68901-70-2

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 89-25-8 edaravone 
• 942-32-5 5-methyl-2-phenyl-2H-pyrazol-3-ol 
• 785-80-8 p-nitrobenzylideneaniline 
• 96068-42-7 4,4'-[(4-nitrophenyl)methylene]bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) 
• 57-13-6 urea 
• 619-73-8 4-nitrobenzyl chloride 
• 62-53-3 aniline 
• 100-63-0 phenylhydrazine 

Downstream Products

• 96128-62-0 5-Methyl-4-[(3-methyl-1-phenyl-5-thioxo-4,5-dihydro-1H-pyrazol-4-yl)-(4-nitro-phenyl)-methyl]-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 68615-46-3 5-methyl-4-(4-nitro-benzylidene)-2-phenyl-2,4-dihydro-pyrazole-3-thione 
• 96068-42-7 4,4'-[(4-nitrophenyl)methylene]bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) 

Relevant academic research and scientific papers

A three-component, general and practical route for diastereoselective synthesis of aza-spirocyclic pyrazolonesviaa decarboxylative annulation process

An efficient, general, and practical route for highly diastereoselective synthesis of aza-spirocyclic pyrazolones from easily available α-amino acids, aldehydes, and alkylidene pyrazolones by means of a decarboxylative annulation process is reported. This

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 β-Aryl-β-pyrazolyl α-Amino Acid Esters via Copper-Catalyzed Reaction of Azomethine Ylides with Benzylidenepyrazolones

A fully stereoselective synthesis of unnatural chiral β-aryl-β-pyrazolyl α-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 β-1H-pyrazol-5-ol-α-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.

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.

Palladium N-heterocyclic carbene catalyzed expected and unexpected C-C and C-N functionalization reactions of 1-aryl-3-methyl-1: H -pyrazol-5(4 H)-ones

A palladium N-heterocyclic carbene [Pd(NHC)Cl2] complex of vitamin B1 developed earlier in our laboratory was successfully employed as an efficient catalyst for the regioselective C-C and C-N functionalization reactions of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones 1a-b. The catalyst was attempted for the C-H arylation, acylation and alkoxylation of 1a-b using the respective coupling substrates such as aryl iodides 2a-c, benzylic alcohols 3a-d and methanol/ethanol 4. It was surprisingly noted that the acylation and alkoxylation reactions underwent a diverse pathway to yield some unexpected products rather than the targeted ones. In the case of the arylation reactions only the targeted products have been observed. This has made the protocol very interesting compared to the conventional coupling reactions.

Study on one-pot biginelli-like synthesis of pyrazolo[3,4-d]pyrimidines in bronsted acidic ionic liquid under sonication and its mechanism

Pyrazolo[3,4-d]pyrimidine derivatives were synthesized using ionic liquid, 1-butylimidazolium tetrafluoroborate, under ultrasound irradiation at ambient condition without any added catalyst. Mechanistic pathway based on the catalytic role of ionic liquid has been proposed. This method offers the advantages of simple procedure, milder reaction condition, easier workup and improved yield over the conventional method. The ionic liquid could be recycled at least three times with marked retention in its activity.

KF-Al2O3 catalyzed the condensations of 2-methylbenzoxazole and pyrazol-5-one with aromatic aldehydes

In the presence of KF-Al2O3 as a solid base, 2-methylbenzoxazole 1 in DMF and 1-phenyl-3-methylpyrazol-5-one 2 in methanol, respectively, reacted with aromatic aldehydes to give 2-styrylbenzoxazoles 4a-f in high yields and 1-phenyl-3

The Solid-State Michael Addition of 3-Methyl-1-phenyl-5-pyrazolone

A novel solid-state Michael addition between pyrazolone 1 and 4-arylidenepyrazolones 2 at ambient temperature produced Michael adducts, 4,4′-arylidenebis(3-methyl-1-phenyl-5-pyrazolones) 3. Pyrazolones 3 formed salts 4 with Cu2+ in solution, indicating the enolic structure of the pyrazolone rings. The reactivity of 2 with 1 is discussed in terms of the electronic and steric effects of the substituent on the arylidene group of compounds 2. Pyrazolone 1 also underwent the solid state Michael addition reaction with maleimide at 100° to give the adducts 7, 8 and 9.

New Aspects in the Reaction of Azomethines with Cyclic CH-Acidic Compounds

Treatment of substituted benzylidene anilines 1a - f with cyclic CH-acidic compounds 2a - m in ethanol at room temperature yields in addition/elimination reactions the corresponding arylidene derivatives 4 and the 2:1 adducts 5.The addition products 3, which are formed as intermediates, could not be isolated in any case.The donor/acceptor effect of the substituents on the benzylidene moiety influences to a significant extent the reactivity towards the azomethine carbon. Keywords.Azomethine; CH-Acidic compound; Addition/elimination reaction.