252964-68-4

Basic information

• Product Name: 2,4-Dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one
• Synonyms: 3H-1,2,4-TRIAZOL-3-ONE, 2,4-DIHYDRO-4-[4-[4-(4-METHOXYPHENYL)-1-PIPERAZINYL]PHENYL]-2-(1-METHYLPROPYL)-;2-SEC-BUTYL-4-(4-[4-(4-METHYLOXY-PHENYL)-PIPERAZIN-1-YL]-PHENYL)-2,4-DIHYDRO-[1,2,4]-TRIAZOL-3-ONE;2-Butan-2-yl-4-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-1,2,4-triazol-3-one;1-SEC BUTYL-[4[4(4-METHOXYPHENYL)-1-PIPERAZINYL]-PHENYL]-1,2,4-TRIAZOLO-5-ONE;2,4-Dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one;2,4-Dihydro-4-[[4-hydroxyphenyl]-1-piperazinyl];2,4-DIHYDRO-4-[[4-HYDROXYPHENYL]-1-PIPERAZINYL] 98.50+% LIGHT GRAY POWDER;3H-1,2,4-Triazol-3-one,2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-
• CAS NO: 252964-68-4
• Molecular Formula: C₂₃H₂₉N₅O₂
• Molecular Weight: 407.51
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 252964-68-4.mol

Chemical Properties

• Melting Point: 189-191 °C
• Boiling Point: 572.4 °C at 760 mmHg
• Flash Point: 300 °C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 4.12E-13mmHg at 25°C
• Refractive Index: 1.622
• PKA: 6.57±0.40(Predicted)
• CAS DataBase Reference: 2,4-Dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one(252964-68-4)
• EPA Substance Registry System: 2,4-Dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one(252964-68-4)

Safety Data

• Hazardous Substances Data: 252964-68-4(Hazardous Substances Data)

Usage

Uses

An intermediate of Itraconazole.

InChI:InChI=1/C23H29N5O2/c1-4-18(2)28-23(29)27(17-24-28)21-7-5-19(6-8-21)25-13-15-26(16-14-25)20-9-11-22(30-3)12-10-20/h5-12,17-18H,4,13-16H2,1-3H3

Upstream product

• 939027-86-8 N'-sec-butylformohydrazide 
• 74853-06-8 phenyl (4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate 
• 74852-61-2 1-(4-methoxyphenyl)-4-(4-nitrophenyl)-piperazine 
• 100-00-5 4-chlorobenzonitrile 
• 38212-30-5 4-(4-methoxyphenyl)piperazine 
• 78-76-2 s-butyl bromide 
• 74853-07-9 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one 
• 59541-76-3 butan-2-one formylhydrazone 
• 74852-62-3 4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenylamine 

Downstream Products

• 106461-41-0 (-)-(R)-2,4dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol 3-one 
• 252964-65-1 (2S,4R)-itraconazole 
• 84604-65-9 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.

ITRACONAZOLE ANALOGUES AND METHODS OF USE THEREOF

Disclosed herein are analogues of itraconazole that are both angiogenesis and hedgehog signaling pathway inhibitors. The compounds are expected to be useful in the treatment of cancer, particularly cancers that are dependent upon the hedgehog signaling pathway such as basal cell carcinoma and medulloblastoma.

SMALL MOLECULE INHIBITORS OF FIBROSIS

Described herein are compounds and compositions for the treatment of a fibrotic disease.

CHIRALLY PURE ISOMERS OF ITRACONAZOLE AND INHIBITORS OF LANOSTEROL 14A- DEMETHYLASE FOR USE AS ANGIOGENESIS INHIBITORS

Described herein are methods of inhibiting angiogenesis, and treating or preventing a disease or disorder (or symptoms thereof) associated with angiogenesis, wherein an anti-angiogenesis compound is administered to a subject.