957298-57-6

Basic information

• Product Name: 5-amino-3-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole-4-carbonitrile
• Synonyms: 5-amino-3-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole-4-carbonitrile
• CAS NO: 957298-57-6
• Molecular Formula: C₁₂H₁₂N₄O₂S
• Molecular Weight: 276.31428
• Mol File: 957298-57-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-amino-3-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole-4-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-3-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole-4-carbonitrile(957298-57-6)
• EPA Substance Registry System: 5-amino-3-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole-4-carbonitrile(957298-57-6)

Safety Data

• Hazardous Substances Data: 957298-57-6(Hazardous Substances Data)

Upstream product

• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 5417-82-3 (1-ethoxyethylidene)malononitrile 
• 78-39-7 Triethyl orthoacetate 
• 109-77-3 malononitrile 

Downstream Products

• 1298095-82-5 3-methyl-1-tosyl-1,7-dihydro-pyrazolo[3,4-d]pyrimidine-4,6-dithione 
• 1298095-88-1 5-methyl-2-(4-methoxyphenyl)-7-tosyl-2-thioxo-1,2,3,7-tetrahydropyrazolo[3,4-d]-[1,3,2]diazaphosphinine-4-thione 

Relevant articles and documents

Synthesis of aminocyanopyrazoles via a multi-component reaction and anti-carbonic anhydrase inhibitory activity of their sulfamide derivatives against cytosolic and transmembrane isoforms

A convenient protocol for the multicomponent reaction (MCRs) between malononitrile with an orthoester and hydrazine derivatives, under acid catalyst is described. A series of aminocyanopyrazoles 4 was prepared, isolated and characterized. These pyrazoles reacted with sodium nitrite followed by secondary amine reagent and with formic acid to lead pyrazolotriazines 6 and pyrazolopyrimidinones 7. Some of the aminopyrazoles were converted to the corresponding sulfamides by reaction with sulfamoyl chloride. The aminopyrazoles incorporating phenyl and tosyl moieties were tested as inhibitors of four carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the human (h) hCA I, II, IX and XII. Many of them showed low micromolar or submicromolar inhibition of these enzymes. The corresponding sulfamides were low nanomolar CA inhibitors.

Synthesis of new pyrazolopyrimidinedithiones and pyrazolopyrimidinephosphines from aminocyanopyrazoles

A general, high-yielding synthetic protocol for the expedited synthesis of functionalized pyrazolopyrimidine dithione 2 and pyrazolodiazaphosphininethione 3 from amino-cyano pyrazole 1 precursors is presented.