5394-41-2

Basic information

• Product Name: 5-AMINO-1-(4-NITROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE
• Synonyms: 5-AMINO-1-(4-NITROPHENYL)PYRAZOLE-4-CARBONITRILE;5-AMINO-1-(4-NITROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE;BUTTPARK 51\09-67;3-AMINO-4-CYANO-1-(4-NITROPHENYL)PYRAZOLE;5-azanyl-1-(4-nitrophenyl)pyrazole-4-carbonitrile
• CAS NO: 5394-41-2
• Molecular Formula: C₁₀H₇N₅O₂
• Molecular Weight: 229.19
• Mol File: 5394-41-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 191-193
• Boiling Point: 492.3 °C at 760 mmHg
• Flash Point: 251.5 °C
• Appearance: /
• Density: 1.51 g/cm³
• Vapor Pressure: 7.8E-10mmHg at 25°C
• Refractive Index: 1.725
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -2.01±0.10(Predicted)
• CAS DataBase Reference: 5-AMINO-1-(4-NITROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1-(4-NITROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(5394-41-2)
• EPA Substance Registry System: 5-AMINO-1-(4-NITROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(5394-41-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 5394-41-2(Hazardous Substances Data)

Usage

General Description

5-Amino-1-(4-nitrophenyl)-1H-pyrazole-4-carbonitrile, also known as CAS number: 1076287-03-1, is an organic compound with a molecular formula of C11H8N6O2. This chemical substance falls under the category of nitrogen-containing heterocyclic compounds, known for their prevalence in biological activities. It appears as a slightly yellowish crystalline solid substance under normal conditions. The nitrophenyl part of its structure suggests that it has potential use in creating chemically active intermediates, but it might need proper handling due to the nitro group's explosive tendencies. Limited data is available about its various properties and potential applications, which signifies that it's largely used for research and development scenarios.

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

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

Downstream Products

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

Relevant articles and documents

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.

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 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.