74853-06-8

Basic information

• Product Name: 4-([4-(4-METHYLOXY-PHENYL)-PIPERAZIN-1-YL]-PHENYL)-CARBAMIC ACID PHENYL ESTER
• Synonyms: 4-([4-(4-METHYLOXY-PHENYL)-PIPERAZIN-1-YL]-PHENYL)-CARBAMIC ACID PHENYL ESTER;N-[4[4(4-METHOXYPHENYL)-1-PIPERAZINYL]-PHENYL]PHENYLCARBAMATE;[4-(4-Methoxypiperazine-1-Yl)Phenyl]carbamic Acid Phenyl Ester;[4-[4-(4-Methoxyphenyl)-1-piperazinyl]phenyl]carbaMic Acid Phenyl Ester;4-([4-(4-METHYLOXY-PHENYL)-PIPERAZIN-1-YL]-PHENYL)-CARBAMIC ACID PHENYL ESTER(WXG01572)
• CAS NO: 74853-06-8
• Molecular Formula: C₂₄H₂₅N₃O₃
• Molecular Weight: 403.47
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 74853-06-8.mol

Chemical Properties

• Melting Point: 184-188 °C (decomp)
• Boiling Point: 586.2±50.0 °C(Predicted)
• Appearance: /
• Density: 1.237±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: DMF (Slightly), DMSO (Slightly)
• PKA: 12.79±0.70(Predicted)
• CAS DataBase Reference: 4-([4-(4-METHYLOXY-PHENYL)-PIPERAZIN-1-YL]-PHENYL)-CARBAMIC ACID PHENYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-([4-(4-METHYLOXY-PHENYL)-PIPERAZIN-1-YL]-PHENYL)-CARBAMIC ACID PHENYL ESTER(74853-06-8)
• EPA Substance Registry System: 4-([4-(4-METHYLOXY-PHENYL)-PIPERAZIN-1-YL]-PHENYL)-CARBAMIC ACID PHENYL ESTER(74853-06-8)

Safety Data

• Hazardous Substances Data: 74853-06-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-([4-(4-METHYLOXY-PHENYL)-PIPERAZIN-1-YL]-PHENYL)-CARBAMIC ACID PHENYL ESTER is used as a synthetic intermediate for the development of various chemical compounds. Its unique structure allows it to be a valuable building block in the creation of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-([4-(4-METHYLOXY-PHENYL)-PIPERAZIN-1-YL]-PHENYL)-CARBAMIC ACID PHENYL ESTER is used as a key component in the synthesis of drugs targeting specific biological pathways. Its chemical properties make it suitable for the development of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Chemical Research:
4-([4-(4-METHYLOXY-PHENYL)-PIPERAZIN-1-YL]-PHENYL)-CARBAMIC ACID PHENYL ESTER is also utilized in chemical research as a model compound to study the properties and reactivity of similar structures. This helps researchers gain a deeper understanding of the underlying chemical mechanisms and potentially discover new applications for this class of compounds.

Upstream product

• 38212-30-5 4-(4-methoxyphenyl)piperazine 
• 100-00-5 4-chlorobenzonitrile 
• 108-20-3 di-isopropyl ether 
• 74852-62-3 4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenylamine 
• 1885-14-9 phenyl chloroformate 
• 74852-61-2 1-(4-methoxyphenyl)-4-(4-nitrophenyl)-piperazine 

Downstream Products

• 847951-96-6 1,3-dihydro-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3-(1-methylethyl)-2H-imidazol-2-one 
• 219923-85-0 1-[4-(4-{4-[(2R,4S)-4-(2,4-Difluoro-phenyl)-4-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-2-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-3-isopropyl-imidazolidin-2-one 
• 219923-85-0 (2S-cis)-1-{4-[4-(4-{[4-(2,4-difluorophenyl)-4-(1H-1,2,4-triazol-1-yl-methyl)-1,3-dioxolan-2-yl]methoxy}phenyl)-piperazin-1-yl]phenyl}-3-(1-methylethyl)-2-imidazolidinone 
• 79538-92-4 4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1-methyl-1H-1,2,4-triazol-5(4H)-one 
• 74853-07-9 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one 
• 74852-90-7 2,4-dihydro-4-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}-5-methyl-3H-1,2,4-triazol-3-one 
• 74852-91-8 4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1-methyl-1H-1,2,4-triazol-5(4H)-one 
• 74853-20-6 1-ethyl-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one 
• 79538-91-3 4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-2-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 74852-95-2 1-ethyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one 
• 89848-19-1 4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1-isopropyl-1H-1,2,4-triazol-5(4H)-one 
• 74853-17-1 4-{4-[4-(4-Hydroxy-phenyl)-piperazin-1-yl]-phenyl}-2,5-dimethyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-21-5 4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1-isobutyl-1H-1,2,4-triazol-5(4H)-one 
• 89848-20-4 1-butyl-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-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.

SMALL MOLECULE INHIBITORS OF FIBROSIS

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

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.

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.

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.

Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology

In search for new compounds with potential for clinical use as antifungal agents in dermatology, a series of 12 azole compounds were synthesized stereospecifically and investigated specifically for their activity against dermatophyte fungal infections in

Substituted azolone derivatives

The use for the manufacture of a medicament for treating Helicobacter-related diseases of a compound of formula STR1 a pharmaceutically acceptable acid addition salt or a stereochemically isomeric form thereof, wherein X and Y each independently are CH or N; R1, R2 and R3 each independently are hydrogen or C1-4 alkyl; R4 and R5 each independently are hydrogen, halo, C1-4 alkyl, C1-4 alkyloxy, hydroxy, trifluoromethyl, trifluoromethyloxy or difluoromethyloxy; Z is C=O or CHOH; and Ar is phenyl optionally substituted with up to three substituents selected from hydroxy, C1-4 alkyl, C1-4 alkyloxy, halo, trifluoromethyl, triC1-4 alkylsilyloxy, nitro, amino and cyano or pyridinyl substituted with hydroxy or C1-4 alkyloxy; and --A-- is a radical of formula STR2

[[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles having anti-microbial properties

Novel [[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles, having anti-microbial activity, compositions containing the same, and methods of inhibiting and/or eliminating the development of fungi and

Antimycotic azoles. 7. Synthesis and antifungal properties of a series of novel triazol-3-ones

A series of novel triazol-3-ones has been synthesized, and their in vitro and in vivo antifungal properties are reported. Traconazole. which displays a pronounced oral activity against vaginal candidosis in rats and against microsporosis in guinea pigs, has been selected for clinical evaluation.