51516-71-3

Usage

Uses

Used in Pharmaceutical Industry:
5-Amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile is used as a key intermediate in the synthesis of various pharmaceuticals for its potential to contribute to the development of new drugs with unique therapeutic properties. Its presence in the molecular structure can influence the pharmacokinetics and pharmacodynamics of the final drug product.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile is utilized as a precursor in the creation of novel agrochemicals, potentially leading to the development of more effective pesticides, herbicides, or other crop protection agents.
Used in Drug Discovery and Development:
5-Amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile is employed as a chemical probe in drug discovery processes, aiding researchers in identifying new molecular targets and pathways for therapeutic intervention. Its unique structural features can be leveraged to design compounds with enhanced biological activity and selectivity.
Used in Chemical Research:
5-Amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile is also used in academic and industrial chemical research settings as a model compound to study the reactivity and properties of pyrazole derivatives and carbonitrile-containing molecules, which can provide insights into the design of new chemical entities with specific applications.

Upstream product

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

Downstream Products

• 135108-58-6 4-Amino-1-(3-fluoro-phenyl)-5-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 864871-85-2 1-(3-fluoro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one 
• 50427-74-2 5-amino-1-(3-fluoro-phenyl)-1H-pyrazole-4-carboxylic acid amide 
• 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 
• 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 

Relevant academic research and scientific papers

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.

A Convenient Synthesis of Pyrazole-imidazoline Derivatives by Microwave Irradiation

A series of 28 hybrids pyrazole-imidazolines 1a–n and 2a–n were synthesized by a new methodology using microwave irradiation, in short time (20–30?min), in low power (50–70?W), and in 34–92% yield. Among all methodologies evaluated, no side products were obtained. All derivatives were completely characterized by FT–IR, 1H and 13C NMR, GC–MS, and HRMS.

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.

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.

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).

Synthesis and antileishmanial evaluation of 1-aryl-4-(4,5-dihydro-1H- imidazol-2-yl)-1H-pyrazole derivatives

A series of 1-aryl-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazoles (4a-g) and 5-amino-1-aryl-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazoles (5a-g) were synthesized and evaluated in vitro against three Leishmania species: L. amazonensis, L. braziliensis and L. infantum (L. chagasi syn.). The cytotoxicity was assessed. Among the derivatives examined, six compounds emerged as the most active on promastigotes forms of L. amazonensis with IC50 values ranging from 15 to 60 μM. The reference drug pentamidine presented IC 50 = 10 μM. However, these new compounds were less cytotoxic than pentamidine. Based on these results, the more promising derivative 5d was tested further in vivo. This compound showed inhibition of the progression of cutaneous lesions in CBA mice infected with L. amazonensis relative to an untreated control.

1, 5-DIHYDRO-PYRAZOLO (3, 4-D) PYRIMIDIN-4-ONE DERIVATIVES AND THEIR USE AS PDE9A MODULATORS FOR THE TEATMENT OF CNS DISORDERS

The invention relates to novel substituted pyrazolopyrimidines. Chemically, the compounds are characterised by general Formula (I): with R1 being phenyl or pyridyl, any of which is substituted with 1 to 4, preferably 1 to 3 substituents X; X in

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.