46503-52-0

Basic information

• Product Name: 1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOLE-1-YL) ETHANONE
• Synonyms: AURORA KA-666;1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)ETHANONE;1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOLE-1-YL) ETHANONE;1-(2,4-DICHLOROPHENYL)-2-IMIDAZOL-1-YL-ETHANONE;2',4'-DICHLORO-2-IMIDAZOLYLACETOPHENONE;2'-(1H-IMIDAZOLE-1-YL)-2,4-DICHLOROACETOPHENONE;1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-one;2,4'-Dichloro Phenyl-2-Imidazole-1-Ethanone
• CAS NO: 46503-52-0
• Molecular Formula: C₁₁H₈Cl₂N₂O
• Molecular Weight: 255.1
• EINECS: 256-273-3
• Mol File: 46503-52-0.mol
• Article Data: 38

Chemical Properties

• Melting Point: 76-78 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 441.1 °C at 760 mmHg
• Flash Point: 220.6 °C
• Appearance: Off-white solid
• Density: 1.38 g/cm³
• PKA: 5.97±0.10(Predicted)
• CAS DataBase Reference: 1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOLE-1-YL) ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOLE-1-YL) ETHANONE(46503-52-0)
• EPA Substance Registry System: 1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOLE-1-YL) ETHANONE(46503-52-0)

Safety Data

• Hazardous Substances Data: 46503-52-0(Hazardous Substances Data)

Usage

General Description

The chemical 1-(2,4-dichlorophenyl)-2-(1H-imidazole-1-yl) ethanone is a white to off-white powder that is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is a ketone compound that contains a dichlorophenyl group and an imidazole ring. This chemical is often used as a building block in the production of antifungal, antibacterial, and anti-inflammatory drugs. It is also utilized in the development of new chemical entities for various therapeutic applications. Additionally, it may have potential uses as a pesticide and in other industrial applications.

Upstream product

• 288-32-4 1H-imidazole 
• 4252-78-2 2,2',4'-trichloroacetophenone 
• 541-73-1 1,3-Dichlorobenzene 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 7732-18-5 water 
• 78344-77-1 2-diazo-1-(2,4-dichlorophenyl)ethanone 
• 2631-72-3 2,4-dichlorophenacyl bromide 

Downstream Products

• 104061-06-5 1-[2-(2,4-dichlorophenyl)-2-(4-phenyl-piperazine)vinyl]-1H-imidazole 
• 70827-17-7 1-[2-hydroxy-2-(2,4-dichlorophenyl)hexyl]imidazole 
• 78202-20-7 α-t-butyl-α-(o,p-dichlorophenyl)-1H-imidazole-1-ethanol 
• 85473-16-1 2-(2,4-Dichloro-phenyl)-1-imidazol-1-yl-heptan-2-ol 
• 85473-17-2 2-(2,4-dichlorophenyl)-1-(1-imidazolyl)-octan-2-ol 
• 78202-27-4 2-(2,4-Dichloro-phenyl)-1-imidazol-1-yl-decan-2-ol 
• 78202-28-5 2-(2,4-Dichloro-phenyl)-1-imidazol-1-yl-dodecan-2-ol 
• 78202-37-6 1-[[2-(2,4-dichlorophenyl)-oxiranyl]methyl]-1H-imidazole 
• 78202-21-8 2-(2,4-Dichloro-phenyl)-1-imidazol-1-yl-3-methyl-butan-2-ol 
• 85473-12-7 2-(2,4-Dichloro-phenyl)-1-imidazol-1-yl-propan-2-ol 
• 24155-42-8 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol 
• 116791-38-9 1-(2-(2,4-dichlorophenyl)-2-(3-hydroxypropylamino)ethyl)-1H-imidazole 
• 64211-06-9 (Z)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanone oxime 
• 152913-51-4 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone, 2,4-dichlorophenylhydrazone, hydrochloride 

Relevant articles and documents

BuChE-IDO1 inhibitor as well as preparation method and application thereof

The invention relates to the field of medicines, and particularly discloses a BuChE-IDO1 inhibitor as well as a preparation method and application thereof. The 7-chlorine-3-substituted benzothiophene part of sertaconazole is chemically modified, the influence of the 7-chlorine-3-substituted benzothiophene part of sertaconazole on the in-vitro inhibitory activity of AChE, BuChE and IDO1 is explored, the target compound is further optimized, and the technical problems that an existing BuChE-IDO1 inhibitor is poor in pertinence and safety are solved. What is explored is that an appropriate substituent group introduced to a 2-benzothiazole ring can form additional interaction with surrounding amino acids and heme iron, so that the binding affinity of the analogue with BuChE and IDO1 is increased, and a new idea is broadened for more efficient and targeted treatment of advanced AD diseases.

Lead optimization generates selenium-containing miconazole CYP51 inhibitors with improved pharmacological profile for the treatment of fungal infections

A series of selenium-containing miconazole derivatives were identified as potent antifungal drugs in our previous study. Representative compound A03 (MIC = 0.01 μg/mL against C.alb. 5314) proved efficacious in inhibiting the growth of fungal pathogens. However, further study showed lead compound A03 exhibited potential hemolysis, significant cytotoxic effect and unfavorable metabolic stability and was therefore modified to overcome these drawbacks. In this article, the further optimization of selenium-containing miconazole derivatives resulted in the discovery of similarly potent compound B17 (MIC = 0.02 μg/mL against C.alb. 5314), exhibiting a superior pharmacological profile with decreased rate of metabolism, cytotoxic effect and hemolysis. Furthermore, compound B17 showed fungicidal activity against Candida albicans and significant effects on the treatment of resistant Candida albicans infections. Meanwhile, compound B17 not only could reduce the ergosterol biosynthesis pathway by inhibiting CYP51, but also inhibited biofilm formation. More importantly, compound B17 also shows promising in vivo efficacy after intraperitoneal injection and the PK study of compound B17 was evaluated. In addition, molecular docking studies provide a model for the interaction between the compound B17 and the CYP51 protein. Overall, we believe that these selenium-containing miconazole compounds can be further developed for the potential treatment of fungal infections.

Design and Synthesis of Tetrazole- And Pyridine-Containing Itraconazole Analogs as Potent Angiogenesis Inhibitors

Itraconazole, a widely used antifungal drug, was found to possess antiangiogenic activity and is currently undergoing multiple clinical trials for the treatment of different types of cancer. However, it suffers from extremely low solubility and strong interactions with many drugs through inhibition of CYP3A4, limiting its potential as a new antiangiogenic and anticancer drug. To address these issues, a series of analogs in which the phenyl group is replaced with pyridine or fluorine-substituted benzene was synthesized. Among them the pyridine- and tetrazole-containing compound 24 has significantly improved solubility and reduced CYP3A4 inhibition compared to itraconazole. Similar to itraconazole, compound 24 inhibited the AMPK/mTOR signaling axis and the glycosylation of VEGFR2. It also induced cholesterol accumulation in the endolysosome and demonstrated binding to the sterol-sensing domain of NPC1 in a simulation study. These results suggested that compound 24 may serve as an attractive candidate for the development of a new generation of antiangiogenic drug.