134071-11-7

Basic information

• Product Name: 1-(2,4-DIFLUOROPHENYL)-2-(1H-IMIDAZOL-1-YL)-1-ETHANONE
• Synonyms: 1-(2,4-DIFLUOROPHENYL)-2-(1H-IMIDAZOL-1-YL)-1-ETHANONE;1-(2,4-DIFLUOROPHENYL)-2-(1H-IMIDAZOL-1-YL)-ETHANONE;1-(2,4-DIFLUORO-PHENYL)-2-IMIDAZOL-1-YL-ETHANONE
• CAS NO: 134071-11-7
• Molecular Formula: C₁₁H₈F₂N₂O
• Molecular Weight: 222.19
• Product Categories: API intermediates
• Mol File: 134071-11-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 122 °C
• Boiling Point: 401.501 °C at 760 mmHg
• Flash Point: 196.621 °C
• Appearance: /
• Density: 1.297 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.564
• PKA: 6.00±0.10(Predicted)
• CAS DataBase Reference: 1-(2,4-DIFLUOROPHENYL)-2-(1H-IMIDAZOL-1-YL)-1-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-DIFLUOROPHENYL)-2-(1H-IMIDAZOL-1-YL)-1-ETHANONE(134071-11-7)
• EPA Substance Registry System: 1-(2,4-DIFLUOROPHENYL)-2-(1H-IMIDAZOL-1-YL)-1-ETHANONE(134071-11-7)

Safety Data

• Hazardous Substances Data: 134071-11-7(Hazardous Substances Data)

Usage

General Description

1-(2,4-Difluorophenyl)-2-(1H-imidazol-1-yl)-1-ethanone is a chemical compound that belongs to the family of ketones. It is also known by the chemical name diflucortolone, which is a synthetic glucocorticoid medication used to treat skin conditions such as eczema, dermatitis, and psoriasis. 1-(2,4-DIFLUOROPHENYL)-2-(1H-IMIDAZOL-1-YL)-1-ETHANONE has a molecular formula C12H9F2N3O and a molecular weight of 255.21 g/mol. Its structure consists of a difluorophenyl group attached to an imidazole ring, with a ketone group at the end of the molecule. Diflucortolone works by reducing inflammation and suppressing the immune response in the skin, providing relief from itching, redness, and swelling associated with various skin conditions.

InChI:InChI=1/C11H8F2N2O/c12-8-1-2-9(10(13)5-8)11(16)6-15-4-3-14-7-15/h1-5,7H,6H2

Upstream product

• 288-32-4 1H-imidazole 
• 51336-94-8 2-chloro-1-(2,4-dichlorophenyl)ethanone 
• 372-18-9 1,3-Difluorobenzene 
• 364-83-0 2',4'-difluoroacetophenone 
• 102429-07-2 2-bromo-2',4'-difluoroacetophenone 

Downstream Products

• 477948-96-2 1-(2,4-difluorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol 

Relevant articles and documents

Design, synthesis, and biological evaluation of novel miconazole analogues containing selenium as potent antifungal agents

Herein, based on the theory of bioisosterism, a series of novel miconazole analogues containing selenium were designed, synthesized and their inhibitory effects on thirteen strains of pathogenic fungi were evaluated. It is especially encouraging that all the novel target compounds displayed significant antifungal activities against all tested strains. Furthermore, all the target compounds showed excellent inhibitory effects on fluconazole-resistant fungi. Subsequently, preliminary mechanistic studies indicated that the representative compound A03 had a strong inhibitory effect on C.alb. CYP51. Moreover, the target compounds could prevent the formation of fungi biofilms. Further hemolysis test verified that potential compounds had higher safety than miconazole. In addition, molecular docking study provided the interaction modes between the target compounds and C.alb. CYP51. These results strongly suggested that some target compounds are promising as novel antifungal drugs.

Novel BuChE-IDO1 inhibitors from sertaconazole: Virtual screening, chemical optimization and molecular modeling studies

In our effort towards the identification of novel BuChE-IDO1 dual-targeted inhibitor for the treatment of Alzheimer's disease (AD), sertaconazole was identified through a combination of structure-based virtual screening followed by MM-GBSA rescoring. Preliminary chemical optimization was performed to develop more potent and selective sertaconazole analogues. In consideration of the selectivity and the inhibitory activity against target proteins, compounds 5c and 5d were selected for the next study. Further modification of compound 5c led to the generation of compound 10g with notably improved selectivity towards BuChE versus AChE. The present study provided us with a good starting point to further design potent and selective BuChE-IDO1 inhibitors, which may benefit the treatment of late stage AD.

Antifungal activity, mode of action variability, and subcellular distribution of coumarin-based antifungal azoles

Azole antifungals inhibit the biosynthesis of ergosterol, the fungal equivalent of cholesterol in mammalian cells. Here we report an investigation of the activity of coumarin-substituted azole antifungals. Screening against a panel of Candida pathogens, including a mutant lacking CYP51, the target of antifungal azoles, revealed that this enzyme is inhibited by triazole-based antifungals, whereas imidazole-based derivatives have more than one mode of action. The imidazole-bearing antifungals more effectively reduced trailing growth associated with persistence and/or recurrence of fungal infections than triazole-based derivatives. The imidazole derivatives were more toxic to mammalian cells and more potently inhibited the activity of CYP3A4, which is one of the main causes of azole toxicity. Using live cell imaging, we showed that regardless of the type of azole ring fluorescent 7-diethylaminocoumarin-based azoles localized to the endoplasmic reticulum, the organelle that harbors CYP51. This study suggests that the coumarin is a promising scaffold for development of novel azole-based antifungals that effectively localize to the fungal cell endoplasmic reticulum.