103646-82-8

Basic information

• Product Name: 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBONITRILE
• Synonyms: BUTTPARK 51\09-61;5-AMINO-1-P-TOLYL-1H-PYRAZOLE-4-CARBONITRILE;5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBONITRILE;5-AMINO-4-CYANO-1-(4-METHYLPHENYL)PYRAZOLE;4-(5-Amino-4-cyano-1H-pyrazol-1-yl)toluene, 5-Amino-4-cyano-1-(4-methylphenyl)-1H-pyrazole
• CAS NO: 103646-82-8
• Molecular Formula: C₁₁H₁₀N₄
• Molecular Weight: 198.22
• Mol File: 103646-82-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 116-120
• Boiling Point: 405.6 °C at 760 mmHg
• Flash Point: 199.1 °C
• Appearance: /
• Density: 1.23 g/cm³
• Vapor Pressure: 8.67E-07mmHg at 25°C
• Refractive Index: 1.651
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -0.58±0.10(Predicted)
• CAS DataBase Reference: 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(103646-82-8)
• EPA Substance Registry System: 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(103646-82-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 103646-82-8(Hazardous Substances Data)

Usage

General Description

5-amino-1-(4-methylphenyl)-1H-pyrazole-4-carbonitrile is a chemical compound with the molecular formula C10H9N5. It is a pyrazole derivative containing an amino group, a methylphenyl group, and a carbonitrile group. 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBONITRILE has potential biological and pharmaceutical applications due to its structural features, which may make it suitable for use in drug development or as a research tool in biochemistry and pharmacology. It is important to handle and use this compound safely and in accordance with appropriate laboratory practices and regulations.

InChI:InChI=1/C11H10N4/c1-8-2-4-10(5-3-8)15-11(13)9(6-12)7-14-15/h2-5,7H,13H2,1H3

Upstream product

• 123-06-8 Ethoxymethylenemalononitrile 
• 539-44-6 N-4-methylphenylhydrazine 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 86240-43-9 (ethoxymethylene)malononitrile 

Downstream Products

• 1150312-12-1 6-(5-amino-1-p-tolyl-1H-pyrazol-4-yl)-1-p-tolyl-1H-pyrazolo[3,4-d]-pyrimidin-4-amine 

Relevant articles and documents

Synthesis and anti-Plasmodium falciparum evaluation of novel pyrazolopyrimidine derivatives

Nine 1-phenyl-1H-pyrazolo[3,4-d]pyrimidine derivatives with different substituents in the 4-position of the phenyl group and benzenesulfonamide moiety were synthesized and evaluated against Plasmodium falciparum. Six compounds exhibited activity in vitro against the chloroquine-resistant clone W2 with IC50 values ranging from 5.13 to 12.22 μM. The most active derivative with substituents R1 = F / R2 = CH3 exhibited an IC50 value of 5.13 μM and an IS value of 62.90, which was higher than that of the control drug sulfadoxine. For this reason, it is possible to conclude that the 1H-pyrazolo[3,4-d]pyrimidine system is promising as a prototype for further studies of antimalarial candidates.

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.

Design, synthesis and insecticidal activities of N-(4-cyano-1-phenyl-1H-pyrazol-5-yl)-1,3-diphenyl-1H-pyrazole-4-carboxamide derivatives

Insect ryanodine receptor is one of the promising targets for the development of novel insecticides. In order to search for potent insecticides targeting the ryanodine receptor (RyR), a series of novel diphenyl-1H-pyrazole derivatives with cyano substituent were designed and synthesized. Their insecticidal activities against diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to high activities at the four concentrations. Among these compounds, N-(4-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)-3-phenyl-1H-pyrazole-4-carboxamide (5g) showed 84% larvicidal activity against Plutella xylostella at the concentration of 0.1 mg L-1. Molecular docking showed the predicted binding mode between 5g and protein receptor, which could suggest that the title compounds were the possible activators of insect RyR.

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.

Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: Design, synthesis and antibacterial activity

The identification of novel Topoisomerase II (Topo II) inhibitors is one of the most attractive directions in the field of bactericide research and development. In our ongoing efforts to pursue the class of inhibitors, six series of 70 novel coumarin-pyrazole carboxamide derivatives were designed and synthesized. As a result of the evaluation against four destructive bacteria, including Staphylococcus aureus, Listeria monocytogenes, Escherichia coli and Salmonella. Compound 8III-k (MIC = 0.25 mg/L) showed considerable inhibitory activity than ciprofloxacin (MIC = 0.5 mg/L) against Escherichia coli and 8V-c (MIC = 0.05 mg/L) exhibited excellent antibacterial activity than ciprofloxacin (MIC = 0.25 mg/L) against Salmonella. The selected compounds (8III-k, 8V-c and 8V-k) exhibit potent inhibition against Topo II and Topo IV with IC50 values (9.4–25 mg/L). Molecular docking model showed that the compounds 8V-c and 8V-k can bind well to the target by interacting with amino acid residues. It will provide some valuable information for the commercial Topo II inhibiting bactericides.