53458-08-5

Usage

InChI:InChI=1/C16H14N2O/c1-19-14-9-7-12(8-10-14)15-11-17-16(18-15)13-5-3-2-4-6-13/h2-11H,1H3,(H,17,18)

Upstream product

• 100-52-7 benzaldehyde 
• 1076-95-5 p-methoxyphenylglyoxal 
• 93435-57-5 α-tosyloxy-p-methoxyacetophenone 
• 618-39-3 benzamidin 
• 768-60-5 4-methoxyphenylacetylen 
• 100-51-6 benzyl alcohol 
• 104-01-8 4-Methoxyphenylacetic acid 
• 637-69-4 4-Methoxystyrene 
• 1670-14-0 benzamidine monohydrochloride 
• 22013-86-1 1-(2-bromo-2-nitrovinyl)-4-methoxybenzene 
• 1456-22-0 3-phenyl-4H-[1,2,4]oxadiazol-5-one 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 1443145-38-7 2-[4-(4-methoxy-phenyl)-2-phenyl-imidazol-1-yl]-1-(4-pyridin-2-yl-piperazin-1-yl)-ethanone 

Relevant academic research and scientific papers

Preparation of Imidazole Derivatives via Bisfunctionalization of Alkynes Catalyzed by Ruthenium Carbonyl

A one-step, oxidative bisfunctionalization of alkynes to generate cis -enediol diacetates catalyzed by ruthenium carbonyl (triruthenium dodecacarbonyl) is presented. The reaction was performed using the alkyne, (diacetoxyiodo)benzene, Ru 3 (CO) 12 as the catalyst, and toluene as the solvent at 100 °C to give the cis -enediol diacetates in up to 82percent yields. This method overcomes the shortcomings of existing methods, such as tedious reaction steps, substrate limitations, and the use of toxic reagents. Furthermore, the reaction of module cis -enediol diacetates with ammonium carbonate [(NH 4) 2 CO 3 ] in an alcohol solvent gave imidazole derivatives in 37-84percent yields, thus providing a simple and mild new method for the synthesis of imidazole compounds.

Copper-Catalyzed Simultaneous Activation of C-H and N-H Bonds: Three-Component One-Pot Cascade Synthesis of Multi?-substituted Imidazoles

A copper-catalyzed expedient, practical, and straightforward approach for the one-pot three-component modular synthesis of multisubstituted imidazoles has been described by using arylacetic acids, N -arylbenzamidines, and nitroalkanes. The reaction involv

One-Pot Protocol for the Synthesis of Imidazoles and Quinoxalines using N-Bromosuccinimide

N-bromosuccinimide (NBS)-mediated one-pot, green, efficient and practical synthesis of substituted imidazoles and quinoxalines has been achieved by the reaction of styrenes with N-arylbenzamidines and o-phenylenediamines, respectively, in a water:1,4-dioxane mixture. The reaction involves formation of an α-bromo ketone as an intermediate in the presence of NBS and water, followed by condensation with the N-arylbenzamidine and o-phenylenediamine. Use of an inexpensive NBS as a bromine source as well as an oxidant, water as a solvent and readily available starting materials makes this protocol environmentally benign and economically viable. Substituted imidazoles and quinoxalines were obtained in good to excellent yields with wide functional group compatibility. (Figure presented.).

Imidazoles from nitroallylic acetates and α-bromonitroalkenes with amidines: Synthesis and trypanocidal activity studies

Cascade reactions of amidines with nitroallylic acetates and α-bromonitroalkenes provide potentially bioactive imidazoles in good to excellent yields in most cases. While 2,4-disubstituted imidazol-5-yl acetates are formed in the first case, 2,4-disubstituted imidazoles, bearing no substituent at position 5, are the products in the second case. These two series of imidazoles, viz. 2,4,5-trisubstituted and 2,4-disubstituted, were screened for their activity against the protozoan parasite Trypanosoma cruzi which is responsible for Chagas disease. As many as three compounds were as active as the standard benznidazole and two others were 2-3-fold more active highlighting the potential of substituted imidazoles, easily accessible from nitroalkenes, as possible anti-parasitic agents.

Synthesis of Imidazoles and Pyrimidines Using Palladium-Catalyzed Decarboxylative Intramolecular Condensation of 1,2,4-Oxadiazol-5(4 H)-ones

We found that 1,2,4-oxadiazol-5(4H)-ones acted as iminonitrene equivalents in the presence of a palladium catalyst and a stoichiometric amount of phosphine and that aza-Wittig-type condensation with the internal carbonyl moiety occurred to afford the corresponding imidazoles and pyrimidines. Georg Thieme Verlag Stuttgart. New York.

A facile and eco-friendly synthesis of diarylthiazoles and diarylimidazoles in water

A simple, efficient and high yielding greener protocol for the synthesis of substituted thiazoles and imidazoles is described that utilizes the reaction of readily available α-tosyloxy ketones with variety of thioamides/amidines in water.

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).

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

METHOD OF TREATING CONDITIONS SUSCEPTIBLE TO MODULATION OF NPY RECEPTORS WITH DIARYLIMIDAZOLE DERIVATIVES

Certain diaryl imidazoles act as partial agonists or antagonists for NPY receptors, in particular NPY 5 receptors. They are of use, for example in treating loss of appetite. Such compounds bear aryl groups in the 2 position. Many of the compounds are novel.

Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles

A number of trisubstituted imidazoles were made and several found to be potent antiinflammatory agents when examined in the carrageenan rat paw edema test. The antiinflammatory activity of these compounds is retained in adrenalectomized rats. Unlike many previously reported antiinflammatory agents, these compounds are extremely weak acids pK[a] ≥ 11) and are therefore not ionized at physiological pH. One compound, 4,5 bis (4 methoxyphenyl) 2 trifluoromethylimidazole (flumizole), is more potent than indometacin in the rat paw edema test and, in contrast to some related compounds, does not cause photosensitization in mice.