41384-83-2

Usage

Uses

Used in Pharmaceutical Industry:
4-NITRO-1-PHENYLIMIDAZOLE is used as a chemical intermediate for the synthesis of pharmaceuticals, contributing to the development of new drugs and improving existing medications.
Used in Organic Compounds Synthesis:
4-NITRO-1-PHENYLIMIDAZOLE is utilized as an intermediate in the synthesis of organic compounds, playing a crucial role in the creation of various chemical products.
Used in Dye and Pigment Production:
4-NITRO-1-PHENYLIMIDAZOLE is employed in the production of dyes and pigments, enhancing the color properties and performance of these products.
However, it is important to note that 4-Nitro-1-phenylimidazole is known to be toxic and can cause irritation to the skin, eyes, and respiratory system upon exposure. Its potential environmental impact is not well documented, but it is considered to be harmful to aquatic organisms, necessitating careful handling and disposal to minimize ecological risks.

InChI:InChI=1/C9H7N3O2/c13-12(14)9-6-11(7-10-9)8-4-2-1-3-5-8/h1-7H

Upstream product

• 62-53-3 aniline 
• 71100-56-6 1-(p-toluenesulfonyl)-4-nitroimidazole 
• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 
• 6293-66-9 diphenyliodonium p-toluenesulfonate 
• 591-50-4 iodobenzene 
• 19182-81-1 1,4-dinitro-1H-imidazole 

Downstream Products

• 152483-39-1 5-amino-4-nitro-1-phenylimidazole 
• 83325-36-4 N-(1-phenyl-1H-imidazol-4-yl)-acetamide 
• 90946-05-7 N-(1-phenyl-1H-imidazol-4-yl)-formamide 
• 268538-46-1 phenyl (1-phenyl-1H-imidazol-4-yl)carbamate 
• 1821666-85-6 1-phenyl-1H-imidazole-4-amine hydrochloride 
• 95862-41-2 (3-methyl-5-nitro-3H-imidazol-4-yl)-phenyl-amine 
• 87243-12-7 4⁽⁵⁾-Nitro-5⁽⁴⁾-phenylaminoimidazole 
• 318513-66-5 3-phenyl-5-imidazolidinone 
• 103-01-5 N-Phenylglycine 
• 158688-63-2 1-phenyl-1H-imidazol-4-amine 
• 178695-68-6 1-phenyl-4-oximinoimidazolidine 

Relevant academic research and scientific papers

WDR5-MYC INHIBITORS

Substituted N-heteroaryl sulfonamide compounds inhibit WDR5-MYC interactions, and the compounds and their pharmaceutical compositions are useful for treating disorders and conditions in a subject such as cancer cell proliferation.

COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH STING ACTIVITY

This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt, and/or hydrate, and/or cocrystal, and/or drug combination of the compound) that inhibit (e.g., antagonize) Stimulator of Interferon Genes (STING). Said chemical entities are useful, e.g., for treating a condition, disease or disorder in which increased (e.g., excessive) STING activation (e.g., STING signaling) contributes to the pathology and/or symptoms and/or progression of the condition, disease or disorder (e.g., cancer) in a subject (e.g., a human). This disclosure also features compositions containing the same as well as methods of using and making the same.

Discovery of WD Repeat-Containing Protein 5 (WDR5)-MYC Inhibitors Using Fragment-Based Methods and Structure-Based Design

The frequent deregulation of MYC and its elevated expression via multiple mechanisms drives cells to a tumorigenic state. Indeed, MYC is overexpressed in up to ?50% of human cancers and is considered a highly validated anticancer target. Recently, we discovered that WD repeat-containing protein 5 (WDR5) binds to MYC and is a critical cofactor required for the recruitment of MYC to its target genes and reported the first small molecule inhibitors of the WDR5-MYC interaction using structure-based design. These compounds display high binding affinity, but have poor physicochemical properties and are hence not suitable for in vivo studies. Herein, we conducted an NMR-based fragment screening to identify additional chemical matter and, using a structure-based approach, we merged a fragment hit with the previously reported sulfonamide series. Compounds in this series can disrupt the WDR5-MYC interaction in cells, and as a consequence, we observed a reduction of MYC localization to chromatin.

Structure-Based Design of 6-Chloro-4-aminoquinazoline-2-carboxamide Derivatives as Potent and Selective p21-Activated Kinase 4 (PAK4) Inhibitors

Herein, we report the discovery and characterization of a novel class of PAK4 inhibitors with a quinazoline scaffold. Based on the shape and chemical composition of the ATP-binding pocket of PAKs, we chose a 2,4-diaminoquinazoline series of inhibitors as a starting point. Guided by X-ray crystallography and a structure-based drug design (SBDD) approach, a series of novel 4-aminoquinazoline-2-carboxamide PAK4 inhibitors were designed and synthesized. The inhibitors' selectivity, therapeutic potency, and pharmaceutical properties were optimized. One of the best compounds, 31 (CZh226), showed remarkable PAK4 selectivity (346-fold vs PAK1) and favorable kinase selectivity profile. Moreover, this compound potently inhibited the migration and invasion of A549 tumor cells by regulating the PAK4-directed downstream signaling pathways in vitro. Taken together, these data support the further development of 31 as a lead compound for PAK4-targeted anticancer drug discovery and as a valuable research probe for the further biological investigation of group II PAKs.

Identification of Aminoimidazole and Aminothiazole Derivatives as Src Family Kinase Inhibitors

Src family kinases (SFKs) are a family of non-receptor tyrosine kinases (TKs) implicated in the regulation of many cellular processes. The aberrant activity of these TKs has been associated with the growth and progression of cancer. In particular, c-Src i

Magnetic nano-Fe3O4 supported ionic liquids: A recoverable phase transfer catalyst for c-n cross coupling reaction

Magnetic nanoparticles-supported quaternary ammonium salts were prepared and evaluated as phase transfer catalysts. Some of them exhibited good activities in CuCl-catalyzed N-arylation of aryl amines and N-heterocycles with aryl iodides in aqueous solution without any ligands. They could be readily separated from reaction solution using an external magnet and reused three times with a little loss in activity.

1-Aryl-4-nitro-1H-imidazoles, a new promising series for the treatment of human African trypanosomiasis

Nitroimidazoles are a well-known class of antibacterial and antiprotozoal drugs but in spite of the widespread clinical and veterinary use of these drugs, this family has been stigmatized in part due to associated genotoxicity problems. Here we report the synthesis, the anti-trypanosomal activity and a structure-activity relationship (SAR) study of a series of about fifty 1-aryl-4-nitro-1H-imidazoles, with an emphasis on selected in vivo active molecules. Compounds 4-nitro-1-{4-(trifluoromethoxy)phenyl}-1H-imidazole and 1-(3,4-dichlorophenyl)-4-nitro-1H-imidazole are curative in mouse models of both acute and chronic African trypanosomiasis when given orally at doses of 25-50 mg/kg for 4 days for the acute infection, and 50-100 mg/kg (bid) for 5 days in the chronic model. While both compounds are bacterial mutagens, activity is lost in strains lacking bacterial specific nitro-reductases. Mammalian nitro-reductases do not reduce nitroaromatic compounds with low redox potentials with same avidity as their bacterial counterparts and these compounds were shown to be devoid of genotoxicity in mammalian cells. Both compounds are promising leads for the treatment of human African trypanosomiasis (HAT or sleeping sickness), including the fatal stage 2 of the disease, for which new treatments are urgently needed.

Regioselective N-arylation of nitroazoles. Determination of the structure of N-arylnitro-azoles on the basis of NMR spectroscopic data and quantum-chemical calculations

The N-arylation of a series of nitroazoles has been studied with the aid of diaryliodonium salts in the presence of CuI under the action of microwave radiation. It was found that alkylation proceeds regioselectively in each actual case with the formation

Novel orally active NPY Y5 receptor antagonists: Synthesis and structure-activity relationship of spiroindoline class compounds

Spiroindoline urea derivatives, designed to act as NPY Y5 receptor antagonists, were synthesized and their structure-activity relationships were investigated. Of these derivatives, compound 3a showed good Y5 binding affinity with favorable pharmacokinetic

Facile synthesis of fluorinated 1-desazapurines

A preparative approach towards 1-desazapurines, starting from 4(5)-aminoimidazoles and polyfluoroalkyl-containing 1,3-CCC-biselectrophiles was developed. As a result, a set of fluorinated 1-desazapurines was synthesized. Additionally, a synthetic route to 1-desazapurines bearing a sugar-mimicking group is proposed. Georg Thieme Verlag Stuttgart.