, 4f, and 4k for hCA II; and 4e, 4f, 4j, and 4l for AChE) with the highest potential activity with each enzyme. The physicochemical, ADME, drug-likeness, medicinal chemistry, and toxicity properties of the potential ligands were then predicted so that their drug candidate suitability for further studies is revealed.

This study investigates and compares the corrosion inhibition performance of two benzimidazolium salts (BIS1 and BIS2), previously synthesized by Albayrak et al. and Sar & imath; et al., respectively. These inhibitors were tested in a 1 M hydrochloric acid solution on mild steel. The two compounds differ in their substituents: BIS1 features an electron-donating group, whereas BIS2 contains an electron-accepting substituent. Electrochemical methods, including potentiodynamic polarization (PDP), electrochemical impedance spectroscopy (EIS), and weight-loss measurements, consistently demonstrated superior inhibition efficiency for BIS1, exceeding 95 % at 10-3 M concentration. The performance disparity between BIS1 and BIS2 further increased with rising temperatures. Surface characterization by scanning electron microscopy (SEM), energy dispersive X-ray spectrometer (EDX), atomic force microscopy (AFM), and X-ray Photoelectron Spectroscopy revealed that BIS1 forms a denser and more adherent protective film on the steel surface. Molecular modeling techniques, including Density Functional Theory (DFT), Tight-binding DFT (DFTB), and Molecular Dynamics (MD) simulations, provided further insights, showing that the enhanced performance of BIS1 is primarily attributed to its higher HOMO energy, facilitating stronger chemisorption via electron donation to the metal surface. These findings challenge the conventional understanding of purely electrostatic adsorption for cationic inhibitors and underscore the significant potential of substituted benzimidazolium salts as efficient corrosion inhibitors.

This study presents the synthesis of new Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation (PEPPSI) type N-heterocyclic carbene (NHC)-Pd(II) complexes featuring a 4-acetylphenyl side arm, which demonstrate stability in the presence of air and moisture and function as homogeneous catalysts. All complexes were characterized using the elemental analysis technique and FTIR, 1H NMR, and 13C NMR spectroscopic methods. In addition, the molecular and crystal structures of the five complexes (2a, 2c, 2d, 2e, 2g) were determined by single crystal X-ray diffraction (SC-XRD). These complexes have been investigated for their catalytic abilities in the Suzuki-Miyaura cross-coupling reactions of aryl chlorides and bromides with aryl boronic acid derivatives, the Heck cross-coupling reactions of aryl bromides with styrene, and the cross-coupling reactions of aryl bromides with phenylacetylene. In addition, we investigated the catalytic activities of some complexes (2e, 2g) in the Sonogashira coupling reaction. The catalytic activities of these homogeneous catalysts in C-C coupling reactions were determined by varying various parameters such as solvent, base, temperature and time. They were found to be active catalysts under these conditions.

Introduction:The discovery of alternative drugs has gained importance due to the many side effects of these drugs used for treatment. Methods:Herein, the synthesis of a series of unsymmetrical imidazolium salts containing 4-acetylphenyl/4-formylphenyl and bioactive heterocyclic groups such as morpholine, piperidine, pyrrole or pyridine was reported. 4-(1-H-imidazol-1-yl)acetophenone and 4-(1-H-imidazol-1-yl)benzaldehyde were used as salt precursors. Alkyl halides containing heterocyclic groups such as 2-morpholinoethyl hydrochloride, 2-pyrrolidinoethyl hydrochloride, 2-piperidinoethyl hydrochloride and pyridin-2-ylmethyl bromide hydrobromide were used. Thus, there are two positively charged nitrogens in the structure of these salts synthesized by the quaternization method. The structures of all salts were fully characterized by 1H, 13C NMR, FTIR spectroscopic and elemental analysis methods. the a series of imidazolium salts (1a-d and 2a-d) were designed, synthesized and fully characterized by spectroscopic methods. Results:The inhibitory effect against AChE of the series compounds was evaluated as in vitro and in silico studies. The results indicated that the compounds showed remarkably potent inhibitory effects on AChE with K I values ranging from 0.63 ± 0.04 μM to 11.23 ± 1.05 μM and IC50 values spanning from 0.82 ± 0.06 μM to 14.75 ± 0.82 μM. The antimicrobial activities of the synthesized compounds were measured by inhibition of bacterial growth expressed as minimum inhibitory concentration (MIC) values. It was observed that the synthesized compounds exhibited antimicrobial activity especially against Gram negative bacteria. In addition, the results of molecular docking studies of bacteria supported our antimicrobial results. Conclusions:The results suggested that the synthesized compounds showed the potential to be antimicrobial and acetylcholinesterase inhibitors.

In this paper, a new palladium -based (NHC)Pd(II)(Morp) complexes (NHC: N -heterocyclic carbene, Morp: morpholine) were prepared. The NHC ligand in these complexes bears the 2-chloro-4-fluorobenzyl group. All complexes were fully characterized by 1 H, 13 C NMR, FTIR spectroscopic and elemental analysis methods. The crystal structure of complex 1f has been determined by using single-crystal X-ray diffraction. Furthermore, all complexes were investigated for their ability to inhibit enzymes. All complexes exhibited highly potent inhibition effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes (K i values are in the range of 97.84 +/- 8.97 to 132.28 +/- 11.63 mu M and 18.24 +/- 2.08 to 39.08 +/- 5.28 mu M for AChE and BChE, respectively). Designing of reported complexes is impacted by molecular docking study, because with molecular docking study, it will lead to future researches by illuminating the interaction mechanism of complexes 1a , 1b , 1c and 1f with potential activity against target AChE and BChE enzymes at molecuar level.

Eight new bisbenzimidazolium halides were prepared from alkyl halides and 4,4′-bis[(benzimidazol-1-yl)methyl]-1,1′-biphenyl.The structures of the benzimidazole salts were characterized using elemental analysis techniques as well as 1H, 13C NMR, and FT-IR spectroscopic methods. The inhibitory effects of the benzimidazole derivatives were measured against human carbonic anhydrase I (hCA I), human carbonic anhydrase II (hCA II), and acetylcholinesterase (AChE) enzymes. All benzimidazolium halides exhibited significant enzyme inhibitory properties. They showed highly potent inhibitory effect on AChE and hCAs (Ki values are in the range of 15.7 ± 0.8 to 49.7 ± 10.1 nM, 14.6 ± 1.5 to 70.7 ± 2.7 nM, and 17.4 ± 2.8 to 38 ± 10 nM for AChE, hCA I, and hCA II, respectively). The binding orientation of the synthesized bisbenzimidazolium halides was evaluated by molecular docking studies, reflecting the importance of the p-methylbenzyl, m-methylbenzyl, p-nitrophenethyl, and 3-(1,3-dioxoisoindolin-2-yl)methyl) groups in protein–ligand interaction. The docking results support the Ki values of the respective compounds in this study. The structure–activity relationships against the various targets are clearly shown in three dimensions at the atomic level by their interactions with the mentioned enzymes.

Here, a number of symmetric and unsymmetric N-heterocyclic carbene (NHC) precursors based on benzimidazol-2-ylidene are synthesized. The N-benzyl substituent in these compounds has an electron-withdrawing group (F) at the para position. The structure of these compounds was characterized using elemental analysis and various spectroscopic methods (FTIR and NMR). The molecular and crystal structures of compound 1f and compound 1h were unambiguously elucidated through single-crystal X-ray diffraction analysis. According to the X-ray studies, compound 1f exhibits the formation of a U-shaped molecule whereas compound 1h has a Z-shape formation. In addition, the enzyme inhibition activities of these compounds were investigated against acetylcholinesterase (AChE) and carbonic anhydrases (hCAs). They showed a highly potent inhibition effect on AChE and hCAs (Ki values are in the range of 14.84 +/- 1.91 to 174.80 +/- 23.60 nM for AChE, 22.41 +/- 1.93 to 188.67 +/- 27.05 nM for hCA I and 35.29 +/- 7.21 to 136.55 +/- 17.61 nM for hCA II). These results may contribute to the design and development of new drug candidates, particularly for treatment of some widespread disorders displayed in the world including Alzheimer's disease and glaucoma.

Herein, a series of N-heterocyclic carbene (NHC) precursors bearing sulfonyl moieties was prepared. 1-(4-(methylsulfonyl)benzyl)-3-alkylbenzimidazolium chloride salts were synthesized with the reaction of 1-alkylbenzimidazoles with 4-(methylsulfonyl)benzyl chloride. These compounds were characterized by using 1 H NMR, 13 C NMR, FT-IR spectroscopy and elemental analysis techniques. Molecular and crystal structures of compounds 2e and 2j were determined by using the single-crystal X-ray diffraction method. Furthermore, enzyme inhibitory properties of benzimidazolium salt were tested against xanthine oxidase (XO) and acetylcholinesterase (AChE), then determined the IC50 value range of XO were determined from 0.218 to 1.927 mu M, while the IC50 for AChE were determined from 1.328 to 5.22. Docking applications were used by using AutoDock4 in order to define the binding pose of the selected compounds, ( 2c, 2d and 2g ) and also to visualize the correlation of the generated optimal complexes. It is found that the compound 2g has good binding affinity (-11.24 kcal/mol) against AChE, on the other side, compound 2c shows the lowest binding energy (-8.32 kcal/mol) for the XO target. These findings and the defined compounds could be as potential agents to develop effective medicine for AChE and XO in the future.(c) 2022 Elsevier B.V. All rights reserved.