3656-02-8

Usage

InChI:InChI=1/C9H10N6/c10-8-7(9(11)15-14-8)13-12-6-4-2-1-3-5-6/h1-5,12H,(H4,10,11,13,14,15)

Upstream product

• 6017-21-6 benzeneazomalononitrile 
• 62-53-3 aniline 
• 306-18-3 2-phenylhydrazonomalononitrile 
• 100-34-5 benzene diazonium chloride 

Downstream Products

• 143571-56-6 Acetic acid 2,5-diamino-7,8-dichloro-9a-cyano-9-oxo-3-phenylazo-9,9a-dihydro-pyrazolo[1,5-a]quinazolin-6-yl ester 
• 98056-24-7 2-Amino-5,7-diphenyl-3-phenylazopyrazolo<1,5-a>pyrimidine 
• 130159-76-1 2,7-Diamino-3-phenylazo-pyrazolo[1,5-a]pyrimidine-5,6-dicarbonitrile 
• 135085-16-4 2,5-diamino-6,7-dicyano-3-phenylazopyrazolo<1,5-a>pyrimidine 
• 155375-38-5 2, 5-diamino-7-(methylthio)-3-(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-6-carbonitrile 
• 155375-49-8 2-Amino-5-hydroxy-7-methylsulfanyl-3-phenylazo-pyrazolo[1,5-a]pyrimidine-6-carbonitrile 
• 118481-14-4 2,5-Diamino-7-(4-methoxy-phenyl)-3-phenylazo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-6-carbonitrile 
• 125655-88-1 2,7-diamino-5-phenyl-3-phenylazopyrazolo<1,5-a>pyrimidine-6-carbonitrile 
• 125655-91-6 2-amino-7-hydroxy-5-phenyl-3-phenylazopyrazolo<1,5-a>pyrimidine-6-carbonitrile 
• 134045-59-3 7-Phenyl-3-phenylazo-5-p-tolyl-pyrazolo[1,5-a]pyrimidin-2-ylamine 
• 134045-62-8 5-Phenyl-3-phenylazo-7-p-tolyl-pyrazolo[1,5-a]pyrimidin-2-ylamine 
• 134045-58-2 5-(4-Bromo-phenyl)-7-phenyl-3-phenylazo-pyrazolo[1,5-a]pyrimidin-2-ylamine 
• 134045-61-7 7-(4-Chloro-phenyl)-5-phenyl-3-phenylazo-pyrazolo[1,5-a]pyrimidin-2-ylamine 
• 134045-60-6 5-(4-Methoxy-phenyl)-7-phenyl-3-phenylazo-pyrazolo[1,5-a]pyrimidin-2-ylamine 

Relevant academic research and scientific papers

Novel heterocyclic disazo dyes containing pyrazole and phenylpyrazole. part 1: Synthesis, characterization, solvent polarity and acid-base sensitive characteristics

A series of diazotised aniline and aniline derivative compounds were reacted with solution of malononitrile in pyridine at 0–5 °C were obtained 1a-1m compounds. Then 4-arylazo-3,5-diamino-1H-pyrazole (2a-2m) derivatives were synthesized by coupling arylazo malononitrile compounds with hydrazine. Finally, the synthesized pyrazole derivative 2a-2m compounds were again diazotised. By reacting these diazotised compounds with 3-amino-5?hydroxy-1-phenylpyrazole, the new thirteen heterocyclic disazo dyes (3a-3m) were joined the dye literature and the dye industry. The structures of these newly synthesized compounds were characterized using elemental analysis and spectroscopic methods such as Fourier transform infrared spectroscopy-Attenuated total reflectance (FT-IR-ATR), 1H-Nuclear magnetic resonance (1H NMR) spectroscopy and mass spectroscopy. Then solvatochromic properties and solvent effect in dimethyl sulfoxide, dimethyl formamide, acetonitrile, acetic acid, methanol and chloroform were investigated. In addition, the effects of organic and inorganic acids and bases on the absorption spectra of the compounds and the substituent effect of the phenyl ring-bound groups were investigated.

Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents

Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. in vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34 μM), MAO B (0.26 μM), and AChE (52 μM), while 32 exhibited a lead for selective MAO A (0.12 μM) inhibition coupled to AChE (48 μM) inhibition. Computational analysis revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand molecule and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1–42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1–42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65 μM), making it a potential lead for Alzheimer's disease application.

Fluoride-responsive organogel containing azobenzyl and cholesterol units

In this paper, two new cholesterol-based compounds O1 and O2 were designed and synthesized. The compound O2 could selectively gel in 1,4-dioxane with porous ribbon structure. The aggregation mode of O2 molecules were characterized by SEM, IR, UV-vis and X

Synthesis, absorption properties and biological evaluation of some novel disazo dyes derived from pyrazole derivatives

In this study, 20 novel disazo dyes containing pyrazole derivatives were synthesized by a convenient method. Diazotized aniline and some aniline derivatives were reacted with malononitrile to give 2-arylazomalononitrile derivatives 1(a-e). The synthesized 2-arylazomalononitrile derivatives were reacted with hydrazine and phenyl hydrazine to afford the corresponding 3,5-diamino-4-arylazo-1 H-pyrazole 2(a-e) and 3,5-diamino-4-arylazo-1-phenylpyrazole 3(a-e). Diazotized compounds of 2(a-e)and 3(a-e) reacted with ethylacetoacetate to give 4-arylazo-3-amino-1 H-pyrazole-5-ylazo-ethylacetoacetate 4(a-e) and 4-arylazo-3-amino-1-phenylpyrazole-5-ylazo-ethylacetoacetate 7(ae). The obtained 4(a-e) and 7(a-e) were reacted with hydrazine and phenyl hydrazine to give disazo dyes 5(a-e), 6(a-e), 8(a-e) and 9(a-e), respectively. The synthesized disazo dyes were characterized by spectroscopic techniques as well as elemental analysis. The solvatochromic behaviours of these dyes in various solvents were examined. Acid-base effects on the absorption maxima of the dyes were also reported. Antimicrobial activities of the synthesized novel disazo dyes were investigated.

Studies with enamines: Route to aminoazolopyrimidines and arylazoazolopyrimidines

An easy preparation of enaminonitrile derivatives and their transformation into new substituted azolopyrimidines is described. The one-step transformation was carried out under microwave irradiation and by classical heating methods. The use of microwave i

DFT, FT-IR, FT-Raman and NMR studies of 4-(substituted phenylazo)-3,5- diacetamido-1H-pyrazoles

We present a detailed analysis of the structural and vibrational spectra of some novel azo dyes. 2-(Substituted phenylazo)malononitriles were synthesized by the coupling reaction of the diazonium salts, which were prepared with the use of various aniline

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.