Refernces
10.14233/ajchem.2015.17567
The research primarily focuses on the synthesis and structural characterization of four novel 2-(hydroxyethoxy substituted)phenyl benzimidazoles, which are derivatives of benzimidazole known for their various biological and physiological activities. The study employs two distinct synthetic routes to produce these compounds, starting from commercially purchased materials without further purification. Route I involves the reaction of hydroxyl substituted benzaldehyde with o-phenylendiamine to form intermediates, which are then subjected to an o-hydroxyethylation reaction with chlorohydrin to yield the final products. This route is applicable for compounds where the hydroxyethoxy group is in the para- or meta-position relative to the benzimidazole in the benzene ring. Route II, used for ortho-substituted phenyl benzimidazole due to steric hindrance, synthesizes hydroxyethoxy substituted benzaldehyde first, which then reacts with o-phenylendiamine. The synthesized compounds were characterized using various analytical techniques including melting point determination, infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and elemental analysis. Single-crystal X-ray diffraction analysis was also conducted to confirm the structures and provide insights into the stereochemistry of the molecules.
10.1016/j.cclet.2013.11.026
The research focuses on the synthesis of benzimidazole-bearing 2-pyridone derivatives as potential antimicrobial agents to combat multi-drug resistance in bacteria and fungi. The study employed molecular hybridization to combine the bioactive properties of 2-pyridones and benzimidazoles into a single molecular framework. The synthesis involved the preparation of intermediate compounds through reactions with cyanoacetic acid hydrazide and Knoevenagel products, followed by condensation with aromatic aldehydes in boiling ethanol. The synthesized compounds were characterized using elemental analysis, infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry. The antimicrobial activity of the compounds was evaluated in vitro using the broth dilution method against various bacterial and fungal strains, with chloramphenicol and ketoconazole as standard drugs. The study also assessed the cytotoxic effects of the most potent compounds on human cancer cell lines. The findings indicated that compounds with electron-withdrawing groups, particularly at the meta or para position of the phenyl ring, exhibited the highest antibacterial activity, while a chlorine-substituted compound showed the most potent antifungal activity, with none of the tested compounds showing significant cytotoxic effects.
10.2174/138620712800194521
The research focuses on the development of a rapid and efficient one-pot synthesis method for benzimidazoles, which are important heterocyclic compounds with a wide range of biological activities and applications in pharmaceuticals. The method incorporates light fluorous-tag technology, enabling easy diversification and purification of benzimidazoles through fluorous solid-phase extraction (F-SPE). The key transformation involves the in situ reduction of aromatic nitro compounds, amide formation, cyclization, and aromatization, all facilitated by microwave irradiation. The study explores the substrate scope and reaction efficiency, finding that the reaction temperature is highly dependent on the nature of the carboxylic acids used. Various analytical techniques, including TLC, NMR, MS, and HPLC, were employed to monitor the reactions and characterize the intermediates and final products. The experiments resulted in the successful synthesis of a library of benzimidazoles with excellent yields, demonstrating the potential of this method for high-throughput screening and drug discovery.
10.1002/chem.201303341
The study investigates the DMSO-mediated ligand dissociation in N-heterocyclic-[Ru(h6-arene)Cl2] drug candidates, which are ruthenium-based organometallic complexes with potential anticancer and antiparasitic activities. The research focuses on the "piano-stool" complexes, so named due to their structural composition, and their tendency to dissociate when dissolved in dimethyl sulfoxide (DMSO), a common solvent used for preparing stock solutions in biological assays. The study used various ruthenium complexes with different N-heterocyclic ligands, such as benzimidazoles, imidazoles, pyridine, and quinoline derivatives, to understand the extent of ligand dissociation and its impact on the complexes' biological activity. The purpose of the study was to determine if the biological activity reported for these complexes could be influenced by the ligand dissociation occurring in DMSO, which could lead to a reconsideration of previous conclusions and potentially impact the development of new metal-based drugs. The study also explored the possibility of a "mix-and-screen" approach, where mixing [Ru(h6-arene)Cl2(DMSO)] complex with biologically active N-heterocyclic ligands could enhance the activity of certain potent ligands, offering a new strategy in drug discovery.
10.1007/s10593-008-0093-6
The study focused on the reaction of phenyl glycidyl ether with various heterocyclic compounds to synthesize new compounds with potential biological activity. The chemicals used included 5,5-dimethylhydantoin, morpholine, benzotriazole, benzimidazole, pyrrolidone, phthalimide, and 8-hydroxyquinoline. These heterocyclic compounds served as reactants to form N-(2-hydroxy-3-phenoxypropyl) derivatives, which are of interest due to their potential to contain pharmacophoric fragments that could lead to the discovery of new biologically active substances. The purpose of the study was to develop a one-stage method for synthesizing these derivatives, which could be applied in preparative chemistry and contribute to the development of new drugs.
10.1002/chem.201502487
The study presents a bioinspired catalytic aerobic oxidative C-H functionalization of primary aliphatic amines, leading to the synthesis of 1,2-disubstituted benzimidazoles, which are significant in drug discovery. The process employs a biomimetic cooperative catalytic system that includes a copper(II) salt (CuBr2) as an electron transfer mediator and an o-iminoquinone organocatalyst (1ox) derived from o-aminophenol (1red), to activate the α-C-H bond of primary amines under ambient air. This atom-economical multistep reaction proceeds under mild conditions and is environmentally friendly, offering a convenient strategy for functionalizing non-activated aliphatic amines. The study also explores the reactions of various primary amine substrates with o-aminoanilines, resulting in the formation of benzimidazoles with different substituents. The synthesized benzimidazoles are important as they are found in pharmaceutical products such as antihypertensives and antihistaminic agents.
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