13024-90-3

Usage

Chemical Properties

light yellow crystals

Upstream product

• 108161-18-8 5-Methyl-4-(1-methylethylidene)-2-(4'-chlorophenyl)-2,4-dihydro-3H-pyrazol-3-one 
• 29425-96-5 2-(4-chlorophenyl)-5-methylpyrazolidin-3-one 
• 674-82-8 4-methyleneoxetan-2-one 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 106-47-8 4-chloro-aniline 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 4426-72-6 hydrazine carboxamide 

Downstream Products

• 70733-38-9 2-(4-chloro-phenyl)-5-methyl-4-thiophen-2-ylmethylene-2,4-dihydro-pyrazol-3-one 
• 70733-69-6 2-(4-chloro-phenyl)-5-methyl-4-(1-thiophen-2-yl-ethylidene)-2,4-dihydro-pyrazol-3-one 
• 67365-79-1 2-(4-chloro-phenyl)-5-methyl-4-(5-nitro-furan-2-ylmethylene)-2,4-dihydro-pyrazol-3-one 
• 74169-54-3 1-(4-chlorophenyl)-3,4-dimethylpyrano<2,3-c>pyrazole-6(1H)-one 
• 96138-42-0 3-[1-(4-Chloro-phenyl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-(4Z)-ylidene]-butyric acid ethyl ester 
• 108161-22-4 5-Methyl-4-(1'-methyl-4'-oxopenta-2'-yl)-2-(4''-chlorophenyl)-2,4-dihydro-3H-pyrazol-3-one 
• 108161-18-8 5-Methyl-4-(1-methylethylidene)-2-(4'-chlorophenyl)-2,4-dihydro-3H-pyrazol-3-one 
• 108221-71-2 C₂₅H₂₂Cl₂N₄O₂ 
• 111751-08-7 2-(4-Chloro-phenyl)-4-isopropyl-5-methyl-1,2-dihydro-pyrazol-3-one 
• 1186372-63-3 1-(4'-chlorophenyl)-4-formyl-5-hydroxy-3-methylpyrazole 
• 118030-33-4 1-(4-chlorophenyl)-4-((dimethylamino)methylene)-3-methyl-1H-pyrazol-5(4H)-one 
• 75897-87-9 (2-chlorophenyl)[1-(4-chlorophenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl]methanone 
• 31829-19-3 C₁₆H₁₂ClN₅O₃ 
• 1400890-58-5 C₁₆H₁₁ClN₆O₅ 

Relevant academic research and scientific papers

Hydroxyl radical scavenging by edaravone derivatives: Efficient scavenging by 3-methyl-1-(pyridin-2-yl)-5-pyrazolone with an intramolecular base

We synthesized various 3-methyl-1-phenyl-5-pyrazolone (edaravone) derivatives and evaluated their oxidation potential and hydroxyl radical scavenging activity. It was found 3-methyl-1-(pyridin-2-yl)-5-pyrazolone had a much higher ability to scavenge the radical than did edaravone itself. Its efficient radical scavenging activity was assumed to be due to the increase of its anion form, an active form, by a hydrogen-bonded intramolecular base.

Tungstophosphoric acid-catalyzed synthesis of pyrazolones in water

A convenient and efficient method for the synthesis of pyrazolones via condensation of hydrazine derivatives with β-keto esters in water catalyzed by tungstophosphoric acid is described. It eliminates the need to dry solvents and substrates before use and the products are easily isolated with high yields.

DABCO-catalyzed silver-promoted direct thiolation of pyrazolones with diaryl disulfides

A highly efficient protocol for a direct thiolation of N-substituted pyrazolones with diaryl disulfides is described. Using a combination of DABCO and silver(i) acetate, the C-S bond formation proceeds smoothly at room temperature under mild and easy to handle conditions. This synthetic strategy offers a convenient and direct modification of antipyrine and other pyrazolone substrates, giving a series of aryl sulfide-substituted pyrazolone products in moderate to excellent yields.

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.

Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones

The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.

Catalytic System-Controlled Divergent Reaction Strategies for the Construction of Diversified Spiropyrazolone Skeletons from Pyrazolidinones and Diazopyrazolones

A catalytic system-controlled divergent reaction strategy was here reported to construct four types of intriguing spiroheterocyclic skeletons from simple and readily available starting materials via a precise chemical bond activation/[n+1] annulation cascade. The tetraazaspiroheterocyclic and trizazspiroheterocyclic scaffolds could be independently constructed by a selective N?N bond activation/[n+1] annulation cascade, a C(sp2)-H activation/[4+1] annulation and a novel tandem C(sp2)-H/C(sp3)?H bond activation/[4+1] annulation strategy, along with a broad scope of substrates, moderate to excellent yields and valuable transformations. More importantly, in these transformations, we are the first time to capture a N?N bond activation and a C(sp3)?H bond activation of pyrazolidinones under different catalytic system.

Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions

An electrochemical oxidative cross-coupling reaction between 2.5-substituted-pyrazolin-5-ones and ammonium thiocyanate has been developed, which resulted in a series of unprecedented cross-coupling products under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions. It is worth noting that since the resulting cross-coupling products are nearly insoluble in MeCN, the pure product could be afforded without silica gel column purification. In addition, the prepared ammonium oxides are versatile building blocks for synthesizing functionalized pyrazole derivatives.

Synthesis of 1,3,5-Trisubstituted Pyrazoles and Hydrazones Using Fe3O4?CeO2 Nanocomposite as an Efficient Heterogeneous Nanocatalyst

Abstract: Pyrazoles and hydrazones, as two significant kinds of potentially bioactivecompounds, were produced with good to excellent yields by condensation ofβ-dicarbonyl compounds with hydrazines in aqueous media in the presence ofFe3O4?CeO2nanocomposite as an efficient heterogeneous nanocatalyst. The magneticnanocatalyst can readily be separated using an external magnet and reused atleast six times without significant loss in activity. The products werecharacterized by IR and 1H and13C NMR spectra.

Metal-Free Direct C–H Thiolation and Thiocyanation of Pyrazolones

Metal-free approach for direct C–H thiolation and thiocyanation of N-substituted pyrazolones with disulfides and thiocyanate salts, respectively, are developed. These reactions allow the C–S bond coupling to proceed effectively under mild conditions, providing useful and convenient methods for preparation of a series of 4-thio-substituted pyrazolone analogues, which have potential applications in organic, medicinal and material chemistry. Preliminary mechanistic investigation suggested that radical processes are likely to involve in these transformations.

Discovery of novel triazole-containing pyrazole ester derivatives as potential antibacterial agents

To develop new antibacterial agents, a series of novel triazole-containing pyrazole ester derivatives were designed and synthesized and their biological activities were evaluated as potential topoisomerase II inhibitors. Compound 4d exhibited the most potent antibacterial activity with Minimum inhibitory concentration (MIC) alues of 4 μg/mL, 2 μg/mL, 4 μg/mL, and 0.5 μg/mL against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli, and Salmonella gallinarum, respectively. The in vivo enzyme inhibition assay 4d displayed the most potent topoisomerase II (IC50 = 13.5 μg/mL) and topoisomerase IV (IC50 = 24.2 μg/mL) inhibitory activity. Molecular docking was performed to position compound 4d into the topoisomerase II active site to determine the probable binding conformation. In summary, compound 4d may serve as potential topoisomerase II inhibitor.