125235-74-7

Basic information

• Product Name: 2-[(2R)-butan-2-yl]-4-{4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one
• Synonyms: 2-[(2R)-Butan-2-yl]-4-{4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one; 3H-1,2,4-triazol-3-one, 2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-[(1R)-1-methylpropyl]-
• CAS NO: 125235-74-7
• Molecular Formula: C₂₂H₂₇N₅O₂
• Molecular Weight: 393.4821
• Mol File: 125235-74-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 587.9°C at 760 mmHg
• Flash Point: 309.4°C
• Density: 1.25g/cm³
• Vapor Pressure: 2.03E-14mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: 2-[(2R)-butan-2-yl]-4-{4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(2R)-butan-2-yl]-4-{4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one(125235-74-7)
• EPA Substance Registry System: 2-[(2R)-butan-2-yl]-4-{4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one(125235-74-7)

Safety Data

• Hazardous Substances Data: 125235-74-7(Hazardous Substances Data)

Upstream product

• 149809-44-9 (R)-2-(sec-butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 

Downstream Products

• 848585-70-6 (2S,4S,2'R)-Itraconazole 
• 154003-19-7 (2S,4R,2'S)-Itraconazole 
• 154003-17-5 (2R,4S,2'S)-Itraconazole 
• 848585-68-2 (2R,4R,2'R)-Itraconazole 

Relevant articles and documents

Repurposing the Clinically Efficacious Antifungal Agent Itraconazole as an Anticancer Chemotherapeutic

Itraconazole (ITZ) is an FDA-approved member of the triazole class of antifungal agents. Two recent drug repurposing screens identified ITZ as a promising anticancer chemotherapeutic that inhibits both the angiogenesis and hedgehog (Hh) signaling pathways. We have synthesized and evaluated first- and second-generation ITZ analogues for their anti-Hh and antiangiogenic activities to probe more fully the structural requirements for these anticancer properties. Our overall results suggest that the triazole functionality is required for ITZ-mediated inhibition of angiogenesis but that it is not essential for inhibition of Hh signaling. The synthesis and evaluation of stereochemically defined des-triazole ITZ analogues also provides key information as to the optimal configuration around the dioxolane ring of the ITZ scaffold. Finally, the results from our studies suggest that two distinct cellular mechanisms of action govern the anticancer properties of the ITZ scaffold.

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.