14678-90-1

Basic information

• Product Name: 5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID
• Synonyms: BUTTPARK 19\09-72;5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID;RARECHEM AL BO 1543
• CAS NO: 14678-90-1
• Molecular Formula: C₁₀H₈ClN₃O₂
• Molecular Weight: 237.64
• Mol File: 14678-90-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 454.7°Cat760mmHg
• Flash Point: 228.8°C
• Appearance: /
• Density: 1.55g/cm³
• Vapor Pressure: 4.66E-09mmHg at 25°C
• Refractive Index: 1.695
• CAS DataBase Reference: 5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID(14678-90-1)
• EPA Substance Registry System: 5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID(14678-90-1)

Safety Data

• Hazardous Substances Data: 14678-90-1(Hazardous Substances Data)

Usage

General Description

5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID is a chemical compound with the molecular formula C10H8ClN3O2. It is a derivative of pyrazole and contains an aminopyrazole group and a carboxylic acid group. 5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID is often used as a building block in the synthesis of pharmaceuticals and agrochemicals. It has been studied for its potential biological activities, including its use as an anti-inflammatory and analgesic agent. Additionally, it has shown potential as an inhibitor of certain enzymes and receptors in the human body. This chemical may have important applications in the development of new drugs and treatments for various diseases.

InChI:InChI=1/C10H8ClN3O2/c11-6-1-3-7(4-2-6)14-9(12)8(5-13-14)10(15)16/h1-5H,12H2,(H,15,16)

Upstream product

• 1073-69-4 N-4-chlorophenylhydrazine 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 14678-87-6 ethyl 5-amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate 

Downstream Products

• 1349199-09-2 (E)-5-(benzylideneamino)-1-(4-chlorophenyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 
• 1349199-10-5 (E)-1-(4-chlorophenyl)-5-(4-methoxybenzylideneamino)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 
• 1349199-11-6 (E)-1-(4-chlorophenyl)-5-(4-hydroxy-3-methoxybenzylideneamino)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 
• 1349199-12-7 (E)-1-(4-chlorophenyl)-5-(3,4-dimethoxybenzylideneamino)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 
• 1349199-13-8 (E)-1-(4-chlorophenyl)-6-methyl-5-(3,4,5-trimethoxybenzylideneamino)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 
• 1349199-08-1 5-amino-1-(4-chlorophenyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 

Relevant articles and documents

Novel Pyrazolo[3,4- d]pyrimidin-4-one Derivatives as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation

Plant pathogenic fungi seriously threaten agricultural production. There is an urgent need to develop novel fungicides with low toxicity and high efficiency. In this study, we designed and synthesized 44 pyrazolo[3,4-d]pyrimidin-4-one derivatives and evaluated them for their fungicidal activities. The bioassay data revealed that most of the target compounds possessed moderate to high in vitro antifungal activities. Especially compound g22 exhibited remarkable antifungal activity against Sclerotinia sclerotiorum with an EC50 value of 1.25 mg/L, close to that of commercial fungicide boscalid (EC50 = 0.96 mg/L) and fluopyram (EC50 = 1.91 mg/L). Moreover, compound g22 possessed prominent protective activity against S. sclerotiorum in vivo for 24 h (95.23%) and 48 h (93.78%), comparable to positive control boscalid (24 h (96.63%); 48 h (93.23%)). Subsequent studies indicated that compound g22 may impede the growth and reproduction of S. sclerotiorum by affecting the morphology of mycelium, destroying cell membrane integrity, and increasing cell membrane permeability. In addition, the application of compound g22 did not injure the growth or reproduction of Italian bees. This study revealed that compound g22 is expected to be developed for efficient and safe agricultural fungicides.

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.

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.