36783-89-8

Upstream product

• 98-86-2 acetophenone 
• 1074-12-0 phenylglyoxal hydrate 
• 555-16-8 4-nitrobenzaldehdye 
• 670-95-1 4-Phenylimidazole 
• 586-78-7 para-nitrophenyl bromide 
• 5555-32-8 N-(cyanomethyl)-4-nitrobenzamide 
• 98-80-6 phenylboronic acid 
• 122-04-3 4-nitro-benzoyl chloride 

Downstream Products

• 1210045-67-2 2-(4-nitrophenyl)-1,4-diphenyl-1H-imidazole 

Relevant academic research and scientific papers

Nickel-Catalyzed Construction of 2,4-Disubstituted Imidazoles via C–C Coupling and C?N Condensation Cascade Reactions

A convenient Ni(II)-catalyzed C?C and C?N cascade coupling reaction was developed to directly access various 2,4-disubstituted imidazoles. The reaction scope covers a variety of aryl and aliphatic substitutions, which demonstrate moderate-to-excellent yie

Modular Synthesis of Di- A nd Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors

A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol, followed by bromination and Suzuki coupling in the imidazole ring to yield trisubstituted NH-imidazoles (23%-69%, three steps). This approach was also employed in the synthesis of known inhibitor GSK3037619A.

Anticonvulsant activity of 2,4(1H)-diarylimidazoles in mice and rats acute seizure models

2,4(1H)-Diarylimidazoles have been previously shown to inhibit hNa V1.2 sodium (Na) channel currents. Since many of the clinically used anticonvulsants are known to inhibit Na channels as an important mechanism of their action, these compounds were tested in two acute rodent seizure models for anticonvulsant activity (MES and scMet) and for sedative and ataxic side effects. Compounds exhibiting antiepileptic activity were further tested to establish a dose response curve (ED50). The experimental data identified four compounds with anticonvulsant activity in the MES acute seizure rodent model (compound 10, ED50 = 61.7 mg/kg; compound 13, ED 50 = 46.8 mg/kg, compound 17, ED50 = 129.5 mg/kg and compound 20, ED50 = 136.7 mg/kg). Protective indexes (PI = TD 50/ED50) ranged from 2.1 (compound 10) to greater than 3.6 (compounds 13, 17 and 20). All four compounds were shown to inhibit hNa V1.2 in a dose dependant manner. Even if a correlation between sodium channel inhibition and anticonvulsant activity was unclear, these studies identify four Na channel antagonists with anticonvulsant activity, providing evidence that these derivatives could be potential drug candidates for development as safe, new and effective antiepileptic drugs (AEDs).

Synthesis and biological screening of di- and trisubstituted imidazoles

Disubstituted imidazoles were prepared by reacting appropriate phenylglyoxal with different aryl aldehydes in the presence of ammonium acetate. Trisubstituted imidazoles were prepared by reacting disubstituted imidazoles with chlorobenzene in the presence

Efficient and practical synthesis of 4(5)-aryl-1H-imidazoles and 2,4(5)-diaryl-1H-imidazoles via highly selective palladium-catalyzed arylation reactions

(Chemical Equation Presented) 4(5)-Aryl-1H-imidazoles can be efficiently and selectively prepared by PdCl2(dppf)-catalyzed Suzuki-Miyaura reaction of commercially available 4(5)-bromo-1H-imidazole with arylboronic acids under phase-transfer conditions. On the other hand, N-unprotected 4(5)-aryl-1H-imidazoles can undergo highly selective Pd(OAc)2- catalyzed and CuI-mediated direct C-2-arylation with a variety of aryl bromides and iodides under base-free and ligandless conditions to produce 2,4(5)-diaryl-1H-imidazoles in modest to good yields. No N-arylation byproducts are observed under the experimental conditions used to prepare 2,4(5)-diaryl-1H-imidazoles.

A practical synthesis of 2,4(5)-diarylimidazoles from simple building blocks

(Chemical Equation Presented) A simple and efficient approach to selectively obtain 2,4(5)-diarylimidazoles suppressing formation of 2-aroyl-4(5)-arylimidazoles is described. The yield of each of the two products strongly depends on the reaction condition