78202-37-6

Basic information

• Product Name: 1-[[2-(2,4-DICHLOROPHENYL)OXIRANYL]METHYL]-1H-IMIDAZOLE
• Synonyms: AURORA KA-656;1-[[2-(2,4-DICHLOROPHENYL)OXIRANYL]METHYL]-1H-IMIDAZOLE
• CAS NO: 78202-37-6
• Molecular Formula: C₁₂H₁₀Cl₂N₂O
• Molecular Weight: 269.13
• Mol File: 78202-37-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 447.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.44±0.1 g/cm3(Predicted)
• PKA: 6.78±0.12(Predicted)
• CAS DataBase Reference: 1-[[2-(2,4-DICHLOROPHENYL)OXIRANYL]METHYL]-1H-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[[2-(2,4-DICHLOROPHENYL)OXIRANYL]METHYL]-1H-IMIDAZOLE(78202-37-6)
• EPA Substance Registry System: 1-[[2-(2,4-DICHLOROPHENYL)OXIRANYL]METHYL]-1H-IMIDAZOLE(78202-37-6)

Safety Data

• Hazardous Substances Data: 78202-37-6(Hazardous Substances Data)

Usage

Class

Imidazole class of compounds

Usage

Pharmaceutical and agricultural products

Function

Antifungal properties

Mechanism

Interferes with the growth and reproduction of fungi

Applications

Treatment for fungal infections in humans, animals, and plants

Chemical Structure

Imidazole ring with a 2,4-dichlorophenyl group and an oxiranyl methyl substituent

Importance

Valuable tool in the fight against fungal diseases

Upstream product

• 1774-47-6 trimethylsulfoxonium iodide 
• 46503-52-0 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone 
• 83338-21-0 2-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-1,2-propanediol 
• 124-63-0 methanesulfonyl chloride 
• 4252-78-2 2,2',4'-trichloroacetophenone 

Downstream Products

• 85473-17-2 2-(2,4-dichlorophenyl)-1-(1-imidazolyl)-octan-2-ol 
• 78202-32-1 2-(2,4-Dichloro-phenyl)-1-imidazol-1-yl-nonan-2-ol 
• 78220-17-4 1-Cyclopropyl-2-(2,4-dichloro-phenyl)-3-imidazol-1-yl-propan-2-ol 
• 78202-17-2 2-(2,4-dichlorophenyl)-1-(1-imidazolyl)-pentan-2-ol 
• 70827-17-7 1-[2-hydroxy-2-(2,4-dichlorophenyl)hexyl]imidazole 
• 78202-30-9 2-(2,4-Dichloro-phenyl)-1-imidazol-1-yl-hept-6-en-2-ol 
• 78202-29-6 2-(2,4-Dichloro-phenyl)-1-imidazol-1-yl-4-methyl-pentan-2-ol 
• 488712-23-8 C₁₉H₁₆Cl₂N₂O₃ 
• 83338-21-0 2-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-1,2-propanediol 

Relevant articles and documents

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.

Novel azole or triazole derivatives, method for preparing the same and use thereof as antifungal medicaments

The invention concerns novel azole or triazole derivatives of formula (I), wherein: X, Ar1, Ar3, A, R1, R5, R6, R7 and B are such as defined in the description, their preparation method and their use as antifungal medicines.

Quantitative structure-activity relationships in a group of imidazole antimycotic agents

Quantitative structure-activity relationships (QSAR) have been derived for 2-(2,4-dichlorophenyl)-2-hydroxy-1-(1-imidazolyl)alkanes having antifungal activity against species of Candida, Aspergillus, and dermatophytes. An ideal lipophilicity (logP(o)) has