5394-41-2

Usage

Uses

Used in Chemical Synthesis:
5-Amino-1-(4-nitrophenyl)-1H-pyrazole-4-carbonitrile is used as a chemical intermediate for the synthesis of various compounds. Its nitrophenyl component makes it a candidate for further chemical reactions, potentially leading to the creation of new molecules with specific properties.
Used in Research and Development:
In the field of scientific research, 5-Amino-1-(4-nitrophenyl)-1H-pyrazole-4-carbonitrile is employed as a research compound. Its unique structure and properties are of interest to chemists and biologists, who may investigate its potential interactions with biological systems or its role in chemical processes.
Used in Pharmaceutical Development:
Although data is limited, the compound's presence in the class of nitrogen-containing heterocyclic compounds suggests that it could be used as a starting material in the development of pharmaceuticals. Its potential applications in this industry could include the creation of new drugs or the improvement of existing ones, particularly if its biological activity can be harnessed effectively.
Used in Material Science:
The properties of 5-Amino-1-(4-nitrophenyl)-1H-pyrazole-4-carbonitrile may also be relevant in material science, where it could be explored for its potential to contribute to the development of new materials with specific characteristics, such as improved stability or reactivity.

InChI:InChI=1/C10H7N5O2/c11-5-7-6-13-14(10(7)12)8-1-3-9(4-2-8)15(16)17/h1-4,6H,12H2

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 100-16-3 4-nitrophenylhydrazone 
• 109-77-3 malononitrile 
• 123-06-8 Ethoxymethylenemalononitrile 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 65973-73-1 4-Amino-1-(4-nitrophenyl)-1H-pyrazolo<3,4-d>pyrimidin 
• 135108-62-2 4-Amino-5-methyl-1-(4-nitro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 16459-44-2 1-(4-nitrophenyl)-1H-pyrazol-5-amine 
• 77746-76-0 N,N-Dimethyl-N'-[2-(4-nitro-phenyl)-2H-pyrazol-3-yl]-formamidine 
• 77746-59-9 N'-[4-Formyl-2-(4-nitro-phenyl)-2H-pyrazol-3-yl]-N,N-dimethyl-formamidine 
• 77746-86-2 N-[2-(4-Nitro-phenyl)-2H-pyrazol-3-yl]-acetamide 
• 1269662-47-6 ethyl 4-amino-6-methyl-1-(4-nitrophenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 1269662-40-9 methyl 4-amino-6-methyl-1-(4-nitrophenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 1301185-11-4 1-(4-nitrophenyl)-1H-pyrazole-4-carboximidamide 
• 102539-56-0 1-p-nitrophenylpyrazole-4-carbonitrile 
• 135108-77-9 4-Amino-1-(4-amino-phenyl)-5-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 

Relevant academic research and scientific papers

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.

Design, synthesis and insecticidal activities of N-(4-cyano-1-phenyl-1H-pyrazol-5-yl)-1,3-diphenyl-1H-pyrazole-4-carboxamide derivatives

Insect ryanodine receptor is one of the promising targets for the development of novel insecticides. In order to search for potent insecticides targeting the ryanodine receptor (RyR), a series of novel diphenyl-1H-pyrazole derivatives with cyano substituent were designed and synthesized. Their insecticidal activities against diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to high activities at the four concentrations. Among these compounds, N-(4-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)-3-phenyl-1H-pyrazole-4-carboxamide (5g) showed 84% larvicidal activity against Plutella xylostella at the concentration of 0.1 mg L-1. Molecular docking showed the predicted binding mode between 5g and protein receptor, which could suggest that the title compounds were the possible activators of insect RyR.

GLUCOSE TRANSPORT INHIBITORS

The present invention relates to chemical compounds of general formula (I): in which RA, RB, RC, RD, m, and n are as given in the description and in the claims, and which effectively and selectively inhibit glucose transporter 1 (GLUT1), to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, as well as to intermediate compounds useful in the preparation of said compounds.

Synthesis and antileishmanial activity of new 1-aryl-1H-pyrazole-4- carboximidamides derivatives

Chemotherapy for leishmaniasis, diseases caused by protozoa of the genus Leishmania, remains inefficient in several treatments. So there is a need to search for new drugs. In this work, we have synthesized 1-aryl-1H-pyrazole-4- carboximidamides derivatives and evaluated antileishmanial activities in vitro, as well as cytotoxic effects. Structure-activity relationship (SAR) studies were carried out with all the compounds of the series. Compound 2 showed an activity profile that can be improved through medicinal chemistry strategies.

Synthesis of N-aryl-5-amino-4-cyanopyrazole derivatives as potent xanthine oxidase inhibitors

Some pyrazolo[3,4-d]pyrimidines, structurally related with allopurinol, a well known xanthine oxidase inhibitor, clinically used in the therapy of gout, have also been reported as potent inhibitors of xanthine oxidase and the growth of several human tumour cell lines. Considering the potential interest of this family of compounds, the aim of the present study was to synthesise and provide a full chemical characterization of new N-aryl-5-amino-4-cyanopyrazole derivatives and their corresponding pyrazolo[3,4-d]pyrimidines. Their biological activity pertaining to the xanthine oxidase inhibition and effect on the growth of three tumour cell lines (MCF-7, NCI-H460, and SF-268) are also provided. With only one exception, the synthesised compounds showed no effect on the growth of the three tumour cell lines. However, a strong xanthine oxidase inhibitory activity was observed for almost all pyrazolo[3,4-d]pyrimidines tested, revealing some of them IC50 values below 1 μM. The results of the molecular docking studies of these compounds, against xanthine oxidoreductase are also described, providing an atomistic explanation of the differences in the inhibitory efficiency. MEP calculations were used to explain different inhibitory efficiency of similar inhibitors.

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.

Synthesis and adenosine receptor affinity of a series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine

Pyrazolo[3,4-d]pyrimidines are pyrazolo analogues of purines. They have been shown to be a general class of compounds which exhibit A1 adenosine receptor affinity. Two series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine have been synthesized. The first involved substitution of the N1-position while the second involved substitution of the N5-position. Both alkyl and aryl substituents were examined. All compounds were tested for A1 adenosine receptor affinity by using a (R)-[3H]-N6-(phenylisopropyl)adenosine binding assay. The 3-chlorophenyl group showed the greatest activity in the N1-position and the butyl group produced the greatest activity in the N5-position. Combination of the best substituent in each of these positions enhanced the overall activity. The most potent compound was 4-amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one with an IC50 of 6.4 X 10-6 M. Selectivity at the receptor subclasses was examined by performing an A2 adenosine receptor affinity assay with [3H]CGS 21680. This series of compounds were slightly less potent at A2 receptors. 4-Amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one was the most potent compound with an IC50 of 19.2 X 10-6 M.