51516-71-3

Basic information

• Product Name: 5-amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile
• Synonyms: 5-amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile
• CAS NO: 51516-71-3
• Molecular Formula: C₁₀H₇FN₄
• Molecular Weight: 202.1877832
• Mol File: 51516-71-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 405.546 °C at 760 mmHg
• Flash Point: 199.067 °C
• Appearance: /
• Density: 1.36
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile(51516-71-3)
• EPA Substance Registry System: 5-amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile(51516-71-3)

Safety Data

• Hazardous Substances Data: 51516-71-3(Hazardous Substances Data)

Usage

General Description

5-Amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile, is an organic compound with the chemical formula C10H7FN4. It is a pyrazole derivative with a carbonitrile functional group, and it is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. 5-Amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile has potential biological activities and is of interest in drug discovery and development. It is soluble in organic solvents such as acetone and chloroform, and it is important to handle this compound with caution as it may pose health and environmental hazards if not properly managed.

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 658-27-5 m-fluorophenylhydrazine 
• 109-77-3 malononitrile 
• 2924-16-5 3-fluorophenylhydrazine hydrochloride 
• 123-06-8 Ethoxymethylenemalononitrile 
• 372-19-0 meta-fluoroaniline 

Downstream Products

• 650628-62-9 1-(3-fluorophenyl)-4-hydrazino-1H-pyrazolo[3,4-d]pyrimidine 
• 1269702-96-6 4-chloro-1-(3-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidine 
• 864871-85-2 1-(3-fluoro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one 
• 1456790-23-0 5-[5-amino-1-(3′-fluorophenyl)-1H-pyrazole-4-yl]-1H-tetrazole 
• 1452871-45-2 C₁₄H₁₂FN₅O 
• 1452871-42-9 C₁₃H₁₀FN₅O 
• 1350554-94-7 4-(4,5-dihydro-1H-imidazol-2-yl)-1-(3-fluorophenyl)-1H-pyrazole 
• 1269291-95-3 1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile 
• 1350554-99-2 5-amino-4-(4,5-dihydro-1H-imidazol-2-yl)-1-(3-fluorophenyl)-1H-pyrazole 
• 50427-74-2 5-amino-1-(3-fluoro-phenyl)-1H-pyrazole-4-carboxylic acid amide 
• 135108-58-6 4-Amino-1-(3-fluoro-phenyl)-5-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 

Relevant articles and documents

Synthesis of pyrazole-carboxamides and pyrazole-carboxylic acids derivatives: Simple methods to access powerful building blocks

Hybrid systems containing pyrazole moiety show a wide spectrum of biological activities. To access novel hybrids with pyrazole ring, in this work we synthesized twenty pyrazole-carboxylic acids and twenty pyrazole-carboxamides, using simple synthetic methods, to be used as building blocks in the development of new structures.

Computer-aided molecular design of pyrazolotriazines targeting glycogen synthase kinase 3

Numerous studies have highlighted the implications of the glycogen synthase kinase 3 (GSK-3) in several processes associated with Alzheimer’s disease (AD). Therefore, GSK-3 has become a crucial therapeutic target for the treatment of this neurodegenerative disorder. Hereby, we report the design and multistep synthesis of ethyl 4-oxo-pyrazolo[4,3-d][1–3]triazine-7-carboxylates and their biological evaluation as GSK-3 inhibitors. Molecular modelling studies allow us to develop this new scaffold optimising the chemical structure. Potential binding mode determination in the enzyme and the analysis of the key features in the catalytic site are also described. Furthermore, the ability of pyrazolotriazinones to cross the blood–brain barrier (BBB) was evaluated by passive diffusion and those who showed great GSK-3 inhibition and permeation to the central nervous system (CNS) showed neuroprotective properties against tau hyperphosphorylation in a cell-based model. These new brain permeable pyrazolotriazinones may be used for key in vivo studies and may be considered as new leads for further optimisation for the treatment of AD.

Synthesis, in vitro and in vivo anticancer activity of novel 1-(4-imino-1-substituted-1H-pyrazolo[3,4-d]pyrimidin-5(4H)-yl)urea derivatives

A series of pyrazolo[3,4-d]pyrimidine and urea hybrids have been designed, synthesized and evaluated for their anticancer activity in vitro and in vivo cancer models. Among them, compounds 28, 30, 33, 36 and 37 showed promising cytotoxicity against tested cancer cell lines. Compound 37 (CBS-1) appeared as the most active derivative and it exhibited better cytotoxicity against all tested cell lines as compared to doxorubicin. CBS-1 successfully inhibited cell cycle progression and displayed good apoptosis in A549 cells. CBS-1 significantly induced caspase-3 activation and suppressed NF-κB and IL-6 activation in immunocytochemistry, qPCR and western blot analysis. Additionally, CBS-1 prominently displayed tumoricidal effects in lung adenocarcinoma in vivo xenograft nude mice model.