1224885-01-1

Basic information

• Product Name: C₂₀H₁₉Cl₂N₃O₅S
• Synonyms: C₂₀H₁₉Cl₂N₃O₅S
• CAS NO: 1224885-01-1
• Molecular Weight: 484.36
• Mol File: 1224885-01-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₂₀H₁₉Cl₂N₃O₅S(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₀H₁₉Cl₂N₃O₅S(1224885-01-1)
• EPA Substance Registry System: C₂₀H₁₉Cl₂N₃O₅S(1224885-01-1)

Safety Data

• Hazardous Substances Data: 1224885-01-1(Hazardous Substances Data)

Upstream product

• 2631-72-3 2,4-dichlorophenacyl bromide 
• 23735-43-5 (S)-1-O-tosyl-2,3-O-isopropylideneglycerol 
• 98-59-9 p-toluenesulfonyl chloride 
• 50765-70-3 (S)-1-tosyloxy-2,3-propanediol 
• 58905-16-1 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone 

Downstream Products

• 848585-69-3 (2R,4R,2'S)-Itraconazole 
• 848585-68-2 (2R,4R,2'R)-Itraconazole 

Relevant articles and documents

Design and Synthesis of Tetrazole- And Pyridine-Containing Itraconazole Analogs as Potent Angiogenesis Inhibitors

Itraconazole, a widely used antifungal drug, was found to possess antiangiogenic activity and is currently undergoing multiple clinical trials for the treatment of different types of cancer. However, it suffers from extremely low solubility and strong interactions with many drugs through inhibition of CYP3A4, limiting its potential as a new antiangiogenic and anticancer drug. To address these issues, a series of analogs in which the phenyl group is replaced with pyridine or fluorine-substituted benzene was synthesized. Among them the pyridine- and tetrazole-containing compound 24 has significantly improved solubility and reduced CYP3A4 inhibition compared to itraconazole. Similar to itraconazole, compound 24 inhibited the AMPK/mTOR signaling axis and the glycosylation of VEGFR2. It also induced cholesterol accumulation in the endolysosome and demonstrated binding to the sterol-sensing domain of NPC1 in a simulation study. These results suggested that compound 24 may serve as an attractive candidate for the development of a new generation of antiangiogenic drug.

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.