14580-22-4

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-Chlorophenyl)-3-methyl-2-pyrazolin-5-one is used as an intermediate compound for the synthesis of 1-(2-chlorophenyl)-3-methylchromeno[2,3-c]pyrazol-4(1H)-one, a heterocyclic analog of xanthone. This analog may have potential applications in the development of new pharmaceuticals, particularly in the area of medicinal chemistry.
Used in Chemical Synthesis:
In the field of chemical synthesis, 1-(2-Chlorophenyl)-3-methyl-2-pyrazolin-5-one can be utilized as a building block for the creation of more complex molecules with specific properties. Its unique structure allows for further functionalization and modification, making it a valuable component in the synthesis of various organic compounds.
Used in Research and Development:
Due to its unique chemical properties and potential applications, 1-(2-Chlorophenyl)-3-methyl-2-pyrazolin-5-one may also be used in research and development for exploring new chemical reactions, understanding its reactivity, and identifying novel applications in various industries, including materials science, pharmaceuticals, and agrochemicals.

InChI:InChI=1/C10H9ClN2O/c1-7-6-10(14)13(12-7)9-5-3-2-4-8(9)11/h2-5H,6H2,1H3

Upstream product

• 89-25-8 edaravone 
• 95-51-2 o-chloroaniline 
• 41052-75-9 o-chlorophenylhydrazine hydrochloride 
• 141-97-9 ethyl acetoacetate 
• 10449-07-7 (2-chlorophenyl)hydrazine 

Downstream Products

• 67365-78-0 2-(2-chloro-phenyl)-4-furfurylidene-5-methyl-2,4-dihydro-pyrazol-3-one 
• 38839-68-8 2-(2-chloro-phenyl)-4-[4-(3-ethyl-3H-benzothiazol-2-ylidene)-3-phenyl-but-2-enylidene]-5-methyl-2,4-dihydro-pyrazol-3-one 
• 85094-16-2 1-(2-Chloro-phenyl)-3,4-dimethyl-1H-pyrano[2,3-c]pyrazol-6-one 
• 1057507-57-9 6-amino-4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(2-chlorophenyl)-4,5-dihydro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine 
• 679843-75-5 1-(2-chlorophenyl)-3-methyl-5-oxo-4,5-dihydropyrazole-4-carbaldehyde 
• 1415230-71-5 1-(2-chlorophenyl)-3-methyl-4-(3-oxobutyl)-1H-pyrazol-5-yl acetate 
• 1415230-95-3 4,4'-(1-(2-chlorophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-4,4-diyl)bis(butan-2-one) 
• 1415230-65-7 1-(2-chlorophenyl)-3-methyl-1H-pyrazol-5-yl acetate 
• 1438397-48-8 4,4'-[(1-allyl-quinolin-2-one)methylene]bis[3-methyl-1-(2-chlorophenyl)-1H-pyrazol-5-ol] 
• 1438397-56-8 1-allyl-3-(3,5-dimethyl-1,7-bis(2-chlorophenyl)-1,4-dihydro-1H-dipyrazolo[3,4-b:4'3'-e]pyran-4-yl)quinoline-2-one 
• 1438397-40-0 1-allyl-3-{(Z)-[1-(2-chlorophenyl)-3-methyl-1,5-dihydro-4H-pyrazol-5-one-4-ylidene]methyl}quinolin-2(1H)-one 
• 1438397-44-4 1-allyl-7-chloro-3-{(Z)-[1-(2-chlorophenyl)-3-methyl-1,5-dihydro-4H-pyrazol-5-one-4-ylidene]methyl}quinolin-2(1H)-one 
• 1438397-52-4 4,4'-[(1-allyl-7-chloroquinolin-2-one)methylene]bis[3-methyl-1-(2-chlorophenyl)-1H-pyrazol-5-ol] 
• 1438397-60-4 1-allyl-7-chloro-3-(3,5-dimethyl-1,7-bis(2-chlorophenyl)-1,4-dihydro-1H-dipyrazolo[3,4-b:4'3'-e]pyran-4-yl)quinoline-2-one 

Relevant academic research and scientific papers

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.

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.

Synthesis of pyrazolones and pyrazoles via Pd-catalyzed aerobic oxidative dehydrogenation

A palladium-catalyzed oxidative dehydrogenation reaction in the presence of AMS and base to synthesize pyrazolones and pyrazoles was identified. This method can be utilized to a wide range of substrates, operates under mild react conditions and can give high yields. We believe it could be used as an alternative protocol for the classical dehydrogenation reactions.

Copper-catalyzed acylation of pyrazolones with aldehydes to afford 4-acylpyrazolones

Copper-catalyzed direct acylation of the alkenyl C-H bond in 1,2-dihydro-3H-pyrazol-3-ones has been developed, affording a series of 4-acylpyrazolones in moderate to good yields. Notably, this protocol involves readily accessible substrates and reagents, which have good functional group tolerance leading to pyrazolone derivatives under mild reaction conditions.

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.

Copper/Persulfate-Promoted Oxidative Decarboxylative C?H Acylation of Pyrazolones with α-Oxocarboxylic Acids: Direct Access to 4-Acylpyrazolones under Mild Conditions

A facile and efficient oxidative C?H acylation of N-substituted pyrazolones using α-oxocarboxylic acids as an acyl group source was developed. A combination of Cu(OAc)2 and K2S2O8 enables the reaction to proceed smoothly under air and provides a wide array of 4-acylpyrazolone products in moderate to excellent yields. The mechanism of this transformation is believed to proceed via a copper-induced decarboxylation to form the acyl-copper species. This method provides a convenient and useful route for a direct installation of an acyl moiety into bioactive pyrazolone derivatives, which can be further utilized in many applications. (Figure presented.).

Palladium N-heterocyclic carbene catalyzed regioselective C-H halogenation of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones using N-halosuccinimides (NXS)

A novel palladium N-heterocyclic carbene [Pd(NHC)Cl2] complex of vitamin B1 was synthesized and characterized by 1H NMR, EDX, FT-IR and UV-visible spectroscopy. The complex was used as a catalyst for regioselective ortho-C-H chlorination/bromination of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones via C-H bond activation utilizing Ag2O as the effective terminal additive. The catalyst was easy to prepare, efficient and found to be highly regioselective, affording the target products in moderate to excellent yields.

A facile organocatalyzed Michael addition of pyrazolines to α,β-unsaturated carbonyl compounds

A new highly efficient cascade reaction of pyrazolines with α,β-unsaturated carbonyl compounds catalyzed by DBU was reported. The process underwent the first deprotection/Michael addition reaction to give 4-substituted pyrazoline derivatives, which were further converted into 4,4-di-substituted pyrazolone derivatives through the second deprotection/Michael reaction. The mechanism for this reaction was also studied.

N,N-Dialkyl-N′-chlorosulfonyl chloroformamidines in heterocyclic synthesis. part IX.* novel triazolo-fused thiatriazoles and pyrazolo-fused oxathiazines

N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted with 4-substituted urazoles 2 to give [1,2,4]triazolo[1,2-b] [1,2,3,5]thiatriazoles 3 in a selective 1,2-NN dinucleophilic mode of reaction.The reaction of 1 with N1-substituted pyrazol-5-ones 4 afforded pyrazolo[4,3-e][1,4,3] oxathiazines 5 via selective 1,3-CCO dinucleophilic substitution. Compounds 3 and 5 were the sole products isolated from the respective reactions and both represent new ring systems. CSIRO 2010.

DRUGS COMPRISING COMBINATION OF ANTITHROMBOTIC AGENT WITH PYRAZOLONE DERIVATIVE

It is intended to provide drugs for treating and/or preventing ischemic diseases which are safe and have little side effects. Namely, drugs comprising a combination of an antithrombotic agent and a pyrazolone derivative defined in the description or its pharmaceutically acceptable salt.