54679-59-3

Usage

Chemical structure

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

Natural source

Derived from the Chinese herb Dichroa febrifuga

Traditional use

Treating fevers and malaria

Potential pharmaceutical applications

Anti-malarial and anti-tumor properties

Mechanism of action

Inhibits the proliferation of malaria parasites and cancer cells

Current status

Under investigation for development as a new drug for malaria and cancer treatment

Further research needed

To fully understand the mechanisms of action and potential therapeutic uses of the compound

Upstream product

• 53256-19-2 ethyl (Z)-3-amino-3-phenylacrylate 
• 60-34-4 methylhydrazine 
• 27412-71-1 5-phenyl-1H-pyrazol-3(2H)-one 
• 80-48-8 methyl p-toluene sulfonate 
• 67000-45-7 2,3-dihydro-6-phenylpyrazolo[3,2-b]oxazole 
• 78999-97-0 2-Benzyl-1-methyl-5-phenyl-1,2-dihydro-pyrazol-3-one 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 212247-76-2 2-(2-hydroxyethyl)-5-phenyl-1-tosylpyrazole-3-one 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 212247-89-7 2-(2-cyanoethyl)-1-methyl-5-phenylpyrazol-3-one 
• 212247-91-1 1-methyl-5-phenyl-2-vinylpyrazol-3-one 

Downstream Products

• 112639-78-8 3-Methyl 5-(6-(1-methyl-5-phenylpyrazol-3-yloxy)hexyl) 4-(3-chloro-6-fluoro-2-(trifluoromethyl)phenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate 

Relevant academic research and scientific papers

Consecutive Three-Component Coupling-Addition Synthesis of β-Amino Enoates and 3-Hydroxypyrazoles via Ethyl 3-Arylpropiolates

Two consecutive three-component syntheses furnishing β-amino enoates or 3-hydroxypyrazoles based upon the Sonogashira alkynylation of aryl iodides and ethyl propiolate were established in mostly excellent yields. The ethyl 3-arylpropiolate intermediates are Michael systems which are suited for concatenation with conjugate addition or cyclocondensation giving access to libraries of 21 different β-amino enoates and 17 different 3-hydroxypyrazoles. The rotational barrier of β-pyrrolidino enoates was assessed by studying the coalescence of pyrrolidinyl protons in VT-NMR spectra of electronically different substituted derivatives showing that the electronic substituent effect on the aryl group does not affect the height of the rotational barrier. This indicates that the substituents are essentially oriented orthogonally to the plane of the β-pyrrolidino enoates.

Unambiguous synthesis of 1-methyl-3-hydroxypyrazoles

2,3-Dihydropyrazolo[3,2-b]oxazoles were used as intermediates in a new method for preparation of N1-methyl-3-hydroxypyrazoles. Synthesis of this bicyclic system was achieved either by alkylation of 3-hydroxypyrazole with 1,2-dibromoethane or, with better

Reactivity of p-Phenyl Substituted β-Enamino Compounds using K-10/ultrasound. I. Synthesis of Pyrazoles and Pyrazolinones

The reactivity of the β-enamino ketones, 3-amino-l-(p-phenyl-substituted)-2-buten-l-ones la-d and β-enamino esters. Ethyl-3-amino-3-(p-phenyl-substituted)-2-propenoates 5a-d were evaluated by systematic studies of the reactions with hydrazine and methylhydrazine by reactions with solid support K-10/ultrasound and homogeneous media (reflux in ethanol or dichloromethane) yielding pyrazole rings 2a-d, Af-methylpyrazoles 3a-d, 4a-d and N-methylpyrazolinones 6a-c and 7a-c. The regiochemistry of the cyclization showed dependence of the reaction conditions employed as well as the substituent in the aromatic ring.

Reactivity of p-phenyl substituted β-enamino compounds using K- 10/ultrasound. I. Synthesis of pyrazoles and pyrazolinones

The reactivity of the β-enamino ketones, 3-amino-1-(p-phenyl- substituted)-2-buten-1-ones 1a-d and β-enamino esters, ethyl 3-amino-3-(p- phenyl-substituted)-2-propenoates 5a-d was systematically studied when allowed to react with hydrazine and methylhydrazine under solid support K- 10/ultrasound conditions and in homogeneous media (reflux in ethanol or dichloromethane). The products were pyrazoles 2a-d, N-methylpyrazoles 3a-d, 4a-d and N-methylpyrazolinones 6a-c and 7a-c. The regiochemistry of the cyclization reactions showed dependence upon the reaction conditions employed as well as upon the substituent in the aromatic ring.

Process for the preparation of pyrazolones

A process for the preparation of pyrazolone derivatives represented by the general formula STR1 wherein R is a hydrogen atom, an alkyl group, an allyl group, an aryl group or an aralkyl group, and R1 and R2 are, respectively, a hydrogen atom, an alkyl group or a phenyl group which may have a substituent, comprising reacting a 2,3-dihalocarboxylic acid derivative or a 2-haloacrylic acid derivative with a hydrazine derivative. A pyrazolone or 1-substituted-3-pyrazolones useful as intermediate starting materials for the synthesis of agricultural chemicals, medicine and chemical compounds can be easily and cheaply prepared from widely used industrial starting materials.

Cyclocondensation of Alkylhydrazines and β-Substituted Acetylenic Esters: Synthesis of 3-Hydroxypyrazoles

Addition of monosubstituted alkylhydrazines to acetylenic esters with either electron-withdrawing or sterically bulky β-substituents afforded 1-alkyl-3-hydroxy-5-substituted-pyrazoles 1 as the major regioisomeric product.By comparison, the classical cyclo

PHOTOCHEMICAL BENZYL MIGRATION IN 3-PYRAZOLIN-5-ONES

The 3-pyrazolin-5-ones (1) undergo light induced rearrangement by N -> O and N -> C4 benzyl migrations.A free radical mechanism is proposed.