6504-09-2

Usage

Structure

Benzimidazole derivative with a methylpyridine moiety attached to the benzimidazole core.

Potential uses

Pharmaceutical industry (development of drugs targeting specific receptors or enzymes), materials science, synthesis of heterocyclic compounds.

Note

Exact properties and potential uses may vary depending on specific application and context.

Upstream product

• 108-48-5 2,6-dimethylpyridine 
• 88-74-4 2-nitro-aniline 
• 95-54-5 1,2-diamino-benzene 
• 934-60-1 6-methyl-2-pyridinecarboxylic acid 
• 1122-72-1 6-methyl-2-pyridinecarboxaldehyde 

Downstream Products

• 1346678-89-4 (2-(2-benzimidazolyl)-6-methylpyridine)(1,4-bis(diphenylphosphino)butane)copper(I)(ClO₄) 
• 1346678-86-1 (2-(2-benzimidazolyl)-6-methylpyridine)(PPh₃)copper(I)(ClO₄) 
• 1384843-40-6 C₃₁H₂₆BrCuN₃P 

Relevant academic research and scientific papers

LANTHIONINE C-LIKE PROTEIN 2 LIGANDS, CELLS PREPARED THEREWITH, AND THERAPIES USING SAME

Provided are compounds that target the lanthionine synthetase C-like protein 2 pathway. The compounds can be used to treat a number of conditions, including autoimmune diseases, inflammatory diseases, chronic inflammatory diseases, diabetes, and infectiou

Synthesis of pyridinyl-benzo[d]imidazole/pyridinyl-benzo[d]thiazole derivatives and their yeast glucose uptake activity in vitro

Background: Diabetes is the primary cause of fatality and disability all over the world, in recent past, we have reported various classes of compounds as anti-glycating agents and we have also reported benzimidazole and benzothiazole derivatives as a potential class of anti-glycating agents. This encouraged us to evaluate the pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 for yeast glucose uptake activity. Methods: In the present study, an equimolar mixture of pyridine carboxaldehyde derivatives (1 mmol) and sodium metabisulphite (1 mmol) in DMF (10 mL) was stirred for 10 to 15 min, followed by addition of o-phenylene diamine/2-aminothiophenol (1 mmol) into it and refluxed for 3 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was poured into crushed ice. Precipitates were formed which were collected by filtration to produce compounds 1-27 in good yields. Recrystallization from methanol yielded pure crystals. Results: Our present study showed that all compounds showed a varying degree of yeast glucose uptake activity in the range IC50 = 36.43-272.20 μM, compared to standard metronidazole (IC50 = 41.86 ± 0.09 μM). Compounds 5 (IC50 = 38.14 ± 0.17 μM), 6 (IC50 = 40.23 ± 0.20 μM), and 7 (IC50 = 36.43 ± 0.02 μM) showed an excellent yeast glucose uptake activity better than the standard. Conclusion: Pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 were synthesized, structurally characterized, and evaluated for in vitro yeast glucose uptake activity. Compounds 5 (IC50 = 38.14 ± 0.17 μM), 6 (IC50 = 40.23 ± 0.20 μM), and 7 (IC50 = 36.43 ± 0.02 μM) demonstrated potent yeast glucose uptake activity as compared to standard metronidazole (IC50 = 41.86 ± 0.09 μM). This study identified a number of potential lead molecules which can be helpful in lowering the blood glucose level in hyperglycemia.

Synthesis, Characterization and Catalytic Application of Pyridine-Bridged N-Heterocyclic Carbene–Ruthenium Complexes in the Hydrogenation of Carbonates

A series of bulky pyridine-bridged NHC–Ru complexes have been rationally designed and synthesized; these exhibited very high catalytic activity in the hydrogenation of cyclic and linear carbonates under mild reaction conditions. In the presence of catalytic amounts of a weak base, a broad range of substrates with different ring size and steric bulk were well tolerated, providing methanol and the corresponding diols in excellent yields with a catalyst loading as low as 0.5 mol %.

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.

Iron sulfide catalyzed redox/condensation cascade reaction between 2-amino/hydroxy nitrobenzenes and activated methyl groups: A straightforward atom economical approach to 2-hetaryl-benzimidazoles and -benzoxazoles

Iron sulfide generated in situ from elemental sulfur and iron was found to be highly efficient in catalyzing a redox/condensation cascade reaction between 2-amino/hydroxy nitrobenzenes and activated methyl groups. This method represents a straightforward and highly atom economical approach to 2-hetaryl-benzimidazoles and -benzoxazoles.

MODIFIED METHOD FOR THE SYNTHESIS OF 2-HETEROARYL-SUBSTITUTED IMIDAZOPYRIDINES AND BENZIMIDAZOLE

A method is proposed for the production of 2-heteroarylimidazopyridines and benzimidazole, based on the oxidation of o-nitroaminopyridine or o-nitroaniline and heteroaromatic compounds with an active methyl group by elemental sulfur.

Synthesis and antiinflammatory activity of some 2-(substituted-pyridinyl)benzimidazoles

A series of 2-(2-pyridinyl)benzimidazoles was synthesized and evaluated for antiinflammatory activity by the carrageenan-induced rat paw edema assay. Among several active derivatives, 2-(5-ethylpyridin-2-yl)benzimidazole was selected for further study. A comparison of this compound with phenylbutazone and tiaramide revealed that it possesses stronger activity in acute inflammatory models possibly with slightly less gastrointestinal irritation than both phenylbutazone and tiaramide.