154003-18-6

Basic information

• Product Name: 3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl )-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[ (1S)-1-methylpropyl]-
• CAS NO: 154003-18-6
• Molecular Formula: C35H38Cl2N8O4
• Molecular Weight: 705.644
• Mol File: 154003-18-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl )-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[ (1S)-1-methylpropyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl )-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[ (1S)-1-methylpropyl]-(154003-18-6)
• EPA Substance Registry System: 3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl )-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[ (1S)-1-methylpropyl]-(154003-18-6)

Safety Data

• Hazardous Substances Data: 154003-18-6(Hazardous Substances Data)

Upstream product

• 125235-31-6 (S)-2-(sec-butyl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 154003-23-3 (2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-4-tozyloxymethyl-1,3-dioxolane 
• 84604-65-9 itraconazole 
• 172587-56-3 Benzoic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester 
• 172587-57-4 (2R,4S)-(+)-2-(2,4-dichlorophenyl)-2-<(1H-1,2,4-triazol-1-yl)methyl>-1,3-dioxolane-4-methanol 
• 58905-16-1 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone 

Relevant articles and documents

An optical pure itraconazole key intermediate and synthetic method and by the intermediate synthesis of optically pure itraconazole method

The invention disclsoes an optically pure itraconazole key intermediate and synthetic method thereof, and a method for synthesizing the optically pure itraconazole from the intermediate. The method of the invention uses 1-(2,4-dichlorobenzene)-2-(1-methylene-1,2,4-triazole)-1-ketone for preparing the optically pure itraconazole key intermediate, and the optically pure itraconazole key intermediate is used for the preparation of optically pure itraconazole. The method uses easily available raw materials, not only reduces the production cost, but also obtains the product with high purity; through the control of the optical purity of the key intermediate compound VII, the optical purity of the target product itraconazole can be effectively controlled; therefore, the invention has with industrial value.

Impact of absolute stereochemistry on the antiangiogenic and antifungal activities of itraconazole

Itraconazole is used clinically as an antifungal agent and has recently been shown to possess antiangiogenic acitivity. Itraconazole has three chiral centers that give rise to eight stereoisomers. The complete role of stereochemistry in the two activities of itraconazole, however, has not been addressed adequately. For the first time, all eight stereoisomers of itraconazole (1a?h) have been synthesized and evaluated for activity against human endothelial cell proliferation and for antifungal activity against five fungal strains. Distinct antiangiogenic and antifungal activity profiles of the trans stereoisomers, especially 1e and 1f, suggest different molecular mechanisms underlying the antiangiogenic and antifungal activities of itraconazole.