42754-61-0

Usage

Uses

Used in Medicinal Chemistry and Pharmaceutical Industry:
3-AMINO-5-PHENYL-1H-PYRAZOLE-4-CARBONITRILE is used as a key intermediate for the synthesis of new drugs and bioactive molecules, given its unique chemical structure and properties. It plays a crucial role in the development of pharmaceutical products, contributing to the advancement of medicinal chemistry.
Used in Research and Development:
In the realm of research and development, 3-AMINO-5-PHENYL-1H-PYRAZOLE-4-CARBONITRILE is utilized as a valuable building block for the synthesis of diverse organic compounds. It aids in the exploration of chemical reactions and the creation of new compounds, thereby enhancing the understanding of chemical processes and contributing to scientific innovation.
Used in Academic and Industrial Laboratories:
3-AMINO-5-PHENYL-1H-PYRAZOLE-4-CARBONITRILE is employed in academic and industrial laboratories for the study of chemical reactions and the synthesis of new compounds. Its application in these settings facilitates the discovery of novel chemical entities and the optimization of existing synthetic routes, furthering the frontiers of chemical research and application.

Upstream product

• 42754-56-3 2-(methoxyphenylmethylene)malononitrile 
• 46177-21-3 2-benzoylmalononitrile 
• 28989-23-3 3-chloro-5-phenyl-1,2-thiazole-4-carbonitrile 
• 18174-82-8 3-methoxy-5-phenylisothiazole-4-carbonitrile 
• 915395-62-9 3-iodo-5-phenylisothiazole-4-carbonitrile 
• 915395-63-0 3-(benzylamino)-5-phenylisothiazole-4-carbonitrile 
• 1187733-93-2 3-(N-benzylamino)-5-phenyl-1H-pyrazole-4-carbonitrile 
• 20943-38-8 3-amino-5-phenylisothiazole-4-carbonitrile 
• 647016-68-0 3-bromo-5-phenylisothiazole-4-carbonitrile 
• 36778-07-1 3-hydroxy-5-phenylisothiazole-4-carbonitrile 
• 100-52-7 benzaldehyde 
• 109-77-3 malononitrile 
• 60776-91-2 2-(ethoxy(phenyl)methylene)malononitrile 
• 98-88-4 benzoyl chloride 

Downstream Products

• 88796-45-6 3-nitro-7-phenyl-8-cyanopyrazolo<1,5-a>pyrimidine 
• 1174037-73-0 2-phenyl-5-(2-thienyl)pyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile 
• 1174037-76-3 C₁₈H₉N₅S 
• 1174037-70-7 2-phenyl-7-(2-thienyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile 
• 1187733-93-2 3-(N-benzylamino)-5-phenyl-1H-pyrazole-4-carbonitrile 
• 1187733-96-5 1-benzyl-3-(dibenzylamino)-5-phenyl-1H-pyrazole-4-carbonitrile 
• 1187733-95-4 3-(benzylideneamino)-5-phenyl-1H-pyrazole-4-carbonitrile 
• 137470-07-6 5-Amino-3-cyano-7-furan-2-yl-2-phenyl-6,7-dihydro-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester 
• 130867-76-4 3-Amino-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5-phenyl-1H-pyrazole-4-carbonitrile 
• 130867-72-0 5-Amino-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-phenyl-1H-pyrazole-4-carbonitrile 
• 137470-04-3 5-Amino-7-furan-2-yl-2-phenyl-6,7-dihydro-pyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile 
• 137470-05-4 5-Amino-2-phenyl-7-thiophen-2-yl-6,7-dihydro-pyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile 
• 15568-32-8 N-(4-cyano-3-phenyl-1H-pyrazol-5-yl)acetamide 
• 91099-29-5 3-cyano-4,5-dihydro-7-methyl-2-phenyl-5-oxopyrazolo<1,5-a>-pyrimidine 

Relevant academic research and scientific papers

Three-component synthesis of 5-aryl-3-amino-1H-pyrazole-4-carbonitriles and 3-amino-1,2-diazaspiro[4.5]dec-3-ene-4-carbonitriles

A multicomponent method of the synthesis of 5-aryl-3-amino-1H-pyrazole-4-carbonitrile and 3-amino-1,2-diazaspiro[4.5]dec-3-ene-4-carbonitriles with thermal and microwave activation was developed.

Preparation method of 5-amino-4-cyanopyrazole

The invention belongs to the field of organic chemistry, relates to a preparation method of 5-amino-4-cyanopyrazole, and discloses a preparation method of 5-amino-4-cyanopyrazole. According to the invention, a series of 5-amino-4-cyanopyrazole are prepare

Synthesis and in-vitro anti-proliferative evaluation of some pyrazolo[1,5-a]pyrimidines as novel larotrectinib analogs

A series of 2-phenyl-7-(aryl)pyrazolo[1,5-a]pyrimidine-3-carbonitriles 11a–j and 2-phenyl-7-(aryl)pyrazolo[1,5-a]pyrimidine-3,6-dicarbonitriles 16a–c was synthesized by the reaction of 5-amino-3-phenyl-1H-pyrazole-4-carbonitrile (5) with 3-(dimethylamino)

Regioselective Synthesis of Highly Functionalized Pyrazoles from N-Tosylhydrazones

A regioselective synthesis of highly functionalized pyrazoles from N-tosylhydrazones was developed. The reaction was general for a wide range of substrates and demonstrated excellent tolerance to a variety of substituents, and the method has been successfully applied to the formal synthesis of ibrutinib.

Discovery of pyrazolo[1,5-a]pyrimidine-3-carbonitrile derivatives as a new class of histone lysine demethylase 4D (KDM4D) inhibitors

Herein we report the discovery of a series of new small molecule inhibitors of histone lysine demethylase 4D (KDM4D). Molecular docking was first performed to screen for new KDM4D inhibitors from various chemical databases. Two hit compounds were retrieved. Further structural optimization and structure-activity relationship (SAR) analysis were carried out to the more selective one, compound 2, which led to the discovery of several new KDM4D inhibitors. Among them, compound 10r is the most potent one with an IC50 value of 0.41?±?0.03?μM against KDM4D. Overall, compound 10r could be taken as a good lead compound for further studies.

Novel biocompatible glucose-based deep eutectic solvent as recyclable medium and promoter for expedient multicomponent green synthesis of diverse three and four substituted pyrazole-4-carbonitrile derivatives

A novel biocompatible glucose-based deep eutectic solvent (DES) is reported for the first time in the multicomponent synthesis of diverse three and four substituted pyrazole-4-carbonitrile derivatives under catalyst-free condition without using any harmful organic solvent even for purification of the products. The desired products were obtained with high degree of diversity from the reaction of malononitrile, aromatic aldehydes and various hydrazine derivatives as nitrogen source at room temperature within short reaction times and good to excellent product yields. The deep eutectic solvent was also recycled and reused at least four times with only a slight loss of efficiency. A plausible mechanism was also proposed indicating the role of DES hydrogen bonding in the reaction promotion.

Synthesis of 2,5,7-triaryl-4,7(6,7)-dihydropyrazolo[1,5-a]pyrimidine-3- carbonitriles by reaction of 5(3)-amino-3(5)-aryl-1H-pyrazole-4-carbonitriles with chalcones

The reaction of 5(3)-amino-3(5)-aryl-1H-pyrazole-4-carbonitriles with 1,3-diaryl-2-propen-1-ones (chalcones) in refluxing DMF leads to 2,5,7-triaryl-4,7(6,7)-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitriles. In DMSO solution, the latter exist in equilibri

1,3-disubstituted-4-aminopyrazolo [3, 4-d] pyrimidines, a new class of potent inhibitors for phospholipase D

Phospholipase D enzymes cleave lipid substrates to produce phosphatidic acid, an important precursor for many essential cellular molecules. Phospholipase D is a target to modulate cancer-cell invasiveness. This study reports synthesis of a new class of phospholipase D inhibitors based on 1,3-disubstituted-4-amino-pyrazolopyrimidine core structure. These molecules were synthesized and used to perform initial screening for the inhibition of purified bacterial phospholipase D, which is highly homologous to the human PLD1. Initially tested with the bacterial phospholipase D enzyme, then confirmed with the recombinant human PLD1 and PLD2 enzymes, the molecules presented here exhibited inhibition of phospholipase D activity (IC50) in the low-nanomolar to low-micromolar range with both monomeric substrate diC4PC and phospholipid vesicles and micelles. The data strongly indicate that these inhibitory molecules directly block enzyme/vesicle substrate binding. Preliminary activity studies using recombinant human phospholipase Ds in in vivo cell assays measuring both transphosphatidylation and head-group cleavage indicate inhibition in the mid- to low-nanomolar range for these potent inhibitory novel molecules in a physiological environment. This study reports synthesis of a new class of PLD inhibitors based on 1,3-disubstituted-4-amino-pyrazolopyrimidine core structure. These molecules exhibited inhibition of human recombinant PLD activity (IC 50) in the low-nanomolar to low-micromolar range with monomeric substrate diC4PC and phospholipid vesicles and micelles. Preliminary activity studies using recombinant human PLDs in in vivo cell assays measuring both transphosphatidylation and head-group cleavage indicates inhibition in the mid- to low-nanomolar range for these potent inhibitory novel molecules in a physiological environment.

Pyrazolo[3,4-d]pyrimidine analogues: Synthesis, characterization and their in vitro antiamoebic activity

Pyrazolo[3,4-d]pyrimidine analogues were synthesized by treating 3-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-amine with different sulfonyl chlorides and triethylamine in dry dichloromethane. The structure of all the compounds was elucidated by spectral data a

Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities

A series of two classes of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates were synthesized using click chemistry approach. All compounds were evaluated for inhibition of Src kinase and human ovarian adenocarcinoma (SK-Ov-3), breast carcinoma (MDA-MB