142128-66-3

Basic information

• Product Name: (2R,4R)-trans-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane
• Synonyms: (2R,4R)-trans-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane
• CAS NO: 142128-66-3
• Molecular Weight: 544.273
• Mol File: 142128-66-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,4R)-trans-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-trans-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane(142128-66-3)
• EPA Substance Registry System: (2R,4R)-trans-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane(142128-66-3)

Safety Data

• Hazardous Substances Data: 142128-66-3(Hazardous Substances Data)

Upstream product

• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 2631-72-3 2,4-dichlorophenacyl bromide 
• 82966-35-6 (2R,4S)-trans-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-1,3-dioxolane 
• 67914-60-7 N-acetyl-N'-(4-hydroxyphenyl)piperazine 

Downstream Products

• 142128-58-3 (2R,4R)-Ketoconazole 

Relevant articles and documents

Stereoisomers of ketoconazole: Preparation and biological activity

The four stereoisomers of the antifungal agent ketoconazole (1) were prepared and evaluated for their selectivity in inhibiting a number of cytochrome P-450 enzymes. Large differences in selectivity among the isomers were observed for inhibition of the cytochromes P-450 involved in steroid biosynthesis, whereas little differences was observed for inhibition of those associated with hepatic drug metabolism. The cis-(2S,4R) isomer 2 was the most effective against rat lanosterol 14α-demethylase, (2S,4R)-2 > (2R,4S)-4 >> (2R,4R)-3 = (2S,4S)-5, and progesterone 17α,20-lyase, (2S,4R)-2 >> (2S,4S)-5 > (2R,4R)-3 = (2R,4S)-4, whereas the cis-(2R,4S) isomer 4 was more effective against cholesterol 7α-hydroxylase, (2R,4S)-4 > (2S,4S)-5 > (2R,4R)-3 > (2S,4R)-2, and the trans-(2S,4S) isomer 5 was the most effective against aromatase, (2S,4R)-5 >> (2R,4R)-3 = (2R,4S)-4 > (2S,4R)-2. The cis- (2S,4R) and trans-(2R,4R) isomers 2 and 3 are equipotent in inhibiting corticoid 11β-hydroxylase and much more effective than their antipodes. Little selectivity was observed for inhibition of cholesterol side chain cleavage or xenobiotic hydroxylases. These data indicate that the affinity of azoles for cytochrome P-450 enzymes involved in steroid synthesis is highly dependent on the stereochemistry of the entire molecule, whereas binding to drug metabolizing enzymes is a less selective process.