53316-56-6

Basic information

• Product Name: 3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-4-[(4-methylphenyl)methylene]-2-phenyl-
• CAS NO: 53316-56-6
• Molecular Formula: C18H16N2O
• Molecular Weight: 276.338
• Mol File: 53316-56-6.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-4-[(4-methylphenyl)methylene]-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-4-[(4-methylphenyl)methylene]-2-phenyl-(53316-56-6)
• EPA Substance Registry System: 3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-4-[(4-methylphenyl)methylene]-2-phenyl-(53316-56-6)

Safety Data

• Hazardous Substances Data: 53316-56-6(Hazardous Substances Data)

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 89-25-8 edaravone 
• 62-53-3 aniline 
• 589-18-4 4-Methylbenzyl alcohol 
• 100-63-0 phenylhydrazine 

Downstream Products

• 143699-05-2 4,4'-((4-methylphenyl)methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) 
• 1422554-91-3 C₂₈H₂₄N₄O₂S 
• 1429035-04-0 4-benzyl-4-((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(p-tolyl)methyl)-2-phenyloxazol-5(4H)-one 
• 1453187-41-1 (4S,5S)-5-benzyl-3-methyl-1-phenyl-4-p-tolyl-4,5-dihydropyrano[2,3-c]pyrazol-6(1H)-one 
• 1453187-54-6 (4S,5S)-5-decyl-3-methyl-1-phenyl-4-p-tolyl-4,5-dihydropyrano[2,3-c]pyrazol-6(1H)-one 
• 1569091-36-6 C₃₄H₂₈N₄O₂S 

Relevant articles and documents

Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy

Serine, the source of the one-carbon units essential for de novo purine and deoxythymidine synthesis plays a crucial role in the growth of cancer cells. Phosphoglycerate dehydrogenase (PHGDH) which catalyzes the first, rate-limiting step in de novo serine biosynthesis has become a promising target for the cancer treatment. Here we identified H-G6 as a potential PHGDH inhibitor from the screening of an in-house small molecule library based on the enzymatic assay. We adopted activity-directed combinatorial chemical synthesis strategy to optimize this hit compound. Compound b36 was found to be the noncompetitive and the most promising one with IC50 values of 5.96 ± 0.61 μM against PHGDH. Compound b36 inhibited the proliferation of human breast cancer and ovarian cancer cells, reduced intracellular serine synthesis, damaged DNA synthesis, and induced cell cycle arrest. Collectively, our results suggest that b36 is a novel PHGDH inhibitor, which could be a promising modulator to reprogram the serine synthesis pathway and might be a potential anticancer lead worth further exploration.

Enantio- And diastereoselective synthesis of b-Aryl-b-pyrazolyl a-amino acid esters via copper-catalyzed reaction of azomethine ylides with benzylidenepyrazolones

A fully stereoselective synthesis of unnatural chiral b-aryl-b-pyrazolyl a-amino acid esters via copper-catalyzed addition reactions of azomethine ylides with benzylidenepyrazolones bearing two contiguous stereogenic centers was developed. A 1H-pyrazol-5-ol was introduced by the aromatization of 3H-pyrazol-3-one in the reaction. The transformation operated at room temperature and afforded b-1H-pyrazol-5-ol-a-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.

Organocatalytic Asymmetric Michael/Hemiketalization/Retro-aldol Reaction of α-Nitroketones with Unsaturated Pyrazolones: Synthesis of 3-Acyloxy Pyrazoles

An organocatalytic asymmetric cascade Michael/hemiketalization/retro-aldol reaction between unsaturated pyrazolones and α-nitroketones is described. A bifunctional thiourea catalyst was found to be efficient for this reaction. With 10 mol % of catalyst, high yields as well as excellent enantioselectivities are attained for a variety of 3-acyloxy pyrazoles under mild reaction conditions.