132603-45-3

Basic information

• Product Name: 4-(1H-indol-3-ylmethylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
• Synonyms: 3H-Pyrazol-3-one, 2,4-dihydro-4-(1H-indol-3-ylmethylene)-5-methyl-2-phenyl-, (Z)- (9CI)
• CAS NO: 132603-45-3
• Molecular Formula: C₁₉H₁₅N₃O
• Molecular Weight: 301.3419
• Mol File: 132603-45-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(1H-indol-3-ylmethylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1H-indol-3-ylmethylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one(132603-45-3)
• EPA Substance Registry System: 4-(1H-indol-3-ylmethylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one(132603-45-3)

Safety Data

• Hazardous Substances Data: 132603-45-3(Hazardous Substances Data)

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 89-25-8 edaravone 
• 86-92-0 3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one 
• 539-44-6 N-4-methylphenylhydrazine 
• 141-97-9 ethyl acetoacetate 
• 100-63-0 phenylhydrazine 

Downstream Products

• 61466-03-3 5-methyl-4-[(5-methyl-3-oxo-2-phenyl-2,4-dihydro-3H-pyrazol-4-yl)methylene]-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 

Relevant articles and documents

Azines and their acyclic derivatives as transferers of one-carbon fragment in reactions with pyrazolones

Enehydrazine derivatives have been obtained by the reaction of 6-phenyl-1,2,4-triazine 4-oxide with pyrazolones 2, which on further heating with pyrazolones 2 are converted into the corresponding symmetrical or unsymmetrical derivatives of dipyrazolylmethane. Enehydrazine derivatives of 1,3-dimethyl-5-nitrosouracil and 1,3-dimethylimidazolidine interact with 3-methyl-1-phenyl-5-pyrazolone (2a) with the formation of dipyrazolylmethane derivative. On interacting compound 2a or 3-methyl-1-(p-nitrophenyl)-5-pyrazolone with 3,6-diphenyl-1,2,4-triazine 4-oxide 12 the corresponding 4,4′-bispyrazolones are formed, but the interaction of compound 12 with 3-(p-nitrophenyl)-1-phenyl-5-pyrazolone leads to dipyrazolylmethane derivative. Dipyrazolylmethane derivative is obtained on heating of fervenulin 4-oxide, 2,4-dihydroxy-5-nitropyrimidine, and 1,3,5-triazines: 6-azauracil, 5-azauracil, azacytosine, and 2,4-diamino-s-triazine with pyrazolone 2a.

An SiO2/ZnBr2 mediated expeditious approach to 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one derivatives in water under microwave irradiation

A new one-pot three-component green approach has been developed for the synthesis of a series of pyrazolone derivatives 2(a-s) from differently substituted aromatic aldehydes, ethylacetoacetate and phenylhydrazine/2,4-dinitrophenylhydrazine in excellent y

Synthesis, crystal structure and evaluation of cancer inhibitory activity of 4-[indol-3-yl-methylene]-1H-pyrazol-5(4H)-one derivatives

A series of 4-(1H-indol-3-yl-methylene)-1H-pyrazol-5(4H)-one derivatives have been synthesised. The Z structure of 4-[(1-methyl-1H-indol-3-yl)methylene]- 3-phenyl-1-p-tolyl-1H-pyrazol-5-one was determined by X-ray crystallography. The antitumour activity was evaluated against five cancer cells by MTT assay. [(1H-Indol-3-yl)methylene]-1-(2,4-dinitrophenyl)- 3-methyl-1H-pyrazole-5-one and 4-{4-[(1-benzyl-1H-indol-3-yl)methylene]-3-methyl-5-oxo-4,5-dihydro-1Hpyrazol- 1-yl}-benzoic acid have similar anticancer activity with 5-UF on the test cancer cells (exception of A375). Almost all the target compounds displayed antitumour activity against A549 and PC-9, and those with benzyl at 1- position of indole had higher activity against PC-9 (IC50 value lower than 30 μM). Those with benzyl at the indole and carboxyl at the phenyl part of of pyrazole were more active against PC-9 and A549 cells, providing a good indication for subsequent optimisation as lung cancer inhibitory agents.

Clay Catalysis: Dry Condensation of 3-Methyl-1-phenyl-5-pyrazolone with Aldehydes under Microwave Irradiation

3-Methyl-1-phenyl-5-pyrazolone (1) and arylcarboxyaldehydes (2) were condensated to 1-phenyl-3-methyl-4-(arylmethylene)-5-pyrazolone (3) in presence of acidic clay KSF without solvent under microwave irradiation.