73225-15-7

Usage

Uses

Used in Pharmaceutical Research:
2-METHYL-1-(4-NITROPHENYL)-1H-IMIDAZOLE is used as a research compound for its potential biological activity, which includes anti-inflammatory and anticancer properties. It is studied for its ability to modulate various biological pathways and mechanisms, contributing to its potential as a therapeutic agent.
Used in Anticancer Applications:
In the field of oncology, 2-METHYL-1-(4-NITROPHENYL)-1H-IMIDAZOLE is used as an anticancer agent, being investigated for its effects on tumor growth and progression. Its potential to target and inhibit cancer cells makes it a candidate for further development in cancer treatment.
Used in Antimicrobial Applications:
2-METHYL-1-(4-NITROPHENYL)-1H-IMIDAZOLE is also used as an antimicrobial agent, given its potential to combat various microorganisms. This property is valuable in the ongoing search for new antibiotics and antifungal agents to address the growing issue of antibiotic resistance.
Used in Drug Development:
In the pharmaceutical industry, 2-METHYL-1-(4-NITROPHENYL)-1H-IMIDAZOLE is used as a lead compound in the development of new drugs and pharmaceutical products. Its diverse chemical properties and potential biological activities make it a promising candidate for the creation of innovative therapeutics.

Upstream product

• 693-98-1 2-methylimidazole 
• 350-46-9 4-Fluoronitrobenzene 
• 586-78-7 para-nitrophenyl bromide 
• 100-00-5 4-chlorobenzonitrile 
• 636-98-6 p-nitrobenzene iodide 
• 24067-17-2 4-nitrophenylboronic acid 

Downstream Products

• 21722-04-3 1-(p-nitrophenyl)-2-methyl-5-nitroimidazole 
• 21721-92-6 Nitrefazole 
• 74852-81-6 4-(2-methyl-1H-imidazol-1-yl)benzenamine 
• 189298-29-1 [4-(2-Methyl-imidazol-1-yl)-phenyl]-hydrazine 
• 1312099-59-4 1-(4-bromophenyl)-2-methyl-1H-imidazole 
• 1312098-88-6 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazole 

Relevant academic research and scientific papers

N-Heterocyclic Carbene Copper(I) Complex Catalyzed Coupling of (Hetero)aryl Chlorides and Nitrogen Heterocycles: Highly Efficient Catalytic System

A highly efficient catalytic system for the N-arylation reactions of (hetero)aryl chlorides and nitrogen heterocycles with a copper(I) complex containing a 1,10-phenanthroline analogue N-heterocyclic carbene (NHC) has been reported. The complex was characterized by 1H NMR and 13C NMR spectroscopy and elemental analysis, and its structure was determined by single-crystal X-ray diffraction. The NHC-copper(I) complex was employed as pre-catalyst for Ullmann type N-arylation reactions of (hetero)aryl chlorides with various azoles. A variety of hindered and functionalized azoles and (hetero)aryl chlorides were transformed in good to excellent yields.

Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation

In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.

α-d-Galacturonic Acid as Natural Ligand for Selective Copper-Catalyzed N-Arylation of N-Containing Heterocycles

The first application of α-d-galacturonic acid hydrate (GalA) is reported here, as a potential O-donor ligand. The C-N couplings of N-heterocycles with aryl halides or arylboronic acids could be readily conducted and exhibited good functional group tolerance with characters of selectivity. These N-Arylazoles allow rapid access to several pharmaceutical intermediates and can be easily transformed into a variety of other interesting scaffolds as well.

L -(-) -Quebrachitol as a Ligand for Selective Copper(0)-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles

l-(-)-Quebrachitol (QCT) has been found as a ligand of copper powder for selective N-arylation of nitrogen-containing heterocycles with aryl halides. Furthermore, another potential catalytic system (copper powder/QCT/t-BuOK) was successfully adapted to unactivated aryl chlorides.

Functional 1,8-naphthyridine copper(I) complex as efficient catalyst for n-arylation of imidazoles coupling reactions

The functional 1,8-naphthyridine copper(I) complex, synthesized through a non-catalyst C(sp3)-H methylenation, catalyzes the cross-coupling reaction of aryl halides with imidazoles, by C?N bond formation. The Cu(I) complex catalyzes the reaction with a low catalyst loading (1%, molar fraction) and cheap base even under aerobic conditions. The procedure tolerates aryl halides with various functional groups (such as methyl, methoxy, acetyl, fluoro, nitrile and nitro groups) and gives the corresponding coupling products in moderate to high yields.

N-ARYLATED ANALOGUES AND USES THEREOF

The present invention provides novel compounds of Formula (I′) and (I), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, prodrugs, and compositions thereof. Als

Antimicrobial peptide-inspired NH125 analogues: Bacterial and fungal biofilm-eradicating agents and rapid killers of MRSA persisters

During microbial infection, antimicrobial peptides are utilized by the immune response to rapidly eradicate microbial pathogens through the destruction of cellular membranes. Inspired by antimicrobial peptides, quaternary ammonium cationic (QAC) compounds have emerged as agents capable of destroying bacterial membranes leading to rapid bacterial death, including the eradication of persistent, surface-attached bacterial biofilms. NH125, an imidazolium cation with a sixteen membered fatty tail, was recently reported to eradicate persister cells and was our starting point for the development of novel antimicrobial agents. Here, we describe the design, chemical synthesis and biological investigations of a collection of 30 diverse NH125 analogues which provided critical insights into structural features that are important for antimicrobial activities in this class. From these studies, multiple NH125 analogues were identified to possess potent antibacterial and antifungal activities, eradicate both bacterial and fungal biofilms and rapidly eradicate MRSA persister cells in stationary phase. NH125 analogues also demonstrated more rapid persister cell killing activities against MRSA when tested alongside a panel of diverse membrane-active agents, including BAC-16 and daptomycin. NH125 analogues could have a significant impact on persister- and biofilm-related problems in numerous biomedical applications.

Mechanistic Studies on the Palladium-Catalyzed Direct C-5 Arylation of Imidazoles: The Fundamental Role of the Azole as a Ligand for Palladium

An in-depth mechanistic study on the palladium-catalyzed direct arylation of imidazoles at the C-5 position is presented. The interactions of triphenylphosphine (PPh3)-ligated aryl-Pd species with 1,2-dimethyl-1H-imidazole (dmim) have been studied in detail. In contrast with previous suggestions, phosphine-ligated organo-Pd species are not active and the reaction proceeds through imidazole-ligated organo-Pd intermediates. The kinetics of the oxidative addition of aryl halides with dmim-ligated Pd(0) species have been characterized in a Pd(dba)2/dmim model system. A thorough study of the equilibria involving novel [ArPd(dmim)2X] complexes (X=I, OAc) and the unexpected cationic [ArPd(dmim)3]+ is also reported. The ability of these species to effect the C-H arylation of dmim at room temperature in the presence of acetate is also demonstrated.

A cyano-bridged copper(II)-copper(I) mixed-valence coordination polymer as a source of copper oxide nanoparticles with catalytic activity in C-N, C-O and C-S cross-coupling reactions

A cyano-bridged copper(ii)-copper(i) mixed valence polymer, namely {[Cu4(CN)5(C5H5N)4]} n (1), was synthesized and characterized by elemental analysis, IR spectroscopy, thermogravimetric analysis, differential scanning calorimetric analysis, and single crystal X-ray crystallography. Single crystal X-ray studies show that the coordination polymer 1 is linked by the cyanide anions with μ-1κN:2κC bridging modes to the copper centers, generating a two-dimensional (2D) layered network. The coordination polymer 1, upon pyrolyzing, yielded copper oxide nanoparticles, which have been characterized by TEM and powder X-ray diffraction. The catalytic properties of the resulting copper oxide nanoparticles have also been studied in C-N, C-O, and C-S cross-coupling reactions with aryl halides. The C-N, C-O and C-S coupling products were obtained in moderate to good yields (66-90%, 72-98%, and 50-86%), respectively. the Partner Organisations 2014.

Efficient and reusable catalytic system of Cul-PEG for n-arylation of imidazoles

A simple, efficient, and recyclable catalytic system of CuI-poly(ethylene glycol) (PEG) was developed for the N-arylation of imidazoles with aryl halides to afford corresponding N-arylimidazoles in good to excellent yields under mild conditions and free of any additional ligands and solvents. The isolation of the products was readily performed by simple extraction with ether, and the catalytic system could be reused without remarkable loss of activity even after six runs.