135108-48-4

Basic information

• Product Name: 5-AMINO-1-(2-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE
• Synonyms: BUTTPARK 51\09-69;AKOS B029475;5-AMINO-1-(2-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE
• CAS NO: 135108-48-4
• Molecular Formula: C₁₀H₇FN₄
• Molecular Weight: 202.19
• Mol File: 135108-48-4.mol

Chemical Properties

• Melting Point: 145.9-146.8 °C(Solv: ethanol (64-17-5))
• Boiling Point: 402.429 °C at 760 mmHg
• Flash Point: 197.182 °C
• Appearance: /
• Density: 1.36
• Storage Temp.: 2-8°C
• PKA: -1.53±0.10(Predicted)
• CAS DataBase Reference: 5-AMINO-1-(2-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1-(2-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(135108-48-4)
• EPA Substance Registry System: 5-AMINO-1-(2-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(135108-48-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 135108-48-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Amino-1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile is used as a key intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Amino-1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile serves as an intermediate in the production of agrochemicals, aiding in the creation of effective pesticides and other agricultural products.
Used in Biological Research:
5-Amino-1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile is utilized in biological research as a compound with potential anti-inflammatory and anti-cancer properties, providing a foundation for the exploration of new treatments and therapies in medicine.
Used in Drug Development:
As a compound with demonstrated biological activities, 5-Amino-1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile is used in drug development for its potential to contribute to the creation of novel pharmaceuticals with specific therapeutic targets.

Upstream product

• 2924-15-4 (2-fluorophenyl)hydrazine hydrochloride 
• 123-06-8 Ethoxymethylenemalononitrile 
• 348-54-9 2-Fluoroaniline 
• 2368-80-1 2-fluorophenylhydrazine 
• 122-51-0 orthoformic acid triethyl ester 
• 109-77-3 malononitrile 

Downstream Products

• 1242015-26-4 1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile 
• 1269291-92-0 5-chloro-1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile 
• 1293979-10-8 7-(2-fluorophenyl)-3H-pyrazolo[3,4-d][1,2,3]triazin-4(7H)-one 
• 630107-83-4 4-chloro-1-(2-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidine 
• 1431459-38-9 5-[1-(2-fluorophenyl)-1H-pyrazole-4-yl]-1H-tetrazole 
• 630107-81-2 5-amino-1-(2-fluorophenyl)-1H-pyrazole-4-carboxamide 
• 135108-57-5 4-Amino-1-(2-fluoro-phenyl)-5-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 

Relevant articles and documents

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.

Thermal Ring-Opening of Pyrazolo[3,4-d][1,2,3]triazin-4-ones: An Experimental and Theoretical Study

Several 3-pyrazolylcarbonyl-pyrazolo[3,4-d][1,2,3]triazin-4-ones have been prepared from 5-amino-1H-pyrazole-4-carbonitriles through a simple sequence. In the first step, diazotization of the corresponding aminopyrazoles afforded pyrazolo[3,4-d][1,2,3]triazin-4-ones. Next, thermal rearrangement of these compounds through nitrogen elimination gave the final products. The proposed mechanism for the ring-opening of the pyrazolotriazinones to give the pyrazolylcarbonyl-pyrazolotriazinones involves the generation of an iminoketene intermediate, which reacts with a second molecule of pyrazolotriazinone. The complete mechanism of product formation involving the iminoketene intermediate, and all other reasonable pathways, have been explored in detail through DFT calculations. Furthermore, additional experiments to corroborate the presence of the iminoketene intermediate were carried out.

Identification of novel GLUT inhibitors

The compound class of 1H-pyrazolo[3,4-d]pyrimidines was identified using HTS as very potent inhibitors of facilitated glucose transporter 1 (GLUT1). Extensive structure–activity relationship studies (SAR) of each ring system of the molecular framework was established revealing essential structural motives (i.e., ortho-methoxy substituted benzene, piperazine and pyrimidine). The selectivity against GLUT2 was excellent and initial in vitro and in vivo pharmacokinetic (PK) studies are encouraging.

Effectiveness of novel 5-(5-amino-1-aryl-1H-pyrazol-4-yl)-1H-tetrazole derivatives against promastigotes and amastigotes of leishmania amazonensis

In this research, a series of substituted 5-(5-amino-1-aryl-1H-pyrazol-4- yl)-1H-tetrazoles were synthesized and evaluated for in vitro antileishmanial activity. Among the derivatives, examined compounds 3b and 3l exhibited promising activity against promastigotes and amastigotes forms of Leishmania amazonensis. The cytotoxicity of these compounds was evaluated on murine cells, giving access to the corresponding selectivity index (SI).

An efficient synthesis of new 5-(1-Aryl-1H-pyrazole-4-yl)-1H-tetrazoles from 1-Aryl-1H-pyrazole-4-carbonitriles via [3 + 2] cycloaddition reaction

A series of new 5-(1-aryl-1H-pyrazole-4-yl)-1H-tetrazoles 4a-l were synthesized via [3 + 2] cycloaddition reaction from 1-aryl-1H-pyrazole-4- carbonitriles 3a-l, sodium azide and ammonium chloride, using dimethylformamide (DMF) as solvent, in good yields: 64-85%. The structures of these newly synthesized compounds were determined from the IR, 1H- and 13C-NMR spectroscopic data and elemental analyses.

New application of heterocyclic diazonium salts. Synthesis of pyrazolo[3,4-d][1,2,3]triazin-4-ones and imidazo[4,5-d][1,2,3]triazin-4-ones

The pyrazolo[3,4-d][1,2,3]triazin-4-ones 3 and imidazo[4,5-d][1,2,3] triazin-4-ones 4 are analogs structurally related to purines that have showed a wide and significant variety of biological activity. These compounds were synthesized by one-pot diazotization of 5-amino-1H-pyrazole-4-carbonitriles 1 and 5-amino-1H-imidazole-4-carbonitriles 2, respectively.

Discovery and evaluation of 7- lkyl-1,5-bis-aryl-pyrazolopyridinones as Highly potent, selective, and orally efficacious inhibitors of p38α mitogen-activated protein kinase

The p38α mitogen-activated protein (MAP) kinase is a central signaling molecule in many proinflammatory pathways, regulating the cellular response to a multitude of external stimuli including heat, ultraviolet radiation, osmotic shock, and a variety of cytokines especially interleukin-1- and tumor necrosis factor α. Thus, inhibitors of this enzyme are postulated to have significant therapeutic potential for the treatment of rheumatoid arthritis, inflammatory bowel disease, and Crohn's disease, as well as other diseases where aberrant cytokine signaling is the driver of disease. In this communication, we describe a novel class of 7-alkyl-1,5-bis-aryl- pyrazolopyridinone-based p38α inhibitors. In particular, compound 3f is highly potent in the enzyme and cell-based assays, selective in an Ambit kinase screen, and efficacious (ED50 - 0.01 mg/kg) in the rat collagen induced arthritis (CIA) model.

6-Arylmethyl-substituted pyrazolopyrimidines

The invention relates to novel 6-arylmethyl-substituted pyrazolopyrimidines, process for their preparation and their use for producing medicaments for improving perception, concentration, learning and/or memory.

6-ARYLMETHYL-SUBSTITUTED PYRAZOLOPYRIMIDINES

The invention relates to novel 6-arylmethyl-substituted pyrazolopyrimidines of formula (I) wherein R1 represents phenyl, pyridyl or thiophenyl, and R2 represents phenyl or heteroaryl. The invention also relates to the salts and solvates thereof, and/or solvates of the salts thereof, to methods for producing said pyrazolopyrimidines, and to the use of the same for producing pharmaceuticals for improving perception, power of concentration, learning capacity and/or memory retention.

6-CYCLYLMETHYL- AND 6-ALKYLMETHYL-SUBSTITUTED PYRAZOLOPYRIMIDINES

The invention relates to novel 6-cyclylmethyl- and 6-alkylmethyl-substituted pyrazolopyrimidines, method for production and use thereof for the production of medicaments for the improvement of cognition, concentration, learning and/or memory capacity.