54606-37-0

Usage

Uses

Used in Pharmaceutical Industry:
(5-amino-1-phenyl-1H-pyrazol-4-yl)-phenyl-methanone is used as a precursor for the synthesis of various biologically active compounds due to its unique molecular structure and reactivity. It plays a crucial role in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, (5-amino-1-phenyl-1H-pyrazol-4-yl)-phenyl-methanone is used as a starting material for the creation of compounds with pesticidal, herbicidal, or fungicidal properties. Its versatility in organic synthesis allows for the development of novel agrochemicals to address various agricultural needs.
Used in Chemical Manufacturing Processes:
(5-amino-1-phenyl-1H-pyrazol-4-yl)-phenyl-methanone is used as an important intermediate in chemical manufacturing processes. Its properties and reactivity make it a valuable component in the synthesis of a wide range of chemical products, contributing to the advancement of various industrial applications.

Upstream product

• 64-17-5 ethanol 
• 6123-64-4 3-Anilino-2-benzoyl-propennitril 
• 100-63-0 phenylhydrazine 
• 174652-94-9 1-phenyl-2-cyano-3-dimethylaminopropen-1-one 
• 52200-09-6 2-benzoyl-3-(dimethylamino)-2-propenenitrile 
• 59-88-1 phenylhydrazine hydrochloride 
• 532-27-4 1-chloroacetophenone 
• 614-16-4 Benzoylacetonitrile 

Downstream Products

• 882175-37-3 (5-bromo-1-phenyl-1H-pyrazol-4-yl)phenylmethanone 

Relevant academic research and scientific papers

Microwave-assisted synthesis of 5-aminopyrazol-4-yl ketones and the p38MAPK inhibitor RO3201195 for study in Werner syndrome cells

5-Aminopyrazol-4-yl ketones are prepared rapidly and efficiently using microwave dielectric heating from β-ketonitriles by treatment with N,N′-diphenylformamidine followed by heterocyclocondensation by irradiation with a hydrazine. The inhibitory activity of RO3201195 prepared by this methodology was confirmed in hTERT-immortalized HCA2 and WS dermal fibroblasts at 200 nM concentration, both by ELISA and immunoblot assay, and displays excellent kinase selectivity for p38α MAPK over the related stress-activated kinase JNK.

Discovery of S-[5-amino-1-(4-fluorophenyl)-1H-pyrazol-4-yl]-[3-(2,3- dihydroxypropoxy)phenyl]-methanone (RO3201195), an orally bioavailable and highly selective inhibitor of p38 Map kinase

A novel class of highly selective inhibitors of p38 MAP kinase was discovered from high throughput screening. The synthesis and optimization of a series of 5-amino-N-phenyl-1H-pyrazol-4-yl-3-phenylmethanones is described. An X-ray crystal structure of this series bound in the ATP binding pocket of unphosphorylated p38a established the presence of a unique hydrogen bond between the exocyclic amine of the inhibitor and threonine 106 which likely contributes to the selectivity for p38. The crystallographic information was used to optimize the potency and physicochemical properties of the series. The incorporation of the 2,3-dihydroxypropoxy moiety on the pyrazole scaffold resulted in a compound with excellent drug-like properties including high oral bioavailability. These efforts identified 63 (RO3201195) as an orally bioavailable and highly selective inhibitor of p38 which was selected for advancement into Phase I clinical trials.

Cyanoacetophenone as a synthon for 1,4,5-substituted pyrazoles

An improved synthesis of cyanoacetophenone is described. Cyanoacetophenone was reacted with dimethylformamide-dimethylacetal and diphenylformamidine to give 1-dimethylamino-3-oxo-3-phenyl-1-propene-2-carbonitrile and 1-anilinomethylene-3-oxo-3-phenyl-1-propene-2-carbonitrile. Reaction of 1-dimethylamino-3-oxo-3-phenyl-1-propene-2-carbonitrile with hydrazines gave either 1-substituted 5-amino-4-benzoylpyrazoles or (1-substituted) 4-cyano-5-phenylpyrazoles. Treatment of 1-anilinomethylene-3-oxo-3-phenyl-1-propene-2-carbonitrile with phenylhydrazine also yielded 5-amino-4-benzoyl-1-phenylpyrazole, whereas reaction with unsubstituted hydrazine afforded 4-cyano-5-phenylpyrazole.

Steric and electronic control in the addition of hydrazine and phenylhydrazine to α-[(dimethylamino)methylene]-β-oxoarylpropanenitriles

Reaction of hydrazine with α-[(dimethylamino)methylene]-β-oxoarylpropanenitriles 2 gives a mixture of the 4-aroyl-5-aminopyrazoles 3 and the 5-aryl-4-cyanopyrazoles 4. Similarly reaction of 2 with phenylhydrazine gives rise to the 5-amino-4-aroyl-1-phenylpyrazoles 5 and 5-aryl-4-cyano-1-phenylpyrazoles 6. The regioselectivity of addition has been investigated with respect to the electronic nature and steric requirements of the aromatic substitution. The ratio of products was found to be independent of the electronic nature of the substituent. The outcome of the reaction was however very sensitive to steric factors. Substituents in the para- and meta-positions favoured formation of the pyrazole-nitrile products 4 and 6, whereas sterically demanding ortho-substituents favoured the pyrazole-amino ketones 3 and 5.