1572-10-7

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Amino-5-phenylpyrazole is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its versatile chemical structure allows it to be a key component in the creation of different drug molecules.
Used in Organic Chemistry:
In the field of organic chemistry, 3-Amino-5-phenylpyrazole is used as a building block for the synthesis of various organic compounds. Its reactivity and functional groups make it a valuable asset in the synthesis of complex organic molecules.
Used in the Synthesis of Urea Derivatives:
3-Amino-5-phenylpyrazole is used as a reactant for the synthesis of urea derivatives by reacting with azido(6-(benzofuran-2-yl)-2-methylpyridin-3-yl) methanone. This application is particularly useful in the development of new compounds with potential biological activities.
Used in the Synthesis of 2-Mercaptoacetamide Analogs:
It is also used in the synthesis of 2-mercaptoacetamide analogs by treating with thioglycolic acid. This application can lead to the development of new therapeutic agents with potential applications in medicine.
Used in the Synthesis of 3-(Substituentpyrimidayl)-5,6-Benzocoumarins:
3-Amino-5-phenylpyrazole is used as a reactant for the synthesis of 3-(substituentpyrimidayl)-5,6-benzocoumarins by treating with 3-(2′-formyl-1′-chlorovinyl)-5,6-benzocoumarin. This application can contribute to the development of novel compounds with potential applications in various industries.
Used in the Synthesis of Substituted 2,7-Diphenylpyrazolo[1,5-a]pyrimidine-5-Carboxylic Esters:
It is used as a reactant for the synthesis of substituted 2,7-diphenylpyrazolo[1,5-a]pyrimidine-5-carboxylic esters by reacting with substituted β-diketo esters. This application can lead to the creation of new compounds with potential uses in various fields.
Used in the Synthesis of N-Ethoxycarbonylthiourea Derivatives:
3-Amino-5-phenylpyrazole is used as a reactant for the synthesis of N-ethoxycarbonylthiourea derivatives by reacting with ethoxycarbonyl isothiocyanate. This application can result in the development of new compounds with potential applications in various industries.
Used in the Synthesis of Heterobiaryl Pyrazolo[3,4-b]pyridines:
It is used as a reactant for the synthesis of heterobiaryl pyrazolo[3,4-b]pyridines by reacting with indole-3-carboxaldehyde. This application can contribute to the development of novel heterocyclic compounds with potential applications in various fields.

InChI:InChI=1/C9H9N3/c10-9-6-8(11-12-9)7-4-2-1-3-5-7/h1-6H,(H3,10,11,12)

Upstream product

• 2492-30-0 acetophenone semicarbazone 
• 925-90-6 ethylmagnesium bromide 
• 935-02-4 3-Phenyl-2-propynonitrile 
• 19521-13-2 erythro-2,3-dibromo-3-phenylpropanenitrile 
• 2825-34-5 3-amino-5-phenylisothiazole 
• 1187734-02-6 4-bromo-3-hydrazinyl-5-phenylisothiazole 
• 19993-34-1 4-bromo-3-chloro-5-phenylisothiazole 
• 19983-39-2 3-chloro-5-phenylisothiazole 
• 90792-75-9 3-amino-4-bromo-5-phenylisothiazole 
• 78583-84-3 3-chloro-3-phenylprop-2-enenitrile 
• 98-86-2 acetophenone 
• 33603-87-1 β-chlorocinnamaldehyde 
• 70-11-1 α-bromoacetophenone 
• 93-58-3 benzoic acid methyl ester 

Downstream Products

• 65774-94-9 6-methyl-7-oxo-2-phenyl-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 
• 50671-40-4 N-(5-phenyl-1H-pyrazol-3-yl)acetamide 
• 65774-92-7 5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 36931-77-8 2,5-diphenylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 36931-80-3 3-oxo-3-phenyl-propionic acid-(5-phenyl-1⁽²⁾H-pyrazol-3-ylamide) 
• 179184-84-0 N-(2-benzoyl-5-phenyl-2H-pyrazol-3-yl)-benzamide 
• 115231-49-7 2,4-diamino-7-phenylpyrazolo[1,5-a][1,3,5]triazine 
• 197367-84-3 7-amino-2-phenyl-4H-pyrazolo[1,5-a]pyrimidin-5-one 
• 64861-26-3 2,6-diphenyl-4H-pyrazolo[1,5-a]pyrimidine-5,7-dione 
• 87119-67-3 5,7-Dimethyl-2-phenylpyrazolo<1,5-a>pyrimidine 
• 37132-92-6 N-(5-phenyl-1⁽²⁾H-pyrazol-3-yl)-malonamic acid ethyl ester 
• 21684-57-1 N,N'-bis-(5-phenyl-1⁽²⁾H-pyrazol-3-yl)-malonamide 
• 109644-28-2 3,5-diphenyl-1,7-dihydro-dipyrazolo[3,4-b;4',3'-e]pyridine 
• 65774-93-8 7-oxo-2-phenyl-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

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.

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

Gramine-based structure optimization to enhance anti-gastric cancer activity

Gramine is a natural indole alkaloid with a wide range of biological activities, but its anti-gastric cancer activity is poor. Herein, a pharmacophore fusion strategy was adopted to design and synthesize a new series of indole-azole hybrids on the structural basis of gramine. Based on our previous studies, different nitrogen-containing five-membered heterocyclic rings and terminal alkyne group were introduced into the indole-based scaffold to investigate their effect on improving the anti-gastric cancer activity of gramine derivatives. Structure-activity relationship (SAR) studies highlighted the role played by terminal alkyne in enhancing the inhibitory effect, and compound 16h displayed the best antiproliferative activity against gastric cancer MGC803 cells with IC50 value of 3.74 μM. Further investigations displayed compound 16h could induce mitochondria-mediated apoptosis, and caused cell cycle arrest at G2/M phase. Besides, compound 16h could inhibit the metastasis ability of MGC803 cells. Our studies may provide a new strategy for structural optimization of gramine to enhance anti-gastric cancer activity, and provide a potential candidate for the treatment of gastric cancer.

Discovery of 2,4-diaminopyrimidine derivatives targeting p21-activated kinase 4: Biological evaluation and docking studies

In this study, novel 2,4-diaminopyrimidine derivatives targeting p21-activated kinase 4 (PAK4) were discovered and evaluated for their biological activity against PAK4. Among the derivatives studied, promising compounds A2, B6, and B8 displayed the highest inhibitory activities against PAK4 (IC50 = 18.4, 5.9, and 20.4 nM, respectively). From the cellular assay, compound B6 exhibited the highest potency with an IC50 value of 2.533 μM against A549 cells. Some compounds were selected for computational ADME (absorption, distribution, metabolism, and elimination) properties and molecular docking studies against PAK4. The detailed structure–activity relationship based on the biochemical activities and molecular docking studies were explored. According to the docking studies, compound B6 had the lowest docking score (docking energy: ?7.593 kcal/mol). The molecular docking simulation indicated the binding mode between compound B6 and PAK4. All these results suggest compound B6 as a useful candidate for the development of a PAK4 inhibitor.

Synthesis of aminopyrazole analogs and their evaluation as CDK inhibitors for cancer therapy

We synthesized a library of aminopyrazole analogs to systematically explore the hydrophobic pocket adjacent to the hinge region and the solvent exposed region of cyclin dependent kinases. Structure-activity relationship studies identified an optimal substitution for the hydrophobic pocket and analog 24 as a potent and selective CDK2/5 inhibitor.

Synthesis, biological evaluation and molecular docking of novel 5-phenyl-1H-pyrazol derivatives as potential BRAFV600E inhibitors

The RAF-MEK-ERK cascade appears to be intimately involved in the regulation of cell cycle progression and apoptosis. The BRAFV600E mutant results in constitutive activation of the ERK pathway, which can lead to cellular growth dysregulation. A series of 5-phenyl-1H-pyrazol derivatives (3a-5e) have been designed and synthesized, and their biological activities were evaluated as potential BRAFV600E inhibitors. All the compounds were reported for the first time except 3e, and compound 1-(4-bromo-2-hydroxybenzyl)- 3-phenyl-1-(5-phenyl-1H-pyrazol-3-yl)urea (5c) displayed the most potent inhibitory activity (BRAFV600E IC50 = 0.19 μM). Antiproliferative assay results indicated that compound 5c possessed high antiproliferative activity against cell lines WM266.4 and A375 in vitro, with IC50 values of 1.50 and 1.32 μM, respectively, which were comparable with the positive control vemurafenib. Docking simulations showed that compound 5c binds tightly to the BRAFV600E active site and acts as BRAFV600E inhibitor. A 3D-QSAR model was also built to provide more pharmacophore understanding towards designing new agents with more potent BRAFV600E inhibitory activity.

Synthesis of pyrazolo[1,5-a][1,3,5]triazine derivatives as inhibitors of thymidine phosphorylase

Thymidine phosphorylase (TP) is an enzyme that promotes tumor growth and metastasis and therefore is an attractive druggable target. Using a reported TP inhibitor, 7-deazaxanthine (7DX), as the lead compound; this study was set up to evaluate whether pyrazolo[1,5-a][1,3,5]triazin-2,4-diones and pyrazolo[ 1,5- a][1,3,5]triazin-2-thioxo-4-ones would exhibit TP inhibitory activity. The pyrazolo[1,5-a][1,3,5] triazine nucleus was constructed using a reaction that annulated the 1,3,5-triazine ring onto a pyrazole scaffold. Among the 52 compounds synthesized and tested, it was found that 1,3-dihydro-pyrazolo[1,5-a] [1,3,5]triazin-2-thioxo-4-ones exhibited various extent of inhibitory activity against TP. The best compound 17p, which bears a para-substituted pentafluorosulfur group, showed an IC50 value of 0.04 μM, which was around 800 times more potent than the 7DX (IC50 = 32 μM) under the same bioassay conditions. The results of the study suggested that a substituent with +σ and +π properties inserted at position 4 of a phenyl ring that is attached to position 8 of the pyrazolo[1,5-a][1,3,5]triazin- 2-thioxo-4-one scaffold would give excellent TP inhibitory action. In addition, 17p was found to be a non-competitive inhibitor thus suggested that it might interact with TP at a position different from the substrate binding site.

Reaction of 6-methyl-2-(2-oxo-2-phenyl-ethylidene)-2,3-dihydropyrimidin- 4(1H)-one with hydrazine and hydroxylamine

The reaction of 6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin- 4(1H)-one and of its nitrosation product with hydroxylamine stops at the stage of forming the corresponding oximes. The reaction of 6-methyl-2-(2-oxo-2- phenylethylidene)-2,3-dihydropyrimidin-4(1H)-one with hydrazine yields a mixture of 3-amino-5-phenylpyrazole and 3-methyl-2-pyrazolin-5-one in 71 and 62% yields, respectively. The ketoxime is used in the synthesis of a series of imidazole N(3)-oxides substituted at the 1, 4, and 5 positions of the imidazole ring.

Unexpected reaction course of 3-Amino-5-aryl-1H-pyrazoles with dialkyl dicyanofumarates

On treatment of 3-amino-5-aryl-1H-pyrazoles 1 with dialkyl dicyanofumarates (=(E)-but-2-enedioates) 4 in boiling 1,2-dichloroethane, two competitive reactions occurred leading to 3-aryl-5-cyano-6,7-dihydro-6-oxo-1H-pyrazolo[3,4- b]pyridine-4-carboxylates

The conversion of isothiazoles into pyrazoles using hydrazine

The conversion of isothiazoles into pyrazoles on treatment with hydrazine is investigated. The influence of various C-3, C-4 and C-5 isothiazole substituents and some limitations of this ring transformation are examined. When the isothiazole C-3 substituent is a good nucleofuge, 3-aminopyrazoles are obtained. However, when the 3-substituent is not a leaving group it is retained in the pyrazole product. Treatment of 4-bromo-3-chloro-5-phenylisothiazole 56 or 3-chloro-4,5-diphenylisothiazole 57 with anhydrous hydrazine at ca. 200 °C for a few minutes gives the corresponding 3-hydrazinoisothiazoles 61 and 64 respectively in high yields; the stability of these new hydrazines is investigated. 5,5′-Diphenyl-3,3′-biisothiazole-4,4′-dicarbonitrile 78 reacts with hydrazine to give 5,5′-diphenyl-3,3′-bi(1H-pyrazole)-4,4′-dicarbonitrile 79. Methylhydrazine reacts with 3-chloro-5-phenylisothiazole-4-carbonitrile 1 to give 3-(1-methylhydrazino)-5-phenylisothiazole-4-carbonitrile 83 and 3-amino-1-methyl-5-phenylpyrazole-4-carbonitrile 84. All products are fully characterised and rational mechanisms for the isothiazole into pyrazole transformation are proposed.