2538-52-5

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
1,3-Diphenyl-2-pyrazoline serves as a reactant in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides due to its chemical reactivity and structural properties.
Used in Biomedical Research:
As a fluorescent probe, 1,3-Diphenyl-2-pyrazoline is utilized for the detection of free radicals in biological systems, aiding in the study of oxidative stress and related pathological conditions.
Used in Medicinal Chemistry:
1,3-Diphenyl-2-pyrazoline's potential antioxidant properties make it a subject of interest for research in medicinal chemistry, where it may contribute to the development of treatments targeting oxidative stress-related diseases.
Used in Drug Development:
Its cytotoxic properties are under investigation for potential applications in drug development, particularly in the creation of compounds that can target and eliminate cancer cells or other harmful cellular processes.

InChI:InChI=1/C15H14N2/c1-3-7-13(8-4-1)15-11-12-17(16-15)14-9-5-2-6-10-14/h1-10H,11-12H2

Upstream product

• 110-86-1 pyridine 
• 936-53-8 1-phenyl-4,5-dihydro-1H-pyrazole 
• 100-34-5 benzene diazonium chloride 
• 4492-01-7 1,3-diphenyl-1H-pyrazole 
• 13993-24-3 1,4-bis(2-benzoylethyl)piperazine 
• 100-63-0 phenylhydrazine 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 7334-41-0 3-acetoxypropiophenone 
• 936-59-4 3-chloropropiophenone 
• 5650-41-9 3-hydroxy-1-phenylpropan-1-one 
• 768-03-6 Phenyl vinyl ketone 
• 3506-36-3 3-dimethylaminopropiophenone 
• 105486-40-6 Phenyl-(1-phenyl-cyclopropyl)-diazene 

Downstream Products

• 105257-97-4 3-phenyl-1-(4-phenylazo-phenyl)-4,5-dihydro-1H-pyrazole 
• 105257-98-5 (4-Nitro-phenyl)-[4-(3-phenyl-4,5-dihydro-pyrazol-1-yl)-phenyl]-diazene 
• 105257-96-3 (4-Methoxy-phenyl)-[4-(3-phenyl-4,5-dihydro-pyrazol-1-yl)-phenyl]-diazene 
• 79913-09-0 4-Phenyl-2-[4-(3-phenyl-4,5-dihydro-pyrazol-1-yl)-phenyl]-[1,3]dithiol-1-ylium; iodide 
• 137116-98-4 1-phenyl-3-<4'-(3-phenyl-4,5-dihydropyrazol-1-yl)biphenyl-4-yl>aminopropan-1-one 
• 83428-92-6 1,1'-(4,4'-biphenylene)bis<3-phenyl-2-pyrazoline> 
• 137117-00-1 N-<4'-(3-phenyl-4,5-dihydropyrazol-1-yl)biphenyl-4-yl>acetamide 
• 137117-01-2 N-<4'-(3-phenylpyrazol-1-yl)biphenyl-4-yl>acetamide 

Relevant academic research and scientific papers

Utility of Ketonic Mannich Bases in Synthesis of Some New Functionalized 2-Pyrazolines

The styryl ketonic Mannich base 2 has been used as a precursor in the synthesis of 2-pyrazolines having a basic side chain at C-3 and a phenolic Mannich base at C-5. Treatment of the bis(styryl ketonic bases) 6a and 8a with phenylhydrazine affords the bis(3-functionalized 2-pyrazolines) 7 and 9. The transamination between the styryl keto base 10 and 4-aminoantipyrine leads to 12, which reacts with piperazine to give 13. N-Nitrosation of the sec-Mannich bases 15a–d followed by reductive cyclization affords 2-pyrazolines 17a–d. The keto base 14b has been used for the synthesis of 2-pyrazolines having a phenolic Mannich base at C-3 and its reaction with 3,5-dimethyl-1H-pyrazole affords 23. The alkylation of 3-methyl-1-phenyl-2-pyrazolin-5-one with the bis(Mannich base) 25 was investigated.

Practical synthesis of pyrazoles via a copper-catalyzed relay oxidation strategy

Various 1,3- and 1,3,4-substituted pyrazoles are smoothly formed via copper-catalyzed cascade reactions of oxime acetates, amines and aldehydes. This relay oxidative process involves copper-promoted N-O bond cleavage and C-C/C-N/N-N bond formations to furnish pyrazolines, and sequential Cu-O2 system-involved oxidative dehydrogenation of pyrazolines to afford pyrazoles. This transformation provides a novel and versatile approach for the synthesis of pyrazoles, with an inexpensive copper catalyst and green oxidants. It is atom- and step-economical, and possesses a good functional group tolerance, as well as operational simplicity. This journal is

A novel methodology for synthesis of dihydropyrazole derivatives as potential anticancer agents

A novel, simple, and efficient method for the synthesis of 4,5-dihydropyrazole derivatives has been developed. The reaction proceeded through the base-induced isomerization of easily accessible propargyl alcohols followed by cyclization of α,β-unsaturated hydrazones. Furthermore, selected compounds 3ab and 3ac exhibited good activities against Bel-7404 (human hepatoma cancer), HepG2 (human liver cancer), NCI-H460 (human lung cancer) and SKOV3 (human ovarian cancer) cell lines with IC50 in the range of 22-46 μmol L-1.

Metal-organic frameworks (MOFs) as heterogeneous catalysts for the chemoselective reduction of carbon-carbon multiple bonds with hydrazine

The as-synthesized metal-organic frameworks (MOFs), particularly that based on aluminium coordinated with benzenedicarboxylic acid, constitute selective catalysts for the reduction of carbon-carbon multiple bonds in alkenes, alkynes and α,β-unsaturated esters with hydrazine hydrate in acetonitrile under mild conditions. The present protocol enjoys advantages such as convenient reaction conditions and benign, reusable and cost effective catalyst.

Mannich bases as synthetic intermediates: Alkylation of amines and diamines with bis-ketonic Mannich bases

The bis-ketonic Mannich base, N,N-bis(β-benzoylethyl)methylamine hydrochloride (1) reacts with primary arylamines and diamines to give ketonic sec-arylamines 3a-e and 4. The piperidines 7a-c were obtained from 1 and primary alkylamines, whereas the 1,4-diazepine derivative 10 was obtained from 1 and ethylenediamine. Treatment of the bis-base l,4-di[β-(N-morpholino) propionyl]benzene bis(hydrochloride) (11) with primary arylamines gave the corresponding bis-(sec-arylamines) 12a - b, whereas its reaction with o-phenylenediamine afforded the bis[1,5-benzodiazepine] ring system 14. The synthesis of the diazacyclophane ring system 15 has been achieved by treating 11 with piperazine. Attempted synthesis of 4-aza-[7]-paracyclophane (16) from 11 and benzylamine led to 17. The reaction of 1 or 11 with phenylhydrazine gave the 2-pyrazolines 18 and 19. Treatment of 3 or 4 with phenylhydrazine and formaldehyde afforded the 2H-1,2,4-triazepines 20a-c and the bis[2H-1,2,4-triazepine] ring system 21.

Conversion of 3-benzoyl-1-methyl-4-phenyl-γ-piperidol by arylamines and arylhydrazines. Synthesis of 3-arylamino-1-oxo-1-phenylpropanes and 1,3-diarylpyrazoles and their fragmentation under electron impact

It has been established that on heating, 3-benzoyl-4-hydroxy-1-methyl-4- phenylpiperidine is ring-opened in the presence of arylamines by a type of retroaldol reaction, with subsequent transamination of the intermediate Mannich base and the formation of 3-arylamino-1-oxo-1-phenylpropanes. When using arylhydrazines this γ-piperidol is recyclized with the formation of 1,3-diarylpyrazoles and their 4,5-dihydro derivatives. The mass spectral behavior of a series of 3-arylamino-substituted 1-phenylpropanones has been studied.

Reaction of 3-benzoyl-1-methyl-4-phenyl-γ-piperidol with arylamines and arylhydrazines. Synthesis of 3-arylamino-1-oxo-1-phenylpropanes and 1,3 diarylpyrazoles and their fragmentation under electron impact

Upon heating in the presence of arylamines 3-benzoyl-4-hydroxy-1-methyl-4- phenylpiperidine decyclizes via a retroaldol type reaction with subsequent transamination of the intermediate Mannich base to give 3-arylamino-1-oxo-1- phenylpropanes. In the case of the use of arylhydrazines this γ-piperidol recyclizes to give 1,3-diarylpyrazoles and their 4,5-dihydro derivatives. The mass spectroscopic behavior of a series of 3-arylamino-substituted 1-phenylpropanones has been studied.

Transformations of mono- and bisphenylhydrazones of aliphatic-aromatic 1,5-diketones under the conditions of the fischer reaction

The mono- and bisphenylhydrazones of 3-R-1,5-diphenylpentane-1,5-diones were obtained, and their transformations in the Fischer indole synthesis under various conditions were studied. It was shown that 4-R-2,6-diphenylpyridines, 2-phenylindole, and 5-R-1,-3-diphenyl-Δ2-pyrazolines are formed as the main products in addition to the 3-R-1-phenyl-3-(2-phenyl-3-indolyl)propan-1-ones or their phenylhydrazones produced as a result of indolization. The ways of formation of these compounds are discussed. Some transformations of the obtained ketones were studied.

Addition Products of Hydrazine Derivatives to Azo-Alkenes, Part V: The Reaction of α-(1-Phenylhydrazino)alkanone Phenylhydrazones with Acids and Acid Derivatives

The bifunctional title compounds 2 react with acylating, carbamoylating and sulfonylating reagents mostly at the primary amino group of the hydrazine function.Both functional groups of 2 are attacked by N,N'-carbonyldiimidazole converting it into 1H-1,2,4

Oxidative Cyclization of β-Stannyl Hydrazones

Oxidation of β-stannyl hydrazones gave the corresponding azocyclopropanes in high yields.Homolytic cyclization involving hydrazonyl radicals (?-iminamino radicals) was postulated.