34320-83-7

Basic information

• Product Name: 3-(4-NITROPHENYL)-1-PHENYL-2-PYRAZOLIN-5-ONE
• Synonyms: 3-(4-NITROPHENYL)-1-PHENYL-2-PYRAZOLIN-5-ONE;CAY10550;2,4-Dihydro-5-(4-nitrophenyl)-2-phenyl-3H-pyrazol-3-one;TCS PrP Inhibitor 13;3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-5(4H)-one;5-(4-nitrophenyl)-2-phenyl-4H-pyrazol-3-one
• CAS NO: 34320-83-7
• Molecular Formula: C₁₅H₁₁N₃O₃
• Molecular Weight: 281.27
• Mol File: 34320-83-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 465.949°C at 760 mmHg
• Flash Point: 235.598°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: Store at +4°C
• CAS DataBase Reference: 3-(4-NITROPHENYL)-1-PHENYL-2-PYRAZOLIN-5-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-NITROPHENYL)-1-PHENYL-2-PYRAZOLIN-5-ONE(34320-83-7)
• EPA Substance Registry System: 3-(4-NITROPHENYL)-1-PHENYL-2-PYRAZOLIN-5-ONE(34320-83-7)

Safety Data

• Hazardous Substances Data: 34320-83-7(Hazardous Substances Data)

Usage

Uses

TCS PrP Inhibitor 13 is a PrP-res accumulation inhibitor.

Biological Activity

Antiprion agent. Potently inhibits protease-resistant prion protein (PrP-res) accumulation in two types of prion-infected mouse neuroblastoma (N2a) cell lines (IC 50 = 3 nM).

InChI:InChI=1/C15H11N3O3/c19-15-10-14(11-6-8-13(9-7-11)18(20)21)16-17(15)12-4-2-1-3-5-12/h1-10,16H

Upstream product

• 89-25-8 edaravone 
• 61466-08-8 5,5'-bis-(4-nitro-phenyl)-2,2'-diphenyl-1,2,2',4'-tetrahydro-4,4'-methanylylidene-bis-pyrazol-3-one 
• 838-57-3 ethyl 4-nitrobenzoylacetate 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 

Downstream Products

• 77169-06-3 4,4-Dibromo-5-(4-nitro-phenyl)-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 59439-99-5 1-phenyl-3-(p-nitrophenyl)-4-(p-nitrophenylidene)pyrazol-5-one 
• 108-19-0 BIURET 
• 77169-09-6 4,4-Diazido-5-(4-nitro-phenyl)-2-phenyl-2,4-dihydro-pyrazol-3-one 

Relevant articles and documents

Synthesis and cytotoxic evaluation of some substituted 5-pyrazolones and their urea derivatives

In this paper, a series of new substituted-5-pyrazolones were first synthesized, then formulated by the Vilsmeier–Haack reaction to obtain substituted-4-carbaldehyde-5-pyrazolones. In the final step, when urea was reacted with formulated pyrazolones, we found that, instead of the C=N bond in azomethine form, the compounds tautomerized to form a series of novel pyrazole-4ylidenemethylurea structures. The structures of these compounds were elucidated by FTIR, 1H, 13C NMR, LC-MS/MS, and elemental analysis methods. The cytotoxic and antioxidant effects of substituted 5-pyrazolones and their pyrazolone-urea derivatives were investigated in metastatic A431 and noncancerous HaCaT human keratinocytes by a mitochondrial activity test. The effects of the compounds on the migration of cancerous and noncancerous cell lines were investigated by using a cell scratch assay. The General Linear Model, Statistical Package for Social Sciences (SPSS v26) was used to determine if there was a statistically significant difference between the control and the treatment groups. Four of the nine compounds showed an antioxidant effect. All 5-pyrazolone-urea compounds showed higher toxicity (p 0.05) in cancerous A431 cells compared to noncancerous cells at all time points. All compounds also showed a biphasic hormetic effect. Four of the nine compounds inhibited cell migration.

New series of antiprion compounds: Pyrazolone derivatives have the potent activity of inhibiting protease-resistant prion protein accumulation

To find effective antiprion compounds, we synthesized and evaluated various pyrazolone derivatives. Seven of 19 compounds showed inhibition of PrP-res accumulation and the remarkably active compound 13 showed an IC50 value of 3 nM in both ScN2a and F3 cell lines. Findings from studies on physicochemical and biochemical properties suggest that the action mechanism of these compounds does not correlate with any antioxidant activities, any of hydroxyl radical scavenging activities, or any SOD-like activities.

Azines and their acyclic derivatives as transferers of one-carbon fragment in reactions with pyrazolones

Enehydrazine derivatives have been obtained by the reaction of 6-phenyl-1,2,4-triazine 4-oxide with pyrazolones 2, which on further heating with pyrazolones 2 are converted into the corresponding symmetrical or unsymmetrical derivatives of dipyrazolylmethane. Enehydrazine derivatives of 1,3-dimethyl-5-nitrosouracil and 1,3-dimethylimidazolidine interact with 3-methyl-1-phenyl-5-pyrazolone (2a) with the formation of dipyrazolylmethane derivative. On interacting compound 2a or 3-methyl-1-(p-nitrophenyl)-5-pyrazolone with 3,6-diphenyl-1,2,4-triazine 4-oxide 12 the corresponding 4,4′-bispyrazolones are formed, but the interaction of compound 12 with 3-(p-nitrophenyl)-1-phenyl-5-pyrazolone leads to dipyrazolylmethane derivative. Dipyrazolylmethane derivative is obtained on heating of fervenulin 4-oxide, 2,4-dihydroxy-5-nitropyrimidine, and 1,3,5-triazines: 6-azauracil, 5-azauracil, azacytosine, and 2,4-diamino-s-triazine with pyrazolone 2a.