5334-43-0

Usage

Uses

Used in Chemical Research:
5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE is used as a research compound for its chemiluminescence activity, which can be utilized in the development of new chemical reactions and processes.
Used in Pharmaceutical Industry:
5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE is used as a pharmaceutical compound for its antifilarial activity, which can be employed in the development of treatments for filarial diseases, such as lymphatic filariasis and onchocerciasis.
Used in Drug Development:
5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE is used as a drug development compound for its adenosine receptor affinity, which can be leveraged in the creation of new medications targeting adenosine receptors for various therapeutic applications.
Used in Analytical Chemistry:
5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE is used as an analytical reagent in the detection and quantification of specific substances due to its chemiluminescence properties, which can enhance the sensitivity and accuracy of analytical methods.
Used in Material Science:
5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE is used as a material in the development of new compounds and materials with potential applications in various industries, such as electronics, coatings, and plastics, due to its unique chemical properties.

InChI:InChI=1/C10H8N4/c11-6-8-7-13-14(10(8)12)9-4-2-1-3-5-9/h1-5,7H,12H2

Upstream product

• 100-63-0 phenylhydrazine 
• 123-06-8 Ethoxymethylenemalononitrile 
• 106157-80-6 2-Amino-3-(2-ethylbenzimidazol-1-yl)-2-(2-phenyl-1,1-diazanediylmethyl)-2-propenenitrile 
• 59-88-1 phenylhydrazine hydrochloride 
• 86240-43-9 (ethoxymethylene)malononitrile 
• 670-54-2 ethenetetracarbonitrile 
• 10472-09-0 1-Chloro-2,2-dicyanoethylen 
• 122-51-0 orthoformic acid triethyl ester 
• 109-77-3 malononitrile 
• 106157-75-9 3-amino-3-(o-aminoanilino)-2-cyano-2-propenal phenylhydrazone 

Downstream Products

• 62597-88-0 N-(4-cyano-1-phenyl-1H-pyrazol-5-yl)acetamide 
• 5334-30-5 1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 50427-77-5 5-amino-1-phenyl-1H-pyrazole-4-carboxamide 
• 95834-35-8 4-Cyano-1-phenyl-5-(1-pyrryl)pyrazole 
• 135108-69-9 4-Amino-1-phenyl-5-propyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 141212-96-6 4-Imino-1-phenyl-5-p-tolyl-1,4,5,7-tetrahydro-pyrazolo[3,4-d]pyrimidine-6-thione 
• 135108-71-3 4-Amino-1,5-diphenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 141212-95-5 4-imino-1,5-diphenyl-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-d]pyrimidine-6-thione 
• 142893-03-6 1-(4-Cyano-2-phenyl-2H-pyrazol-3-yl)-3-phenyl-thiourea 
• 141212-97-7 5-(4-Chloro-phenyl)-4-imino-1-phenyl-1,4,5,7-tetrahydro-pyrazolo[3,4-d]pyrimidine-6-thione 
• 106368-35-8 N-(4-cyano-1-phenyl-1H-pyrazol-5-yl)-2-oxoglycine ethyl ester 
• 135108-50-8 4-Amino-5-methyl-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 135108-49-5 4-cyano-5-(3-methyl-1-ureido)-1-phenylpyrazole 
• 153931-80-7 dimethyl 4-amino-1-phenyl-1H-pyrazolo<3,4-b>pyridine-5,6-dicarboxylate 

Relevant academic research and scientific papers

A novel synthetic compound (E)-5-((4-oxo-4h-chromen-3-yl)methyleneamino)-1-phenyl-1h-pyrazole-4-carbonitrile inhibits tnfα-induced mmp9 expression via egr-1 downregulation in mda-mb-231 human breast cancer cells

Breast cancer is a common malignancy among women worldwide. Gelatinases such as matrix metallopeptidase 2 (MMP2) and MMP9 play crucial roles in cancer cell migration, invasion, and metastasis. To develop a novel platform compound, we synthesized a flavonoid derivative, (E)-5-((4-oxo-4H-chromen-3-yl)methyleneamino)-1-phenyl-1H-pyrazole-4-carbonitrile (named DK4023) and characterized its inhibitory effects on the motility and MMP2 and MMP9 expression of highly metastatic MDA-MB-231 breast cancer cells. We found that DK4023 inhibited tumor necrosis factor alpha (TNFα)-induced motility and F-actin formation of MDA-MB-231 cells. DK4023 also suppressed the TNFα-induced mRNA expression of MMP9 through the downregulation of the TNFα-extracellular signal-regulated kinase (ERK)/early growth response 1 (EGR-1) signaling axis. These results suggest that DK4023 could serve as a potential platform compound for the development of novel chemopreventive/chemotherapeutic agents against invasive breast cancer.

Anti-inflammatory drug approach: Synthesis and biological evaluation of novel pyrazolo[3,4-d]pyrimidine compounds

In this study, the acid chlorides of pyrazolo[3,4-d]pyrimidine compounds were prepared and reacted with a number of nucleophiles. The novel compounds were experimentally tested via enzyme assay and they showed cyclooxygenase-2 inhibition activity in the middle micro molar range (4b had a COX-1 IC50 of 26 μM and a COX-2 IC50 of 34 μM, 3b had a COX-1 IC50 of 19 μM and a COX-2 IC50 of 31 μM, 3a had a COX-2 IC50 of 42 μM). These compounds were analyzed via docking and were predicted to interact with some of the COX-2 key residues. Our best hit, 4d (COX-1 IC50 of 28 μM, COX-2 IC50 of 23 μM), appears to adopt similar binding modes to the standard COX-2 inhibitor, celecoxib, proposing room for possible selectivity. Additionally, the resultant novel compounds were tested in several in vivo assays. Four compounds 3a (COX-2 IC50 of 42 μM), 3d, 4d and 4f were notable for their anti-inflammatory activity that was comparable to that of the clinically available COX-2 inhibitor celecoxib. Interestingly, they showed greater potency than the famous non-steroidal anti-inflammatory drug, Diclofenac sodium. In summary, these novel pyrazolo[3,4-d]pyrimidine analogues showed interesting anti-inflammatory activity and could act as a starting point for future drugs.

ECTONUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE 1 (ENPP1) MODULATORS AND USES THEREOF

Provided herein are small molecule modulators of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

Synthesis of pyrazole-carboxamides and pyrazole-carboxylic acids derivatives: Simple methods to access powerful building blocks

Hybrid systems containing pyrazole moiety show a wide spectrum of biological activities. To access novel hybrids with pyrazole ring, in this work we synthesized twenty pyrazole-carboxylic acids and twenty pyrazole-carboxamides, using simple synthetic methods, to be used as building blocks in the development of new structures.

Identification of 1-phenyl-4-cyano-5-aminopyrazoles as novel ecdysone receptor ligands by virtual screening, structural optimization, and biological evaluations

Ecdysteroids initiate the molting process in insects by binding to the ecdysone receptor (EcR), which is a promising target for identifying insect growth regulators. This paper presents an in silico/in vitro screening procedure for identifying new EcR ligands. The three-step virtual screening procedure uses a three-dimensional pharmacophore model, docking and Molecular Mechanics/Poisson–Boltzmann Surface Area (MM/PBSA) rescoring routine. A novel hit (VS14) with good binding activity against Plutella xylostella EcR was identified from a library of over 200,000 chemicals. Subsequently, the 1-phenyl-4-cyano-5-aminopyrazole scaffold and twelve EcR ligands were synthesized. Their IC50 values against Plutella xylostella EcR ranged from 0.64 to 23.21?μm. Furthermore, a preliminary analysis of the structure–activity relationship for novel scaffolds provided a basis for designing new ligands with improved activity.

COMBINATION THERAPY FOR TREATING MPS1

The application is directed to compounds of formula (I) and their salts and solvates, wherein B, R1, R2, R3, R3', R4, R4', and R5 are as set forth in the specification, as well as to methods for their preparation, pharmaceutical compositions comprising the same, and use thereof for the treatment and/or prevention of, e.g., MPS1, optionally in combination with α-L-iduronidase or an analog or variant thereof, e.g., laronidase.

Pharmacophore-linked pyrazolo[3,4-d]pyrimidines as EGFR-TK inhibitors: Synthesis, anticancer evaluation, pharmacokinetics, and in silico mechanistic studies

Targeting the epidermal growth factor receptors (EGFRs) with small inhibitor molecules has been validated as a potential therapeutic strategy in cancer therapy. Pyrazolo[3,4-d]pyrimidine is a versatile scaffold that has been exploited for developing potential anticancer agents. On the basis of fragment-based drug discovery, considering the essential pharmacophoric features of potent EGFR tyrosine kinase (TK) inhibitors, herein, we report the design and synthesis of new hybrid molecules of the pyrazolo[3,4-d]pyrimidine scaffold linked with diverse pharmacophoric fragments with reported anticancer potential. These fragments include hydrazone, indoline-2-one, phthalimide, thiourea, oxadiazole, pyrazole, and dihydropyrazole. The synthesized molecules were evaluated for their anticancer activity against the human breast cancer cell line, MCF-7. The obtained results revealed comparable antitumor activity with that of the reference drugs doxorubicin and toceranib. Docking studies were performed along with EGFR-TK and ADMET profiling studies. The results of the docking studies showed the ability of the designed compounds to interact with key residues of the EGFR-TK through a number of covalent and noncovalent interactions. The obtained activity of compound 25 (IC50 = 2.89 μM) suggested that it may serve as a lead for further optimization and drug development.

Microwave-assisted efficient synthesis of pyrazole-fibrate derivatives as stimulators of glucose uptake in skeletal muscle cells

The design and synthesis of a series of pyrazolo[3,4-d]pyrimidinones containing fibrate side chains have been accomplished by utilizing the concept of molecular hybridization. All the synthesized compounds were evaluated for the glucose uptake stimulatory effect in L6 rat skeletal muscle cells. Four compounds (3f, 3g, 3j and 3q) were found to show significant stimulation of glucose uptake. Further these four compounds have been examined for their Glut4 translocation stimulatory effect in L6-Glut4myc myotubes. Compound 3q was found to exert maximum increase in GLUT4myc translocation.

Discovery of novel multi-substituted benzo-indole pyrazole schiff base derivatives with antibacterial activity targeting DNA gyrase

The design and synthesis of novel multi-substituted benzo-indole pyrazole Schiff base derivatives of potent DNA gyrase inhibitory activity were the main aims of this study. All the novel synthesized compounds were examined for their antibacterial activities against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli, and Salmonella. In addition, we selected 20 compounds for the in vitro antibacterial activities assay of 6 drug-resistant bacteria strains. The result revealed compound 8I-w exhibited excellent antibacterial activity against 4 drug-resistant E. coli bacteria strains with IC50 values of 7.0, 17.0, 13.5, and 1.0 μM, respectively. In vitro enzyme inhibitory assay showed that compound 8I-w displayed potent inhibition against DNA gyrase with IC50 values of 0.10 μM. The molecular docking model indicated that compounds 8I-w can bind well to the DNA gyrase by interacting with various amino acid residues. This study demonstrated that the compound 8I-w can act as the most potent DNA gyrase inhibitor in the reported series of compounds and provide valuable information for the commercial DNA gyrase inhibiting bactericides.

Ultrasonic-Assisted Synthesis of Pyrazolo[3,4-d]pyrimidin-4-ol Tethered with 1,2,3-Triazoles and Their Anticancer Activity

Abstract: In the presents work synthesis and characterization of new heterocyclic derivatives containing pyrazolo[3,4-d]pyrimidine linkage with 1,4-disubstituted-1,2,3-triazoles via methylene-oxy group. The selected synthesized compounds were tested for their in-vitro anticancer activity against various cancer cell lines. Synthesis of compounds was done under ultrasonic-assisted Huisgen 1,3-dipolar cycloaddition reaction with good yields. Some of the newly synthesized compounds demonstrated good to moderate anticancer activity, most of compounds shows activity against renal cancer cell lines.