51516-68-8

Basic information

• Product Name: 5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE-&
• Synonyms: 5-aMino-1-(3-chlorophenyl)-1H-pyrazple-4-carbonitrile;5-Amino-1-(3-chlorophenyl);5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE-&;5-Amino-1-(3-chlorophenyl)pyrazole-4-carbonitrile
• CAS NO: 51516-68-8
• Molecular Formula: C₁₀H₇ClN₄
• Molecular Weight: 218.64238
• Product Categories: Pyrazoles;PyrazolesHeterocyclic Building Blocks;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 51516-68-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 183-187 °C
• Boiling Point: 438.5 °C at 760 mmHg
• Flash Point: 219 °C
• Appearance: /
• Density: 1.41 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.686
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -1.09±0.10(Predicted)
• CAS DataBase Reference: 5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE-&(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE-&(51516-68-8)
• EPA Substance Registry System: 5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE-&(51516-68-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36/39
• WGK Germany: 3
• PackingGroup: III
• Hazardous Substances Data: 51516-68-8(Hazardous Substances Data)

Usage

General Description

5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE is a chemical compound with the molecular formula C9H8ClN3. It is a pyrazole derivative, which is a class of organic compounds that contain a five-membered ring with three carbon atoms and two nitrogen atoms. 5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE-& is a pale yellow solid with a molecular weight of 187.63 g/mol. It is commonly used in organic synthesis, medicinal chemistry, and as a building block in the production of pharmaceuticals. Specifically, it has been studied for its potential antitumor and anticancer properties, making it of interest for further research and development in the pharmaceutical industry.

InChI:InChI=1/C10H7ClN4/c11-8-3-1-2-4-9(8)15-10(13)7(5-12)6-14-15/h1-4,6H,13H2

Upstream product

• 2312-23-4 m-chlorophenylhydrazine hydrochloride 
• 123-06-8 Ethoxymethylenemalononitrile 
• 108-42-9 3-chloro-aniline 
• 14763-20-3 3-chlorophenyl hydrazine 
• 122-51-0 orthoformic acid triethyl ester 
• 109-77-3 malononitrile 

Downstream Products

• 135108-74-6 4-Amino-5-butyl-1-(3-chloro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 1094618-86-6 1-(3-chlorophenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[3,4-b]quinolin-4-amine 
• 1094618-90-2 1-(3-chlorophenyl)-1,5,6,7-tetrahydrocyclopenta[e]pyrazolo[3,4-b]pyridin-4-amine 
• 1269662-45-4 ethyl 4-amino-1-(3-chlorophenyl)-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 1269662-38-5 methyl 4-amino-1-(3-chlorophenyl)-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 50427-78-6 5-amino-1-(3-chlorophenyl)-1H-pyrazole-4-carboxamide 
• 1613037-28-7 5-[5-amino-1-(3′-chlorophenyl)-1H-pyrazole-4-yl]-1H-tetrazole 
• 1452871-37-2 C₁₄H₁₂ClN₅O 
• 1452871-34-9 C₁₃H₁₀ClN₅O 
• 1431459-14-1 5-[1-(3-chlorophenyl)-1H-pyrazole-4-yl]-1H-tetrazole 
• 1350554-91-4 1-(3-chlorophenyl)-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazole 
• 1174310-23-6 5-amino-1-(3-chlorophenyl)-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazole 
• 58791-87-0 1-(3-chloro-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine 
• 138548-44-4 4-amino-1-(3-chlorophenyl)-5H-pyrazolo<3,4-d>pyrimidin-6-one 

Relevant articles and documents

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.

Synthesis, structure-activity relationship and trypanocidal activity of pyrazole-imidazoline and new pyrazole-tetrahydropyrimidine hybrids as promising chemotherapeutic agents for Chagas disease

Drug therapy for Chagas disease remains a major challenge as potential candidate drugs have failed clinical trials. Currently available drugs have limited efficacy and induce serious side effects. Thus, the discovery of new drugs is urgently needed in the fight against Chagas' disease. Here, we synthesized and evaluated the biological effect of pyrazole-imidazoline (1a-i) and pyrazole-tetrahydropyrimidine (2a-i) derivatives against relevant clinical forms of Trypanosoma cruzi. The structure-activity relationship (SAR), drug-target search, physicochemical and ADMET properties of the major active compounds in vitro were also assessed in silico. Pyrazole derivatives showed no toxicity in Vero cells and also no cardiotoxicity. Phenotypic screening revealed two dichlorinated pyrazole-imidazoline derivatives (1c and 1d) with trypanocidal activity higher than that of benznidazole (Bz) against trypomastigotes; these were also the most potent compounds against intracellular amastigotes. Replacement of imidazoline with tetrahydropyrimidine in the pyrazole compounds completely abolished the trypanocidal activity of series 2(a-i) derivatives. The physicochemical and ADMET properties of the compounds predicted good permeability, good oral bioavailability, no toxicity and mutagenicity of 1c and 1d. Pyrazole nucleus had high frequency hits for cruzipain in drug-target search and structure activity relationship (SAR) analysis of pyrazole-imidazoline derivatives revealed enhanced activity when chlorine atom was inserted in meta-positions of the benzene ring. Additionally, we found evidence that both compounds (1c and 1d) have the potential to interact non-covalently with the active site of cruzipain and also inhibit the cysteine proteinase activity of T. cruzi. Collectively, the data presented here reveal pyrazole derivatives with promise for further optimization in the therapy of Chagas disease.

Effectiveness of novel 5-(5-amino-1-aryl-1H-pyrazol-4-yl)-1H-tetrazole derivatives against promastigotes and amastigotes of leishmania amazonensis

In this research, a series of substituted 5-(5-amino-1-aryl-1H-pyrazol-4- yl)-1H-tetrazoles were synthesized and evaluated for in vitro antileishmanial activity. Among the derivatives, examined compounds 3b and 3l exhibited promising activity against promastigotes and amastigotes forms of Leishmania amazonensis. The cytotoxicity of these compounds was evaluated on murine cells, giving access to the corresponding selectivity index (SI).