486-38-4

Usage

Chemical structure

1,2-Dihydro-1,2-dimethyl-5-phenyl-3H-pyrazol-3-one

Class

Pyrazolone derivatives

Appearance

Unknown, but likely a solid due to its molecular weight and structure

Solubility

Unknown, but likely soluble in organic solvents such as ethanol or methanol

Pharmacological properties

Antidepressant activity due to inhibition of serotonin reuptake

Discontinued

Yes, due to concerns about causing Guillain-Barré syndrome

Current status

Primarily of interest to researchers studying chemical structures and pharmacological properties of pyrazolone derivatives

Potential applications

Research and development in the field of medicinal chemistry and drug discovery

Safety concerns

Guillain-Barré syndrome risk

Mechanism of action

Inhibition of serotonin reuptake in the brain, leading to increased levels of serotonin and improved mood regulation

Chemical properties

Unknown, but likely stable under normal conditions due to its structure

Synthesis

Unknown, but likely synthesized through chemical reactions involving pyrazolone and phenyl groups

Structural features

Pyrazolone ring, phenyl group, and two methyl groups attached to the 1,2-positions of the pyrazolone ring

Upstream product

• 27412-71-1 5-phenyl-1H-pyrazol-3(2H)-one 
• 74-88-4 methyl iodide 
• 540-73-8 1,2-Dimethylhydrazine 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 13466-32-5 acetophenone dimethylhydrazone 
• 306-37-6 N,N'-Dimethylhydrazine dihydrochloride 
• 98-88-4 benzoyl chloride 
• 14331-27-2 1-acetyl-2-benzoylhydrazine 
• 610289-29-7 1,1-dimethylamino-5-phenylpyrrole-2,3-dione 
• 138211-83-3 N'-acetyl-N,N'-dimethylbenzohydrazide 

Downstream Products

• 104996-64-7 1,2-dimethyl-3-oxo-5-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde 

Relevant academic research and scientific papers

HETEROCYCLIC COMPOUND AS PROTEIN KINASE INHIBITOR

Provided are novel heterocyclic compounds useful as anti-cancer drugs by suppressing protein kinase activities of growth factor receptors such as c-Met, pharmaceutical compositions containing the same, and methods for using the compound.

N-Aminopyrroledione-hydrazonoketene-pyrazolium oxide-pyrazolone rearrangements and pyrazolone tautomerism

Flash vacuum thermolysis (FVT) of 1-(dimethylamino)pyrrole-2,3-diones 5 causes extrusion of CO with formation of transient hydrazonoketenes 7. The transient ketenes 7 are observable in the form of weak bands at 2130 (7a) or 2115 cm-1 (7b) in the Ar matrix IR spectra resulting from either FVT or photolysis of either 5 or 1,1-dimethylpyrazolium-5-oxides 8, and these absorptions are in excellent agreement with B3LYP/6-31G* frequency calculations. Under FVT conditions the ketenes 7 cyclize to pyrazolium oxides 8, which undergo 1,4-migration of a methyl group to yield 1,4-dimethyl-3-phenylpyrazole-5(4H)-one 9a and 1,4,4-trimethyl-3-phenylpyrazole-5(4H)-one 9b. All three tautomers of 9a have been characterized, viz. the CH form 9a (most stable form in the gas phase, the solid state and solvents of low polarity), the OH form 9a′ (metastable solid at room temperature) and the NH form 9a″ (stable in aprotic dipolar solvents). The isomeric 1,4-dimethyl-5-phenylpyrazole-3(2H)-one 12 tautomerizes to the 3-hydroxypyrazole 12′. The crystal structure of the hydrochloride 14 of 9a′/9a″ is reported, representing the first structurally characterised example of a protonated 5-hydroxypyrazole.

A new method for synthesis of 1H-pyrazol-3(2H)-ones

A new preparative method is reported for the synthesis of 4,5-disubstituted 1,2-dimethyl-1H-pyrazol-3(2H)-ones 5a-e,g-k from N,N-diacyl-N,N'-dimethylhydrazines 1a-e,g,h,j,k. The method is based on the intramolecular formation of thc 4,5-bond in the pyrazo

Mechanisms of Heterocycle Ring Formation. Part 5. A Carbon-13 Nuclear Magnetic Resonance Study of Pyrazolinone Synthesis by the Reaction of β-Ketoesters with Substituted Hydrazines

The 16 reactions between each of four hydrazines and four β-ketoesters have been followed by 13C n.m.r. spectroscopy.Peaks were assigned to starting materials, intermediates, and products, and reaction mechanisms determined and rationalized.Most rections proceed by attack of the least hindered hydrazine nitrogen atom on the keto carbon group of the ketoester.Relative rates of nucleophilic attack determine the build-up of intermediate and in some cases the nature of the products formed.