78597-54-3

Usage

Uses

Used in Pharmaceutical Industry:
5-AMINO-3-(4-METHYLPHENYL)PYRAZOLE is used as a starting material for the preparation of bioactive fused polycyclic pyrazoles. It serves as a potential precursor for the synthesis of 2,5-bis(4-methylphenyl)-7-phenyl-6,7-dihydropyrazolo[1,5-a]pyrimidine-3,6-dicarbaldehyde, which can be further utilized in the development of novel pharmaceutical compounds with potential therapeutic applications.
Used in Chemical Synthesis:
5-AMINO-3-(4-METHYLPHENYL)PYRAZOLE is used as a reactant in the synthesis of 4-hetarylpyrazolo[1,5-a][1,3,5]triazines. This synthesis can be carried out under microwave conditions and in the absence of solvent, which offers a more efficient and environmentally friendly approach to producing these heterocyclic compounds.
Used in Organic Chemistry Research:
5-AMINO-3-(4-METHYLPHENYL)PYRAZOLE is used in the synthesis of 5-cyano-6,7-dihydro-3-(4-methylphenyl)-6-oxo-1H-pyrazolo[3,4-b]pyridine-4-carboxylates. This is achieved by reacting the compound with dialkyl dicyanofumarates, resulting in the formation of new heterocyclic structures with potential applications in various fields, including pharmaceuticals and materials science.

InChI:InChI=1/C10H11N3/c1-7-2-4-8(5-3-7)9-6-10(11)13-12-9/h2-6H,1H3,(H3,11,12,13)

Upstream product

• 122-00-9 para-methylacetophenone 
• 40808-08-0 1-Chlor-1-p-tolyl-propen-3-al 
• 7064-35-9 5-(4-methylphenyl)isoxazole 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 7391-28-8 p-tolueneacetonitrile 

Downstream Products

• 1025072-25-6 7-amino-6-cyano-5-(4-chlorophenyl)-2-(4-methylphenyl)-pyrazolo[1,5-a]pyrimidine 
• 1448466-62-3 1,3-dihydro-7-(4-methylphenyl)pyrazolo[1,5-a][1,3,5]triazin-2-thioxo-4-one 

Relevant academic research and scientific papers

Novel benzenesulfonamide-bearing pyrazoles and 1,2,4-thiadiazoles as selective carbonic anhydrase inhibitors

Two series comprising 20 novel benzenesulfonamides bearing thioureido-linked pyrazole 8 and amino-1,2,4-thiadiazole 10 were synthesized and assayed as human carbonic anhydrase (hCA) inhibitors against isoforms I and II as well as the tumor-associated isof

Synthesis and biological evaluation of novel N-(5-phenyl-1H-pyrazol-3-yl)benzenesulfonamide derivatives as potential BRAFV600E inhibitors

A series of novel N-(5-phenyl-1H-pyrazol-3-yl)benzenesulfonamide derivatives (5a–5l) were synthesized and developed as potential BRAFV600E inhibitors. Among them, compound 5l exhibited the most potent inhibitory activity with an IC50

Synthesis of Aminopyrazoles from Isoxazoles: Comparison of Preparative Methods by in situ NMR Analysis

A single-step method and a two-step method for the synthesis of aminopyrazoles from isoxazoles are presented and compared. Based on in situ NMR monitoring, both processes proceed through a ketonitrile. In the single-step process, hydrazine serves to both open the isoxazole to the unisolated ketonitrile intermediate and form the aminopyrazole. The two-step process involves ring opening of the isoxazole by deprotonation with hydroxide to generate the ketonitrile followed by the addition of acetic acid and hydrazine to form the aminopyrazole.

Synthesis, biological evaluation and 3D-QSAR studies of novel 5-phenyl-1 H -pyrazol cinnamamide derivatives as novel antitubulin agents

A series of novel 5-phenyl-1H-pyrazol derivatives (5a-5x) containing cinnamamide moiety were synthesized and their biological activities as potential tubulin polymerization inhibitors were evaluated. Among them, compound 5j exhibited the most potent inhibitory activity with an IC50 value of 1.02 μ1/4M for tubulin, which was superior to that of Colchicine (IC50 Combining double low line 1.34 μ1/4M). Docking simulation was performed to insert compound 5j into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. 3D-QSAR model was also built to provide more pharmacophore understanding that could be used to design new agents with more potent tubulin inhibitory activity.

Study of regioselectivity of reactions between 3(5)-aminopyrazoles and 2-acetylcycloalkanones

Regioselectivity was examined of reactions between nine 3(5)-aminopyrazoles and 2-acetylcyclopentanone and 2-acetylcyclohexanone under various conditions. A series of cyclopenta[e]pyrazolo-[1,5-a]pyrimidines was obtained. The highest regioselectivity of the reaction was observed in alcohol at 20°C in the presence of a catalytic quantity of trifl uoroacetic acid. The regiostructure of compounds was established by 1H and 13C NMR spectroscopy. Pleiades Publishing, Ltd., 2012.