109466-44-6

Basic information

• Product Name: 5-methyl-N,1-diphenyl-1H-pyrazole-4-carboxamide
• Synonyms: 5-methyl-N,1-diphenyl-1H-pyrazole-4-carboxamide
• CAS NO: 109466-44-6
• Molecular Formula: C₁₇H₁₅N₃O
• Molecular Weight: 277.3205
• Mol File: 109466-44-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-methyl-N,1-diphenyl-1H-pyrazole-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-N,1-diphenyl-1H-pyrazole-4-carboxamide(109466-44-6)
• EPA Substance Registry System: 5-methyl-N,1-diphenyl-1H-pyrazole-4-carboxamide(109466-44-6)

Safety Data

• Hazardous Substances Data: 109466-44-6(Hazardous Substances Data)

Upstream product

• 80421-00-7 2-(Anilinomethylen)-3-oxo-N-phenyl-butanamid 
• 100-63-0 phenylhydrazine 
• 133620-27-6 2-acetyl-3-p-toluidino-acrylic acid anilide 
• 62-53-3 aniline 
• 1831-98-7 2-(ethoxymethylene)-3-oxo-N-phenylbutanamide 
• 102-01-2 N-phenylacetoacetamide 

Relevant articles and documents

Synthesis and biofilm formation reduction of pyrazole-4-carboxamide derivatives in some Staphylococcus aureus strains

The ability of several N-phenyl-1H-pyrazole-4-carboxamide derivatives and other pyrazoles opportunely modified at the positions 3, 4 and 5, to reduce the formation of the biofilm in some Staphylococcus aureus strains (ATCC 29213, ATCC 25923 and ATCC 6538) were investigated. All the tested compounds were able, although to a different extent, to reduce the biofilm formation of the three bacterial strains considered. Among these, the 1-(2,5-dichlorophenyl)-5-methyl-N-phenyl-1H-pyrazole-4-carboxamide 14 resulted as the best inhibitor of biofilm formation showing an IC50ranging from 2.3 to 32 μM, against all the three strains of S. aureus. Compound 14 also shows a good protective effect in vivo by improving the survival of wax moth larva (Galleria mellonella) infected with S. aureus ATCC 29213. These findings indicate that 14d is a potential lead compound for the development of new anti-virulence agents against S. aureus infections.

1-(N,N-dimethylamino)-2-(N-phenylcarbamoyl)-1-buten-3-one as a building block for the synthesis of heterocyclic compounds

Acetoacetanilide 1 reacted with DMF-DMA to give the enaminone 2. Compound 2, when treated with hydrazines gives the pyrazoles 4a and 4b respectively, and with pyrazole derivatives 5a and 5b the pyrazolopyrimidines 7. On the other hand, in reaction of 2 with benzimidazole and benzimidazole-2-acetonitrile, the pyrimidobenzimidazole 14 and the pyridobenzimidazole 17 were formed. 2 reacts with hippuric acid in boiling acetic anhydride to afford the pyridine 20. In the reaction of 2 with malononitrile, cyanoacetamide or malononitrile dimer compounds 21, 22 and 24 were formed. Compound 22 was further reacted with arylidenemalononitriles to give the benzopyridine derivatives 28. Pyridone 22 treated with S-DMF mixture gives thienopyridine 29, while refluxed with DMFDMA yielded the pyridopyridine 30.