112559-81-6

Basic information

• Product Name: 4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol
• Synonyms: 1-(4-HYDROXYPHENYL)-4-(4-NITROPHENYL)-PIPERAZINE;4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol;4-(4-(4-nitrophenyl)piperazin-1-yl)phenol;4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenol;4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol Itraconazole interMediate
• CAS NO: 112559-81-6
• Molecular Formula: C₁₆H₁₇N₃O₃
• Molecular Weight: 299.32
• EINECS: 601-189-8
• Product Categories: Heterocyclic Compounds
• Mol File: 112559-81-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 540.833 °C at 760 mmHg
• Flash Point: 280.886 °C
• Appearance: white like or light brown crystalline powder
• Density: 1.317 g/cm³
• Vapor Pressure: 2.61E-12mmHg at 25°C
• Refractive Index: 1.65
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly, Heated)
• PKA: 12.18±0.30(Predicted)
• CAS DataBase Reference: 4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol(112559-81-6)
• EPA Substance Registry System: 4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol(112559-81-6)

Safety Data

• Hazardous Substances Data: 112559-81-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 112559-81-6 differently. You can refer to the following data:
1. 4-[4-(4-Nitrophenyl)-1-piperazinyl]phenol is a key intermediate in the synthesis of triazole medicines, used in curing deep department fungal infections. Inhibitor of endothelial cell proliferation.
2. 4-[4-(4-Nitrophenyl)-1-piperazinyl]phenol is a key intermediate in the synthesis of triazole medicines, such as itraconazole (I937500), which are used in curing deep department fungal infections. Inhibitor of endothelial cell proliferation.

InChI:InChI=1/C16H17N3O3/c20-16-7-5-14(6-8-16)18-11-9-17(10-12-18)13-1-3-15(4-2-13)19(21)22/h1-8,20H,9-12H2

Upstream product

• 153466-15-0 4-[4-(4-nitro-phenyl)-piperazin-1-yl]-phenylamine 
• 38212-30-5 4-(4-methoxyphenyl)piperazine 
• 67455-41-8 4-(piperazin-1-yl)aniline 
• 56621-48-8 1-(4-hydroxyphenyl)piperazine 
• 100-00-5 4-chlorobenzonitrile 
• 84145-43-7 1-(para-methoxyphenyl)piperazine hydrochloride 
• 104-94-9 4-methoxy-aniline 
• 350-46-9 4-Fluoronitrobenzene 
• 6269-89-2 1-(4-Nitrophenyl)piperazine 
• 100-25-4 para-dinitrobenzene 
• 586-78-7 para-nitrophenyl bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 74852-61-2 1-(4-methoxyphenyl)-4-(4-nitrophenyl)-piperazine 
• 123-30-8 4-amino-phenol 

Downstream Products

• 1246815-17-7 4-(4-(4-(methoxymethoxy)phenyl)piperazin-1-yl)aniline 
• 1339803-88-1 C₁₉H₂₅N₅O₃ 
• 1329503-19-6 C₂₅H₂₇N₃O₄ 

Relevant articles and documents

Structure-Activity Relationships for Itraconazole-Based Triazolone Analogues as Hedgehog Pathway Inhibitors

The Food and Drug Administration-approved antifungal agent, itraconazole (ITZ), has been increasingly studied for its novel biological properties. In particular, ITZ inhibits the hedgehog (Hh) signaling pathway and has the potential to serve as an anticancer chemotherapeutic against several Hh-dependent malignancies. We have extended our studies on ITZ analogues as Hh pathway inhibitors through the design, synthesis, and evaluation of novel des-triazole ITZ analogues that incorporate modifications to the triazolone/side chain region of the scaffold. Our overall results suggest that the triazolone/side chain region can be replaced with various functionalities (hydrazine carboxamides and meta-substituted amides) resulting in improved potency when compared to ITZ. Our studies also indicate that the stereochemical orientation of the dioxolane ring is important for both potent Hh pathway inhibition and compound stability. Finally, our studies suggest that the ITZ scaffold can be successfully modified in terms of functionality and stereochemistry to further improve its anti-Hh potency and physicochemical properties.

Itraconazole-based Smo inhibitor as well as preparation method and application thereof

The invention discloses an itraconazole-based Smo inhibitoras well as a preparation method and application of the Smo inhibitor. The Smo inhibitor has a structural formula shown as a formula (I). The invention also discloses a preparation method and application of the material. According to the invention, itraconazole is used as a lead compound, optimization and transformation are carried out on the basis of the itraconazole, and the Smo inhibitor with good inhibitory activity is obtained.

ANTI-FUNGAL TREATMENT

Provided are compounds, methods, and pharmaceutical compositions useful for treatment of fungal infections, e.g., aspergillosis, candidiasis, cryptococcosis, histoplasmosis, and the like. For example, the pharmaceutical composition may include a pharmaceutically acceptable carrier or excipient, and a compound represented by Ar— C(=NR1)NR2— A---X— Y— Het2 and pharmaceutically acceptable salts thereof. Ar may be an optionally substituted aryl or nitrogen- containing heteroaryl. R1 and R2 may independently be H, optionally substituted C1-C6 aikyi, or optionally substituted C3-C6 cyeloalkyi. A may be a bond or an optionally substituted linking moiety comprising 1, 2, or 3 rings. Each ring in the optionally substituted linking moiety may independently be one of: aryl, cyeloalkyi, heterocycloalkyl, and heteroaryl. X may be O, S, amide, or a bond. Y may be optionally substituted C1-C10 alkyi or optionally substituted C2-C10 alkenyl. Het2 may be an optionally substituted five-membered nitrogen-containing heteroaromatic ring comprising 1, 2, or 3 ring heteroatoms.