946-23-6

Usage

Chemical class

Pyrazolines.

Physical appearance

Yellow crystalline solid.

Common use

Spin trapping agent in electron paramagnetic resonance (EPR) spectroscopy.

Purpose

To detect and characterize free radicals and reactive oxygen species.

Structural feature

Stable nitroxide radical.

Area of interest

Studying biological and chemical systems with generation and reactivity of free radicals.

Potential properties

Antioxidant and anti-inflammatory.

Field of significance

Free radical research.

InChI:InChI=1/C11H12N2O/c1-9-7-11(14)13(12-9)8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 555-96-4 Benzylhydrazine 
• 20570-96-1 benzylhydrazine dihydrochloride 
• 1073-62-7 N-benzylhydrazine hydrochloride 

Downstream Products

• 137513-69-0 2-Benzyl-5-methyl-4-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-2,4-dihydro-pyrazol-3-one 
• 137513-71-4 C₂₉H₂₇N₅O₄ 
• 137513-72-5 C₂₉H₂₇N₅O₄ 
• 89936-51-6 2-Benzyl-5-methyl-4-[1-phenyl-meth-(Z)-ylidene]-2,4-dihydro-pyrazol-3-one 
• 89936-59-4 C₂₉H₂₈N₄O₂ 
• 89936-62-9 C₂₉H₂₈N₄O₂ 
• 89936-49-2 4-(p-Methoxybenzylidene)-1-benzyl-3-methylpyrazolin-5-one 
• 89936-57-2 4,4'-(p-Methoxybenzylidene)bis(1-benzyl-3-methylpyrazolin-5-one) 
• 89936-60-7 4,4'-(p-Methoxybenzylidene)bis(1-benzyl-3-methylpyrazolin-5-one) enolic form 
• 619307-80-1 1-(1-benzyl-5-hydroxy-3-methyl-1H-pyrazol-4-yl)(phenyl)methanone 
• 619307-79-8 1-(1-benzyl-5-hydroxy-3-methyl-1H-pyrazol-4-yl)ethanone 
• 85184-64-1 1-benzyl-3-methylpyrazolo[4',3':5,6]pyrano[2,3-b]pyridin-4(1H)-one 
• 1240508-57-9 (1-benzyl-5-hydroxy-3-methyl-1H-pyrazol-4-yl)(5-chloro-1-phenyl-1H-pyrazol-4-yl)methanone 
• 1440199-91-6 1-benzyl-4-fluoro-3-methyl-4-(2-nitro-1-phenylethyl)-1H-pyrazol-5(4H)-one 

Relevant academic research and scientific papers

Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones

The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.

Metal-Free Direct C–H Thiolation and Thiocyanation of Pyrazolones

Metal-free approach for direct C–H thiolation and thiocyanation of N-substituted pyrazolones with disulfides and thiocyanate salts, respectively, are developed. These reactions allow the C–S bond coupling to proceed effectively under mild conditions, providing useful and convenient methods for preparation of a series of 4-thio-substituted pyrazolone analogues, which have potential applications in organic, medicinal and material chemistry. Preliminary mechanistic investigation suggested that radical processes are likely to involve in these transformations.

P-Toluenesulphonic acid-promoted, I2-catalysed sulphenylation of pyrazolones with aryl sulphonyl hydrazides

Aryl pyrazolone thioethers were synthesized via the I2-catalysed cross-coupling of pyrazolones with aryl sulphonyl hydrazides in the presence of p-toluenesulphonic acid, which has been proposed to promote the reaction by facilitating the decomposition of sulphonyl hydrazides. This journal is

DRUGS COMPRISING COMBINATION OF ANTITHROMBOTIC AGENT WITH PYRAZOLONE DERIVATIVE

It is intended to provide drugs for treating and/or preventing ischemic diseases which are safe and have little side effects. Namely, drugs comprising a combination of an antithrombotic agent and a pyrazolone derivative defined in the description or its pharmaceutically acceptable salt.

Thrombopoietin mimetics

Non-peptide TPO mimetics are disclosed, as well as a method of treating thrombocytopenia, in a mammal, including a human, in need thereof, which comprises administering to such mammal an effective amount of a selected hydroxy-1-azo-naphthalene derivative.

Hydrazinonaphthalene and azonaphthalene thrombopoietin mimics are nonpeptidyl promoters of megakaryocytopoiesis

High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW 50 values in the region of 1-20 nM.

SYNTHESIS OF 1,3-DISUBSTITUTED 4-HYDROXYIMINO-5-PYRAZOLONES FROM N-ALKYL(ARYLALKYL)-N-NITROSOHYDRAZINES

The reaction of N-propyl- and N-benzyl-N-nitrosohydrazines with acetoacetic ester leads to the formation of 1-propyl- and 1-benzyl-3-methyl-4-hydroxyimino-5-pyrazolones.