149809-44-9

Basic information

• Product Name: 3H-1,2,4-TRIAZOL-3-ONE, 2,4-DIHYDRO-4-[4-[4-(4-METHOXYPHENYL)-1-PIPERAZINYL]PHENYL]-2-(1-METHYLPROPYL)-, (R)-
• Synonyms: 3H-1,2,4-TRIAZOL-3-ONE, 2,4-DIHYDRO-4-[4-[4-(4-METHOXYPHENYL)-1-PIPERAZINYL]PHENYL]-2-(1-METHYLPROPYL)-, (R)-
• CAS NO: 149809-44-9
• Molecular Formula: C₂₃H₂₉N₅O₂
• Molecular Weight: 407.51
• Mol File: 149809-44-9.mol

Chemical Properties

• 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: 3H-1,2,4-TRIAZOL-3-ONE, 2,4-DIHYDRO-4-[4-[4-(4-METHOXYPHENYL)-1-PIPERAZINYL]PHENYL]-2-(1-METHYLPROPYL)-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-1,2,4-TRIAZOL-3-ONE, 2,4-DIHYDRO-4-[4-[4-(4-METHOXYPHENYL)-1-PIPERAZINYL]PHENYL]-2-(1-METHYLPROPYL)-, (R)-(149809-44-9)
• EPA Substance Registry System: 3H-1,2,4-TRIAZOL-3-ONE, 2,4-DIHYDRO-4-[4-[4-(4-METHOXYPHENYL)-1-PIPERAZINYL]PHENYL]-2-(1-METHYLPROPYL)-, (R)-(149809-44-9)

Safety Data

• Hazardous Substances Data: 149809-44-9(Hazardous Substances Data)

Usage

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/t18-/m1/s1

Upstream product

• 50896-54-3 (S)-(+)-1-methylpropyl p-toluenesulfonate 
• 74853-07-9 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one 
• 91799-57-4 (S)-sec-butyl 4-bromobenzenesulfonate 

Downstream Products

• 125235-74-7 (R)-2-(sec-butyl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 

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.

Tri-substituted tetrahydrofuran antifungals

An antifungal compound represented by formula [I]: wherein X is independently both F or both Cl or one X is F and the other is Cl; Y=R'= (C1-C10) alkyl; (C2-C10)alkenyl; (C2-C10)alkynyl; (C3-C8)cycloalky or CH2R2; R2= (C1-C3)perhaloalkyl; CO2R3 *CH(OR4)CH2OR4 or CH2N(R5) R3= lower alkyl or H R4= R3 or (CH2)2OR3 R5= lower alkyl Z=H, or (C1-C5) alkanoyl and the carbons with the asterisks (*) have the R or S absolute configuration; or a pharmaceutically acceptable salt thereof as well as pharmacetical compositions containing them and a methods of treating or preventing fungal infections in mammals using them are disclosed.