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Usage

Uses

Used in Pharmaceutical Industry:
5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carbonitrile is used as a potential therapeutic agent for drug development due to its unique chemical structure and potential pharmaceutical properties. Further research and studies are required to explore its specific applications and efficacy in treating various medical conditions.
Used in Research and Development:
In the field of chemical research and development, 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carbonitrile serves as a valuable compound for studying the properties and behavior of pyrazole-based organic compounds. Its unique structure allows researchers to investigate its reactivity, stability, and potential interactions with other molecules, contributing to the advancement of organic chemistry and related fields.

Upstream product

• 4930-98-7 pyrid-2-ylhydrazine 
• 123-06-8 Ethoxymethylenemalononitrile 

Downstream Products

• 1186658-01-4 C₂₆H₁₉N₉O₃ 
• 1186658-09-2 C₁₉H₁₄N₈O 
• 650637-99-3 4-chloro-1-(pyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidine 

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.

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.

AZO PIGMENT, PIGMENT DISPERSION CONTAINING THE AZO PIGMENT, AND COLORING COMPOSITION

Provided is an azo pigment having excellent coloring characteristics such as high tinctorial strength and hue and having excellent durability such as high resistance to light and ozone, a pigment dispersion containing the azo pigment, and a coloring composition. An azo pigment represented by the following general formula (1), a tautomer of the azo pigment, and a salt or a hydrate thereof: (In the general formula (1), G0 and G1 each independently represents a non-metal atomic group which can form a 5- or 6-membered heterocyclic ring wherein each heterocyclic ring may be unsubstituted or may have a substituent; each heterocyclic ring may be a monocyclic ring or a condensed ring; X represents a hetero atom; n represents an integer of 1 to 4; when n = 2, the compound of formula (1) represents a dimer formed via A or a heterocyclic group represented by G0 or G1;. when n = 3, the compound of formula (1) represents a trimer formed via A and/or a heterocyclic group represented by G0 or C1; when n = 4, the compound of formula (1) represents a tetramer formed via A and/or a heterocyclic group represented by G0 or G1; A represents any one selected from the group of the specific substituents.)

Flow and batch mode focused microwave synthesis of 5-amino-4-cyanopyrazoles and their further conversion to 4-aminopyrazolopyrimidines

A new approach to the synthesis of 5-amino-4-cyanopyrazoles has been developed, utilising a novel flow microwave device. These products are then converted by a batch mode microwave process to structurally more complex dimeric and 'mixed' pyrazolopyrimidine structures. The Royal Society of Chemistry.

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.

PYRAZOLOPYRIMIDINES AS KINASE INHIBITORS

The present invention relates generally to inhibitors of the kinases and more particularly to novel pyrazolopyrimidine compounds.

Novel pyrazolopyrimidine derivatives as GSK-3 inhibitors

A series of [1-aryl-1H-pyrazolo[3,4-d]pyrimidin-4-yl]arylhydrazones were discovered as novel inhibitors glycogen synthase kinase-3 (GSK-3). Based on initial modeling a detailed SAR was constructed. Modification of the interior binding aryl ring (Ar1) determined this to be a tight binding region with little room for modification. As predicted from the model, a large variety of modifications could be incorporated into the hydrazone aryl ring. This work led to GSK-3 inhibitors in the low nano-molar range.