4860-93-9

Usage

Uses

Used in Organic Chemistry:
3-Phenyl-5-pyrazolone is used as a versatile building block for the preparation of various organic compounds, contributing to the synthesis of dyes, pharmaceuticals, and other chemical compounds.
Used in Coordination Chemistry:
3-Phenyl-5-pyrazolone is used as a ligand in coordination chemistry, playing a crucial role in the formation of metal complexes and enhancing their properties.
Used in Analytical Chemistry:
3-Phenyl-5-pyrazolone is used as a spectrophotometric reagent for the determination of a variety of metal ions, providing a reliable method for metal ion analysis.
Used in Pharmaceutical Industry:
3-Phenyl-5-pyrazolone is used as a reagent in the synthesis of pharmaceuticals, aiding in the development of new drugs and improving existing ones.
Used in Dye Industry:
3-Phenyl-5-pyrazolone is used as a reagent in the synthesis of dyes, contributing to the creation of new dyes and enhancing the properties of existing ones.

InChI:InChI=1/C9H8N2O/c12-9-6-8(10-11-9)7-4-2-1-3-5-7/h1-6H,(H2,10,11,12)

Upstream product

• 79230-05-0 1H-1-benzoyl-5-hydroxy-3-phenylpyrazole 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 140-87-4 Cyanoacetohydrazide 
• 1846-74-8 3-benzoyl-chromen-2-one 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 4891-38-7 phenylpropynoic acid methyl ester 

Downstream Products

• 41278-87-9 6-amino-3-phenyl-1⁽²⁾H-pyrano[2,3-c]pyrazole-4,4,5-tricarbonitrile 
• 85094-07-1 4-methyl-3-phenyl-1H-pyrano[2,3-c]pyrazol-6-one 
• 89522-21-4 1H-3-phenylpyrazolo<3,4-b>quinoline 
• 89522-20-3 3-({[1-(2-Amino-phenyl)-meth-(Z)-ylidene]-hydrazono}-phenyl-methyl)-1H-quinolin-2-one 
• 89522-22-5 2-[4-(3-Phenyl-pyrazolo[3,4-b]quinolin-1-yl)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-yl]-phenylamine 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 84752-10-3 4-diazo-3-phenyl-2-pyrazolin-5-one 
• 70-55-3 toluene-4-sulfonamide 
• 67000-45-7 2,3-dihydro-6-phenylpyrazolo[3,2-b]oxazole 

Relevant academic research and scientific papers

Synthesis of thiazole, thiophene, pyran and pyridine derivatives derived from 3-phenyl-1h-pyrazol-5(4h)-one with anti-proliferative, tyrosine kinase and pim-1 kinase inhibitions

Background: A wide range of pyrazole derivatives gained special attention due to their wide range of pharmacological activities especially the therapeutic activities. Many pharmacological drugs containing the pyrazole nucleus are known in the market. Method: The 3-phenyl-1H-pyrazol-5(4H)-one was the key starting compound for many heterocyclic reactions to produce substituted and fused pyrazole derivatives. Results: Antiproliferative activities of the produced compounds against six cancer cell lines A549, HT-29, MKN-45, U87MG, and SMMC-7721 and H460 were measured through which compounds showed high inhibitions. The most promising compounds were tested against tyrosine kinases (c-Kit, Flt-3, VEGFR-2, EGFR, and PDGFR). Structure-Activity Relationship (SAR) was rationalized by looking at the varying structural features of the molecules. In addition, the most active compounds were selected for Pim-1 inhibition. Conclusion: Thirty-nine pyrazole derivatives were synthesized. Nine of them 8b, 9, 12b, 12d, 14b, 15b, 18d, 18f, 19b, and 21d were the most active compounds toward the selected cancer cell lines. Compounds 12b, 14b, 18d, 18f, and 21d showed high inhibitions toward the tyrosine kinases, whereas compounds 14b, 18d, and 18f were the most potent inhibitors of Pim-1.

Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones

Twenty five 4-aminomethylidene derivatives obtained from 3-phenyl-2-pyrazolin-5-one and 1,3-diphenyl-2-pyrazolin-5-one were synthesized and tested for their antiproliferative activity against human breast cancer MDA-MB-361 and MDA-MB-453 cell lines. The compounds derived from 1,3-diphenyl-2-pyrazolin-5-one exhibited the most remarkable activity in the treatment of both cell lines. In vitro antiproliferative activities were accompanied by an important apoptotic fraction of both cell lines; also, compounds inhibited key endothelial cell functions implicated in invasion and angiogenesis. QSAR methods were performed in order to analyze the influence of structural features of the compounds investigated on the antiproliferative potential on MDA-MB-361 and MDA-MB-453 cancer cells. One-parameter heuristic analysis was performed and different whole molecule and fragmental descriptors were considered for rationalization of mechanism of interaction of these compounds with active place of hypothetical target included in tumorigenesis.

3-Aryl-4-(arylhydrazono)-1H-pyrazol-5-ones: Highly ligand efficient and potent inhibitors of GSK3β

A series of 3-aryl-4-(arylhydrazono)-1H-pyrazol-5-one inhibitors of GSK3β was developed from a low molecular weight, highly ligand efficient screening hit 1. Hit-to-lead optimization led to a number of highly potent inhibitors, while maintaining the high ligand efficiency of the screening hit.

N,N-dialkyl-N′-chlorosulfonyl chloroformamidines in heterocyclic synthesis. Part VIII. Novel pyrazolo-fused oxathiadiazines and thiatriazoles

N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted with pyrazol-3-ones 2 under a variety of conditions to give pyrazolo[2,3-e][1,2,3,5] oxathiadiazine dioxides 3 and pyrazolo[3,2-b][1,4,3,5]oxathiadiazine dioxides 5, and frequently, one or both of pyrazolo[1,2-b][1,2,3,5]thiatriazole 1,1,5-trioxides 4 and 1,1,7-trioxides 6. In all reactions, the pyrazolo[3,2-b][1,4,3,5]oxathiadiazine 5 was the major product, with the pyrazolo[2,3-e][1,2,3,5]oxathiadiazine 3 being a significant product in the absence of base. Prior to our recent work, the core ring systems of compounds 3 and 5 had not been reported and compounds 4 and 6 are new derivatives of a rare ring system. CSIRO 2010.

Microwave-assisted synthesis of substituted pyrazolones under solvent-free conditions

Condensation of hydrazine derivatives with various β-keto esters under solvent-free conditions using microwave irradiation leads to very rapid formation of pyrazolones with good to excellent yields.

Scaffold oriented synthesis. Part 1: Design, preparation, and biological evaluation of thienopyrazoles as kinase inhibitors

We report the synthesis of kinase targeted libraries based on the thienopyrazole scaffold. Several thienopyrazole analogs have been identified as submicromolar inhibitors of KDR.

Tautomerism-dependent ring construction of N-heterocyclic compounds from the reactions of 1-alkynyl fischer carbene complexes and substituted pyrazolinones

Four types of N-heterocyclic ring systems were successfully constructed from the reactions of 1-alkynyl Fischer carbene complexes (OC) 5M=C(OEt)C≡CPh (1) (M = Cr, W) and substituted pyrazolinones (2). Reactions of 1 with 3-methyl-2-pyrazolin-5-one (2a), 3-n-propyl-2- pyrazolin-5-one (2b), 3,4-dimethyl-2-pyrazolin-5-one (2c), 3,4-trimethylene-2- pyrazolin-5-one (2d), or 3,4-tetramethylene-2-pyrazolin-5-one (2e) generated three kinds of Fischer aminocarbene complexes (3-5), and reactions of 1 with phenyl-substituted pyrazolinones, i.e., 3-phenyl-2-pyrazolin-5-one (2f) and its tautomer 3-phenyl-3-pyrazolin-5-one (2g), gave Fischer alkoxycarbene complexes (6) as the major products and aminocarbene complexes of types 3-5 as the minor products. Multiple tautomerism of pyrazolinones is attributed to the versatile formation of N-heterocyclic Fischer carbene complexes. Oxidative demetalation of complexes 3-6 with pyridine N-oxide or m-chloroperoxybenzoic acid efficiently afforded organic carbonyl products, and thus, strongly fluorescent syn-mixed-bimanes were prepared. The present findings constitute an alternative new method to synthesize mixed bimanes and other novel N-heterocyclic compounds.

Phase-transfer catalyzed alkylation and cycloalkylation of 3-substituted-1H-pyrazol-2-in-5-ones in the absence or presence of carbon disulphide

PTC-alkylation of 3-substituted-1H-pyrazol-2-in-5-ones by different organohalogen reagents at 25°C in the presence of tetrabutylammonium bromide as-catalyst was investigated either in the absence or presence of CS 2. This work aims to study the comparative reactivity of N-versus O-versus C-alkylation and cycloalkylation. Copyright Taylor & Francis Inc.

QUINAZOLINE DERIVATIVES

The invention relates to the use of compounds of the formula I: wherein: ring C is a 5-6 membered heterocyclic moiety; Z is -O-, -S-, or -CH2-; R1 is hydrogen, C1-4alkyl, C1-4alkoxymethyl, di(C1-4)alkoxy)methyl, C1-4alkanoyl, trifluoromethyl, cyano, amino, C2-5alkenyl, C2-5alkynyl, carboxy, C3-7cycloalkyl, C3-7-cycloalkylC1-3alkyl, or an optionally substituted group selected from phenyl, benzyl, phenylC2-4alkyl and a 5-6 membered heterocyclic group; n is an integer from 0 to 5; m is an integer from 0 to 3; R2 represents hydrogen, hydroxy, halgeno, cyano, nitro, trifluoromethyl, C1-3alkyl, C1-3alkoxy, C1-3alkylsulphanyl, -NR3R4 (wherein R3 and R4, which may be the same or different, each represents hydrogen or C1-3alkyl), or R5X1- (wherein X1 represents a direct bond, -CH2-, or a heteroatom linker group and R5 is an alkyl, alkenyl or alkynyl chain optionally substituted by for example hydroxy, amino, nitro, alkyl, cycloalkyl, alkoxyalkyl, or an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring, which alkyl, alkenyl or alkynyl chain may have a heteroatom linker group, or R5 is an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring, and salts thereof, in the manufacture of a medicament for use in the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals, processes for the preparation of such compounds, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and compounds of formula I. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.

Conversion of coumarins accompanied by opening and recyclization of the lactone ring. 1. Study of the reaction of 3-ethoxycarbonyl(3-acyl)coumarins with cyanoacetylhydrazine and its derivatives

A stepwise sequence for the interaction of 3-ethoxycarbonyl(acyl)coumarins with cyanoacetylhydrazine, its N-acetyl and N-isopropylidene derivatives, leading to the formation of 3-cyanocoumarins, is proposed and demonstrated. It was established that the 3-cyanocoumarins formed are also able to participate in further conversions by a type of Michael reaction.