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Upstream product

• 100-70-9 2-Cyanopyridine 
• 108-44-1 1-amino-3-methylbenzene 
• 98-98-6 2-Picolinic acid 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 1121-60-4 pyridine-2-carbaldehyde 
• 89-62-3 4-methyl-2-nitroaniline 
• 80477-77-6 5-Methyl-2-pyridin-2-yl-1-(2-pyridin-4-yl-ethyl)-1H-benzoimidazole 

Downstream Products

• 80477-76-5 5-Methyl-2-pyridin-2-yl-1-(2-pyridin-2-yl-ethyl)-1H-benzoimidazole 
• 80477-77-6 5-Methyl-2-pyridin-2-yl-1-(2-pyridin-4-yl-ethyl)-1H-benzoimidazole 

Relevant academic research and scientific papers

Two new Cu(II) dipeptide complexes based on 5-methyl-2-(2′-pyridyl)benzimidazole as potential antimicrobial and anticancer drugs: Special exploration of their possible anticancer mechanism

In the search for more effective anticancer drugs with less toxic side effects, dipeptides were introduced into the Cu(II) complex of 5-methyl-2-(2′-pyridyl)benzimidazole (HPBM). Analytical and spectroscopic techniques were employed to thoroughly characterize complexes [Cu(Gly-gly)(HPBM)(H2O)]ClO4·0.5H2O (1) and [Cu(Gly-L-leu)(HPBM)(H2O)]ClO4 (2) (where Gly-gly = Glycyl-glycine anion, Gly-L-leu = Glycyl-l-leucine anion). The solution stability studies performed by ultraviolet–visible (UV–Vis) spectroscopy confirmed the stability of the complexes in the buffer solutions. The DNA binding affinity was evaluated using multi-spectroscopy, viscosity measurement and molecular docking methods and further quantified by Kb and Kapp values, revealing an intercalative mode. Moreover, gel electrophoresis analysis revealed that the complexes could damage CT DNA through a hydroxyl radical pathway in the presence of ascorbic acid. All the complexes displayed favorable antimicrobial and cytotoxic activities toward the tested microorganisms (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa) and cancer cells (A549, HeLa and PC-3). Most importantly, the possible anticancer mechanism of the complexes was explored by determining the cells morphological changes, intracellular reactive oxygen species (ROS) levels, location in mitochondria, mitochondrial membrane potentials and the expression of Bcl-2 family proteins. The results showed that the complexes could induce apoptosis in HeLa cells through an ROS-mediated mitochondrial dysfunction pathway, which was accompanied by the regulation of Bcl-2 family proteins.

Three new mixed-ligand copper(II) complexes containing glycyl-l-valine and N,N-aromatic heterocyclic compounds: Synthesis, characterization, DNA interaction, cytotoxicity and antimicrobial activity

Three novel copper(II) complexes, [Cu(Gly-l-Val)(HPBM)(H2O)]·ClO4·H2O (1), [Cu(Gly-l-Val)(TBZ)(H2O)]·ClO4 (2) and [Cu(Gly-l-Val)(PBO)(H2O)]·ClO4 (3) (Gly-l-Val?=?glycyl-l-valine anion, HPBM?=?5-methyl-2-(2′-pyridyl)benzimidazole, TBZ?=?2-(4′-thiazolyl)benzimidazole, PBO?=?2-(2′-pyridyl)benzoxazole), have been prepared and characterized with elemental analyses, conductivity measurements as well as various spectroscopic techniques. The interactions of these copper complexes with calf thymus DNA were explored using UV–visible, fluorescence, circular dichroism, thermal denaturation, viscosity and docking analyses methods. The experimental results showed that all three complexes could bind to DNA via an intercalative mode. Moreover, the cytotoxic effects were evaluated using the MTT method, and the antimicrobial activity of these complexes was tested against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. The results showed that the activities are consistent with their DNA binding abilities, following the order of 1 > 2 > 3.

Amphiphilic Dendrimer as Reverse Micelle: Synthesis, Characterization and Application as Homogeneous Organocatalyst

The core and surface terminal groups are the two main catalytic sites in a dendrimer. In most of the reported examples, the catalytic sites in dendritic catalysis are the surface terminal functional groups. This perspective article concerned with the dend

2-Substituted Imidazole and Benzimidazole Corrosion Inhibitors

Disclosed are methods of using nitrogen-containing compounds as corrosion inhibitors. The present method is used to inhibit corrosion of a metal surface in contact with an aqueous system using 2-substituted imidazoles and 2-substituted benzimidazoles, and

Titanium, zirconium and vanadium complexes of 2-(benzimidazolyl, benzothiazolyl, and benzoxazolyl) pyridine as catalyst precursors for ethylene polymerization

Dissymmetric chelating complexes of Ti, Zr and V with 2-(benzimidazolyl, benzothiazolyl, and benzoxazolyl) pyridine ligands were synthesized and characterized. After activation with methylalumoxane (MAO) in solution, these complexes could be applied as ethylene polymerization catalysts. Their activities depend on the metal and the substituents at the pyridine ring and the heterocycle. Structure-property-relationship studies revealed that the titanium and vanadium catalyst systems showed higher polymerization activities than the zirconium analogues. The benzoxazolyl moiety containing vanadium complex 29, with a methyl substituent in the 6-membered ring in meta position to the nitrogen atom in the 5-membered ring, and an unsubstituted pyridine ring showed the highest activity (1154.8 kg PE/mol cat h). The produced polyethylenes exhibited high molecular weights and broad molecular weight distributions. Obviously different active sites are generated in the course of these polymerization reactions.

Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents

Abstract Thiabendazole, already approved by FDA for oral use as an anti-fungal and anti-helminthic drug since 1967, has recently been repurposed as a vascular disrupting agent. By optimization of the structure of the lead compound, we successfully identified compound TBZ-19 and the new derivative is over 100-fold more potent than the lead compound against the growth of four different cell lines (A549, HCT-116, HepG2 and HUVECs). The most potent two candidates TBZ-07 and TBZ-19, exhibiting moderate inhibitory cell proliferation activity, were also verified as anti-angiogenesis and vascular disrupting agents. Therefore, TBZ-07 and TBZ-19 would be promising candidates with vasculature targeting activity and merit further development.

Metal-mediated inhibition of escherichia coli methionine aminopeptidase: Structure-activity relationships and development of a novel scoring function for metal-ligand interactions

We report the discovery of thiabendazole as a potent inhibitor (K 1 = 0.4 μM) of Escherichia coli methionine aminopeptidase (ecMetAP) and the synthesis and pharmacological evaluation of thiabendazole congeners with activity in the upper nanomolar range, Elucidation of the X-ray structure of ecMetAP in complex with thiabendazole and an unrelated inhibitor that was independently described by another group showed that that both compounds bind to an additional CoII ion at the entrance of the active site. This unexpected finding explains the inactivity of the compounds under in vivo conditions. It also allows us to discuss the structure-activity relationships of this series of compounds in a meaningful way, based upon docking runs with an auxiliary metal ion, We describe a new scoring function for the evaluation of metal-mediated inhibitor binding that, unlike the previously used scoring function implemented in the docking program, allows us to distinguish between active and inactive compounds, Finally, conclusions for the structure-based design of in vivo-active inhibitors of ecMetAP are drawn.

Differential antiproliferative activity of new benzimidazole-4,7-diones

Ten benzimidazole-4,7-diones were synthesized and tested in vitro on two tumor cell lines. Several compounds showed a significant antiproliferative activity on K562 cells, although to a different extent, whereas compound 1i showed a highly significant activity on SW620 cells, comparable to that of doxorubicin. Both the substituents in the quinone ring and the position of the nitrogen atom in the pyridine moiety play a crucial role for the biological activity.

ACIDIC PROPERTIES OF BENZIMIDAZOLES AND SUBSTITUENT EFFECTS. V. PROTECTION OF BENZIMIDAZOLES BY N-ALKYL BOND FORMATION USING VINYLPYRIDINES

Vinylpyridines were utilized for protection of the benzimidazole N-H bond to give 1-(2-pyridylethyl)-benzimidazoles.The reaction was found to progress smoothly when glacial acetic acid was used as a catalyst.In the alkylation of 5- or 7-substituted-2-arylbenzimidazoles with vinylpyridines, the yield decreased with increasing electron-attracting effect of the substituent groups in the benzimidazole ring.On the other hand, the removal of pyridylethyl groups by the use of aluminum chloride as a catalyst was kinetically examined; a large excess of sodium hydroxide was used for decomposition of the intermediate adduct of aluminum chloride.The rate increased somewhat when electron-releasing substituent groups were present in the benzimidazole ring. 1--2-arylbenzimidazoles were resistant to removal of their (2-pyridyl)ethyl groups. 4-Vinylpyridine can be used more efficiently as a protecting agent.Keywords: 2-pyridylbenzimidazoles; protection with vinylpyridines for imidazole; 1-(2-pyridylethyl)-benzimidazoles; substituent effect on N-alkylation of benzimidazoles; rate of removal of pyridylethyl groups by aluminum chloride catalyst