3656-04-0

Usage

Physical state

Bright orange, crystalline substance

Uses

pH indicator with a transition range of 3.2 4.4, detecting copper and zinc ions in solutions, potential applications in medicine and cancer research

Azo group

Allows for intense absorption in the visible region, useful for colorimetric assays and tests

Molecular structure

Contains a pyrazole ring with two amino groups (-NH2) at the 3 and 5 positions, an azo group (-N=N-) connecting a 4-chlorophenyl group to the pyrazole ring.

Upstream product

• 882-32-6 p-chlorophenylazomalononitrile 
• 106-47-8 4-chloro-aniline 
• 109-77-3 malononitrile 
• 302-01-2 hydrazine 
• 946-76-9 2-[(4-chlorophenyl)hydrazono]malononitrile 

Downstream Products

• 114275-67-1 2-Amino-3-(4-chloro-phenylazo)-5-methyl-pyrazolo[1,5-a]pyrimidin-7-ol 
• 114275-47-7 7-Amino-9-(4-chloro-phenylazo)-1,3,4,5-tetrahydro-1,4a,4b,8-tetraaza-fluoren-2-one 
• 121580-43-6 3,5-diamino-4-(p-chlorophenylazo)-1-<α-phenylhydrazono-α-(acetyl)methyl>pyrazole 
• 114275-64-8 3-(4-Chloro-phenylazo)-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-2-ylamine 
• 134045-63-9 3-(4-Chloro-phenylazo)-5,7-diphenyl-pyrazolo[1,5-a]pyrimidin-2-ylamine 
• 114275-70-6 4,7-Diamino-8-(4-chloro-phenylazo)-pyrazolo[5,1-c][1,2,4]triazine-3-carbonitrile 
• 114275-62-6 2-Amino-3-(4-chloro-phenylazo)-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-6-carbonitrile 
• 114275-59-1 2,7-Diamino-3-(4-chloro-phenylazo)-pyrazolo[1,5-a]pyrimidine-6-carbonitrile 
• 135085-18-6 2,5-diamino-6,7-dicyano-3-(p-chlorophenylazo)pyrazolo<1,5-a>pyrimidine 
• 155375-42-1 2,5-diamino-3-((4-chlorophenyl)diazenyl)-7-(methylthio)pyrazolo[1,5-a]pyrimidine-6-carbonitrile 
• 155375-53-4 2-Amino-3-(4-chloro-phenylazo)-5-hydroxy-7-methylsulfanyl-pyrazolo[1,5-a]pyrimidine-6-carbonitrile 
• 114275-56-8 2,5-Diamino-3-(4-chloro-phenylazo)-7-(4-methoxy-phenyl)-pyrazolo[1,5-a]pyrimidine-6-carbonitrile 
• 114275-50-2 2,5-Diamino-3-(4-chloro-phenylazo)-7-phenyl-pyrazolo[1,5-a]pyrimidine-6-carbonitrile 
• 114275-53-5 2,5-Diamino-7-(4-chloro-phenyl)-3-(4-chloro-phenylazo)-pyrazolo[1,5-a]pyrimidine-6-carbonitrile 

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 of pyrazolopyrimidine derivatives along with its biological activity including toxicity studies

Pyrazolopyrimidines and related fused heterocycles are of interest as potential bioactive molecules. The heterocyclic fusion of pyrimidine ring and pyrazole ring resulted in formation of pyrazolopyrimidines, the structural analogues of biogenic purine class, undoubtedly, has high significance in the field of pharmaceutical and biotechnological sciences with wide spectrum of biological activities and its several derivatives. Toxicity may be due to the accumulation in a specific organ/ tissue (e.g. bosentan), the co - administration of other drugs affecting ADMET (absorption, distribution, metabolism, elimination and toxicity) Cmax reaching off target IC50, or the high Cmax required for therapeutic effects. Assessing the relative drug efficacy and toxicity is important for medicinal chemists, pharmacologists, pharmacists, physicians. As multiple treatment options are available for many diseases, relative toxicity assessment is necessary. Difficulty in direct clinical trial comparisons forces network meta-analyses for estimating the relative toxicity. Therapeutic index (TI) assumes simplified linear relationships between receptor affinity, maximum unbound plasma drug concentration (Cmax) and toxicity. But high TI does not guarantee safety. For drugs metabolized by cytochrome P450 (CYP450),estimating TI based on target potencies alone is insufficient.

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.

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.

Synthesis, structure characterization and antimicrobial evaluation of 4-(substituted phenylazo)-3,5-diacetamido-1H-pyrazoles

The present article deals with the synthesis, spectral characterization and antimicrobial activity of phenylazo dyes. All of the synthesized phenylazo dyes were characterized using ATR-FTIR, FT-Raman, 1H NMR, 13C NMR, elemental analy

An ecofriendly synthesis and DNA binding interaction study of some pyrazolo [1,5-a]pyrimidines derivatives

The DNA molecule is a target for plethora of anticancer and antiviral drugs that forms covalent and non-covalent adducts with major or minor groove of DNA. In present study we synthesized series of novel Pyrazolo [1,5-a]pyrimidine derivatives. The newly s

Studies on 3,5-Diaminopyrazoles: New Routes for the Synthesis of New Pyrazoloazines and Pyrazoloazoles

The reactions of 3,5-diaminopyrazoles with α,β-unsaturated nitriles, active methylene reagents and nitrile imines are described.The investigations make several new pyrazoloazines and pyrazoloazoles accessible.