140651-18-9

Usage

Uses

Used in Chemical Research:
Phenol, 4-[(3,5-diamino-1H-pyrazol-4-yl)azo]is utilized as a reagent in laboratory experiments and chemical research, serving as a valuable tool for understanding its properties and potential applications.
Used in Dye and Pigment Production:
Due to its azo dye group, Phenol, 4-[(3,5-diamino-1H-pyrazol-4-yl)azo]is used as a component in the production of dyes and pigments, contributing to the coloration and stability of these products.
Used in Pharmaceutical and Medical Research:
Phenol, 4-[(3,5-diamino-1H-pyrazol-4-yl)azo]-'s structure suggests that it may possess biological activities, making it a subject of interest for pharmaceutical and medical research. Its potential in this field is currently under investigation.
Used in Industrial Applications:
Phenol, 4-[(3,5-diamino-1H-pyrazol-4-yl)azo]is used in various industrial applications, where its color and stability properties are beneficial. The specific industries and applications may vary, and further research is needed to fully understand its potential in these areas.

Upstream product

• 123-30-8 4-amino-phenol 

Downstream Products

• 1649984-30-4 2-amino-3-[(E)-(4-hydroxyphenyl)diazenyl]-5-(4-methoxyphenyl)-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-31-5 2-amino-3-[(E)-(4-hydroxyphenyl)diazenyl]-5-(2-methoxyphenyl)-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-32-6 2-amino-5-(4-hydroxy-3-methoxyphenyl)-3-[(E)-(4-hydroxyphenyl)diazenyl]-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-33-7 2-amino-5-(2,4-dimethoxyphenyl)-3-[(E)-(4-hydroxyphenyl)diazenyl]-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-34-8 2-amino-5-(2,4,6-trimethoxyphenyl)-3-[(E)-(4-hydroxyphenyl)diazenyl]-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-35-9 2-amino-5-(3-hydroxyphenyl)-3-[(E)-(4-hydroxyphenyl)diazenyl]-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-36-0 2-amino-5-(2,6-dimethylphenyl)-3-[(E)-(4-hydroxyphenyl)diazenyl]-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-37-1 2-amino-5-(2-fluorophenyl)-3-[(E)-(4-hydroxyphenyl)diazenyl]-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-38-2 2-amino-5-(3-fluorophenyl)-3-[(E)-(4-hydroxyphenyl)diazenyl]-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-39-3 2-amino-5-(4-fluorophenyl)-3-[(E)-(4-hydroxyphenyl)diazenyl]-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-40-6 2-amino-5-(2-chloro-6-fluorophenyl)-3-[(E)-(4-hydroxyphenyl)diazenyl]-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-41-7 2-amino-5-(2,6-dichlorophenyl)-3-[(E)-(4-hydroxyphenyl)diazenyl]-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-42-8 2-amino-3-[(E)-(4-hydroxyphenyl)diazenyl]-5-[2-(trifluoromethyl)phenyl]-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1649984-44-0 2-amino-3-[(E)-(4-hydroxyphenyl)diazenyl]-5-[4-(trifluoromethyl)phenyl]-5,6-dihydropyrazolo[1,5-a]pyrimidin-7(4H)-one 

Relevant academic research and scientific papers

A facile synthesis of new monoazo disperse dyes derived from 4-hydroxyphenylazopyrazole-5-Amines: Evaluation of microwave assisted dyeing behavior

A series of new monoazo disperse dyes containing pyrazolopyrimidine moieties was synthesized by coupling malononitrile or 3-Aminocrotononitrile with 4-hydroxybenzenediazonium chloride. Treatment of the resulting products with hydrazine hydrate yields the corresponding 4-Arylazoaminopyrazoles, which then react with either 2,4-pentanedione and enaminonitriles or aryl-substituted enaminoketones to give the target pyrazolopyrimidine monoazo disperse dyes. Structural assignments of the dyes were made using both NMR spectroscopic and X-ray crystallographic methods. A high temperature dyeing method, by microwave irradiation, was employed with polyester fabrics. Most of the dyed fabrics tested displayed moderate light fastness and excellent washing and perspiration fastness levels.

Design, synthesis, molecular modeling, and antimicrobial potential of novel 3-[(1H-pyrazol-3-yl)imino]indolin-2-one derivatives as DNA gyrase inhibitors

A series of 3-[(1H-pyrazol-3-yl)imino]indolin-2-one derivatives were designed using the molecular hybridization method, characterized using different spectroscopic techniques, and evaluated for their in vitro antimicrobial activity. Most of the target compounds demonstrated good to moderate antimicrobial activity compared with ciprofloxacin and fluconazole. Four compounds (8b, 9a, 9c, and 10a) showed encouraging results, with minimal inhibitory concentration (MIC) values (53.45–258.32 μM) comparable to those of norfloxacin (100.31–200.63 μM) and ciprofloxacin (48.33–96.68 μM). Noticeably, the four derivatives revealed excellent bactericidal and fungicidal activities, except for the bacteriostatic potential of compounds 8b and 9a against Escherichia coli and Staphylococcus aureus, respectively. The time-killing kinetic study against S. aureus confirmed the efficacy of these derivatives. Furthermore, two of the four promising derivatives, 9a and 10a, could prevent the formation of biofilms of S. aureus without affecting the bacterial growth at low concentrations. A combination study with seven commercial antibiotics against the multidrug-resistant bacterium P. aeruginosa showed a notable reduction in the antibiotic MIC values, represented mainly through a synergistic or additive effect. The enzymatic assay implied that the most active derivatives had inhibition potency against DNA gyrase comparable to that of ciprofloxacin. Molecular docking and density functional theory calculations were performed to explore the binding mode and study the reactivity of the promising compounds.

Modification of boc-protected CAN508 via acylation and suzuki-miyaura coupling

The cyclin-dependent kinase inhibitor, CAN508, was protected with di-tert-butyl dicarbonate to access the amino-benzoylated pyrazoles. The bromo derivatives were further arylated by Suzuki-Miyaura coupling using the XPhos Pd G2 pre-catalyst. The coupling

4-Arylazo-3,5-diamino-1H-pyrazole CDK inhibitors: SAR study, crystal structure in complex with CDK2, selectivity, and cellular effects

In a routine screening of our small-molecule compound collection we recently identified 4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of ATP antagonists with moderate potency against CDK2-cyclin E. A preliminary SAR study based on 35 analogues suggests ways in which the pharmacophore could be further optimized, for example, via substitutions in the 4-aryl ring. Enzyme kinetics studies with the lead compound and X-ray crystallography of an inhibitor-CDK2 complex demonstrated that its mode of inhibition is competitive. Functional kinase assays confirmed the selectivity toward CDKs, with a preference for CDK9-cyclin T1. The most potent inhibitor, 4-[(3,5-diamino-1H-pyrazol-4-yl) diazenyl]phenol 31b (CAN508), reduced the frequency of S-phase cells of the cancer cell line HT-29 in antiproliferation assays. Further observed cellular effects included decreased phosphorylation of the retinoblastoma protein and the C-terminal domain of RNA polymerase II, inhibition of mRNA synthesis, and induction of the tumor suppressor protein p53, all of which are consistent with inhibition of CDK9.