58791-78-9

Basic information

• Product Name: 5-AMINO-1-(3,4-DICHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE
• Synonyms: AKOS BBS-00002123;5-AMINO-1-(3,4-DICHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE;5-Amino-4-cyano-1-(3,4-dichlorophenyl)-1H-pyrazole
• CAS NO: 58791-78-9
• Molecular Formula: C₁₀H₆Cl₂N₄
• Molecular Weight: 253.09
• Mol File: 58791-78-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 170
• Boiling Point: 460.9 °C at 760 mmHg
• Flash Point: 232.5 °C
• Appearance: /
• Density: 1.54 g/cm³
• Vapor Pressure: 1.12E-08mmHg at 25°C
• Refractive Index: 1.701
• CAS DataBase Reference: 5-AMINO-1-(3,4-DICHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1-(3,4-DICHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(58791-78-9)
• EPA Substance Registry System: 5-AMINO-1-(3,4-DICHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(58791-78-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 58791-78-9(Hazardous Substances Data)

Usage

General Description

5-AMINO-1-(3,4-DICHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE is a chemical compound with the molecular formula C9H5Cl2N5. It is a pyrazole derivative with a carbonitrile functional group, and it contains a 3,4-dichlorophenyl substitution. 5-AMINO-1-(3,4-DICHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE has potential applications in the field of medicinal chemistry, particularly in the development of pharmaceutical drugs. Its unique structure and properties make it a valuable tool for researchers and scientists working on drug discovery and development. Additionally, it may have potential uses in other industries, such as agriculture or materials science, due to its diverse chemical properties. Understanding the behavior and potential applications of 5-AMINO-1-(3,4-DICHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE is important for advancing scientific knowledge and potentially unlocking new solutions to real-world problems.

InChI:InChI=1/C10H6Cl2N4/c11-8-2-1-7(3-9(8)12)16-10(14)6(4-13)5-15-16/h1-3,5H,14H2

Upstream product

• 123-06-8 Ethoxymethylenemalononitrile 
• 13124-18-0 3,4-dichlorophenylhydrazine 
• 19763-90-7 3,4-dichlorophenylhydrazine hydrochloride 

Downstream Products

• 1350554-97-0 5-amino-1-(3,4-dichlorophenyl)-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazole 
• 1350554-92-5 1-(3,4-dichlorophenyl)-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazole 
• 1613037-30-1 5-[5-amino-1-(3′,4′-dichlorophenyl)-1H-pyrazole-4-yl]-1H-tetrazole 
• 1431459-25-4 5-[1-(3,4-dichlorophenyl)-1H-pyrazole-4-yl]-1H-tetrazole 

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.

An efficient synthesis of new 5-(1-Aryl-1H-pyrazole-4-yl)-1H-tetrazoles from 1-Aryl-1H-pyrazole-4-carbonitriles via [3 + 2] cycloaddition reaction

A series of new 5-(1-aryl-1H-pyrazole-4-yl)-1H-tetrazoles 4a-l were synthesized via [3 + 2] cycloaddition reaction from 1-aryl-1H-pyrazole-4- carbonitriles 3a-l, sodium azide and ammonium chloride, using dimethylformamide (DMF) as solvent, in good yields: 64-85%. The structures of these newly synthesized compounds were determined from the IR, 1H- and 13C-NMR spectroscopic data and elemental analyses.