91091-13-3

Usage

Uses

Used in Pharmaceutical Synthesis:
5-AMINO-1-BENZYL-1H-PYRAZOLE-4-CARBONITRILE is used as a key intermediate for the synthesis of various pharmaceutical compounds and organic products. Its unique structure and functional groups contribute to the development of new drugs and therapeutic agents.
Used in Medicinal Research:
In the field of medicinal research, 5-AMINO-1-BENZYL-1H-PYRAZOLE-4-CARBONITRILE is utilized as a building block in the synthesis of heterocyclic compounds and pharmaceutical agents. Its versatile reactivity allows for the creation of novel molecules with potential therapeutic properties.
Used in Chemical Research:
5-AMINO-1-BENZYL-1H-PYRAZOLE-4-CARBONITRILE is also employed in chemical research for its potential applications in the development of new organic products and materials. Its unique structure and functional groups enable the exploration of new chemical reactions and synthesis pathways.
Used in Drug Development:
5-AMINO-1-BENZYL-1H-PYRAZOLE-4-CARBONITRILE is used as a starting material in drug development, where its reactivity and structural features can be leveraged to design and synthesize new pharmaceutical agents with improved efficacy and selectivity.
Used in Organic Chemistry:
In the realm of organic chemistry, 5-AMINO-1-BENZYL-1H-PYRAZOLE-4-CARBONITRILE serves as a valuable compound for studying and understanding various chemical reactions and mechanisms. Its presence in the synthesis of heterocyclic compounds and pharmaceutical agents highlights its importance in advancing the field of organic chemistry.

Upstream product

• 123-06-8 Ethoxymethylenemalononitrile 
• 555-96-4 Benzylhydrazine 
• 100-44-7 benzyl chloride 
• 16617-46-2 3-amino-4-cyano-2H-pyrazole 
• 20570-96-1 benzylhydrazine dihydrochloride 

Downstream Products

• 56156-22-0 5-amino-1-benzyl-1H-pyrazole-4-carboxylic acid amide 
• 99196-35-7 1-Benzyl-4-cyano-5-<(3-oxo-1-cyclohexen-1-yl)amino>pyrazole 
• 5444-61-1 1-benzyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine 
• 821004-24-4 5-amino-1-benzylpyrazole-4-carboxamidoxime 
• 50270-30-9 1-benzyl-4,6-dichloropyrazolo[3,4-d]pyrimidine 
• 99162-91-1 4-Amino-1-benzyl-7,8-dihydro-6H-pyrazolo<3,4-b>quinolin-5-one 
• 137278-90-1 4-Amino-1-benzyl-5,6,7,8-tetrahydropyrazolo<3,4-b>quinolin-5-ol 
• 121358-86-9 1-benzyl-1H-pyrazole-4-carbonitrile 
• 1050619-95-8 8H-pyrazolo[5,1-a]isoindole-3-carbonitrile 
• 1050619-85-6 1-benzyl-5-chloro-1H-pyrazole-4-carbonitrile 
• 1050619-79-8 10H-pyrazolo[5,1-c][1,2,4]benzotriazepine-3-carbonitrile 
• 1050619-74-3 7-benzyl-3,7-dihydro-4H-pyrazolo[3,4-d][1,2,3]triazin-4-one 
• 128691-35-0 3-Amino-1-benzylpyrazol-4-carbonsaeureamid 
• 1361961-33-2 1-benzyl-6-(difluro-(4-fluorophenyl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol 

Relevant academic research and scientific papers

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.

AZOLOPYRIDINE AND AZOLOPYRIMIDINE COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are azolopyridine and azolopyrimidine compounds for treatment of JAK kinase mediated diseases, including JAK2 kinase-, JAK3 kinase- or TYK2 kinase-mediated diseases. Also provided are pharmaceutical compositions comprising the compounds and methods of using the compounds and compositions.

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.

New application of heterocyclic diazonium salts: Synthesis of new pyrazolo[3,4-d][1,2,3]triazin-4-ones

7-Substituted 3,7-dihydro-4H-pyrazolo[3,4-d][1,2,3]triazin-4-ones 2a-d were conveniently prepared by direct diazotization of 5-aminopyrazole-4- carbonitriles 1a-d in HCl media. Different reaction conditions and the effects of substituents on N-1 of the pyrazole ring were studied. A possible mechanistic exlpanation of the observed process is proposed. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Acetonitrile-mediated synthesis of 2,4-dichloroquinoline from 2-ethynylaniline and 2,4-dichloroquinazoline from anthranilonitrile

2,4-Dichloroquinolines and 2,4-dichloroquinazolines were synthesized from 2-ethynylanilines and anthranilonitriles, respectively, using diphosgene in acetonitrile and heating at 130 °C or 150 °C for 12 hours. This reaction was applied to the synthesis of 4,6-dichloropyrazolo[3,4-d]pyrimidine (dichloro-9H-isopurine). The postulated mechanism is also described. Georg Thieme Verlag Stuttgart.

Synthesis and anticonvulsant activity of N-benzylpyrrolo[2,3-d]-, - pyrazolo[3,4-d]-, and -triazolo[4,5-d]pyrimidines: Imidazole ring-modified analogues of 9-(2-fluorobenzyl)-6-(methylamino)-9H-purine

Analogues of 9-(2-fluorobenzyl)-6-(methylamino)-9H-purine (1) containing isosteric replacements of the imidazole ring atoms were synthesized and tested for anticonvulsant activity. The pyrrolo[2,3-d]-, pyrazolo[a,4-d]-, and triazolo[4,5-d]pyrimidines were less active than 1 against maximal electroshock-induced seizures (MES) in rats when given po. The differences in anti-MES activity for these analogues was not explained by differences in pK(a) or lipophilicity. However, the four classes of heterocycles have distinctly different calculated electrostatic isopotential maps, which may be related to optimum anticonvulsant activity.

Pyrazolopyridine cycloalkanones and process for their preparation

Novel tetrahydropyrazolo-[3,4-b]quinolinones, cyclopenta[b]pyrazolo-[4,3-e]pyridinones and cyclohepta[b]-pyrazolo[4,3-e]pyridinones, useful as anxiolytics having reduced side effects, are disclosed, including methods of preparation, pharmaceutical compositions containing them and intermediates used in their preparation.