5462-33-9

Usage

Uses

Used in Organic Synthesis:
2-(Phenylazo)acetoacetic acid ethyl ester is used as a reagent in organic synthesis for the preparation of various colored compounds. Its unique structure allows for the creation of a wide range of dyes and pigments, making it valuable in the development of new colorants for various applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(Phenylazo)acetoacetic acid ethyl ester is used as a building block for the synthesis of complex molecular structures. Its reactivity and the ability to form azo compounds make it a promising candidate for the development of new pharmaceutical agents, potentially contributing to the discovery of novel drugs with unique therapeutic properties.
Used in Chemical Industry:
2-(Phenylazo)acetoacetic acid ethyl ester is utilized in the chemical industry for the production of dyes and pigments. Its vibrant color properties and stability make it suitable for use in various applications, such as textiles, plastics, and paints, where colorfastness and resistance to fading are essential.
Used in Research and Development:
In research and development, 2-(Phenylazo)acetoacetic acid ethyl ester serves as a valuable tool for studying the properties and behavior of azo compounds. Its use in this context aids in understanding the underlying chemistry and potential applications of azo compounds, which can lead to advancements in various fields, including materials science and medicinal chemistry.

InChI:InChI=1/C12H14N2O3/c1-3-17-12(16)11(9(2)15)14-13-10-7-5-4-6-8-10/h4-8,11H,3H2,1-2H3/b14-13+

Upstream product

• 141-97-9 ethyl acetoacetate 
• 62-53-3 aniline 
• 100-34-5 benzene diazonium chloride 
• 2684-02-8 benzenediazonium 

Downstream Products

• 1747-61-1 2,3-dimethyl-4-phenylazoisoxazol-5-one 
• 78482-46-9 1-phenyl-3-carbomethoxy-4-(1H)pyridazinone 
• 344449-14-5 ethyl-5-cyano-1,6-dihydro-4-methyl-1-phenyl-6-oxopyridazine-3-carboxylate 
• 130103-09-2 2-[4-(3,5-Dimethyl-pyrazol-1-yl)-benzenesulfonyl]-5-methyl-4-phenylazo-2H-pyrazol-3-ol 
• 100517-71-3 2,6-dimethyl-5-phenylazo-3H-pyrimidin-4-one 
• 14985-77-4 6-methyl-5-phenylazo-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 98077-47-5 5-Methyl-4-phenylazo-2-(pyridine-2-carbonyl)-2,4-dihydro-pyrazol-3-one 
• 65996-60-3 4-oxo-1-phenyl-1,4-dihydropyridazine-3-carboxylic acid ethyl ester 
• 1333221-32-1 C₂₀H₁₇N₅O₃S 
• 1334629-49-0 7-methyl-5-oxo-6-(phenyldiazenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidine-2-sulfonamide 
• 78482-49-2 1-phenyl-3-carbohydrazide-4-(1H)-pyridazinone 
• 78482-48-1 5-phenylpyrazolo<4,3-c>pyridazin-3-(2H)one 
• 34165-60-1 2-Benzoyl-5-methyl-4-(phenyl-hydrazono)-2,4-dihydro-pyrazol-3-one 

Relevant academic research and scientific papers

Oxodihydropyridazine derivative and application thereof in antitumor drugs

The invention belongs to the technical field of drugs, and particularly relates to an oxodihydropyridazine derivative and application thereof in antitumor drugs. MTT results show that the oxodihydropyridazine derivative has the advantage of strong antitumor activity, and can be used for preparing antitumor drugs.

Oxodihydropyridazine derivative and application thereof in antitumor drugs

The invention belongs to the technical field of medicines, and particularly relates to oxodihydropyridazines and application thereof in antitumor drugs. MTT results show that the oxodihydropyridazinederivative has the advantage of high antitumor activity, and can be used for preparing antitumor drugs.

Discovery of [1,2,4]triazolo[4,3-a]pyrazine derivatives bearing a 4-oxo-pyridazinone moiety as potential c-Met kinase inhibitors

Two series of [1,2,4]triazolo[4,3-a]pyrazine derivatives bearing 4-oxo-pyridazinone moieties (compounds21a-land22a-l) were designed and their IC50values were evaluated against three cancer cell lines (A549, MCF-7 and HeLa) and c-Met kinase. Among them, the compound with most potential,22i,exhibited excellent anti-tumor activity against A549, MCF-7 and HeLa cancer cell lines with IC50values of 0.83 ± 0.07 μM, 0.15 ± 0.08 μM and 2.85 ± 0.74 μM, respectively, and it also possessed superior c-Met kinase inhibition ability at the nanomolar level (IC50= 48 nM). Moreover, dose-dependent experiments, AO fluorescence staining, cell cycle assay, Annexin V-FITC/PI staining and docking studies were carried out in this study. The results demonstrated that compound22icould be a potential c-Met kinase inhibitor.

Design, synthesis and biological evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing pyridazinone moiety as c-Met Inhibitors

Deregulation of the receptor tyrosine kinase mesenchymal epithelial transition factor (MET) has been implicated in several human cancers and is an attractive target for small molecule drug discovery. Herein, a series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing pyridazinone derivatives were designed, synthesized and evaluated for their enzymatic inhibitory activity against c-Met kinase and cellular potency against A549, HepG2, and MCF-7 cell lines. Eight of them are equal to more active than positive control Foretinib against one or more cell lines and enzyme. The most promising compound 53 showed superior activity to Foretinib, which possessed excellent c-Met kinase inhibition on a singledigital nanomolar level (IC50 = 0.6 nM), and cancer cells of A549 (IC50 = 0.003 μM), HepG2 (IC50 = 0.49 μM) and MCF-7 cells (IC50 = 0.006 μM). The result of AO single staining indicated that compound 53 could induce remarkable apoptosis of HepG2 cell.

A facile and rapid synthesis of benzothiazines

A series of 2H. 4H-2-[3-methyl-4-(substituted) phenyl azo pyrazolon-5-one-1-yl]-carbonyl methyl-3-oxo-1,4-benzothiazines have been synthesized by the reaction of 2H, 4H-2-hydrazino carbonyl methyl-3-oxo-1,4- benzothiazine with substituted acetoacetic ester derivatives using ultrasound and microwave irradiation. All the synthesized compounds were investigated for their antibacterial activities. The result indicated that the compounds showed convincing activities against Gram-positive bacteria (Bacillus subtilis and Streptococcus lactis) when compared with standard drug (ampicillin trihydrate). These compounds were also synthesized by conventional method and their structures have been elucidated on the basis of spectral analyses and chemical analysis.

Synthesis of 5-(substituted phenylazo)-6-hydroxy-4-methyl-3--cyano-2- pyridones from ethyl 3-oxo-2-(substituted phenylazo)butanoates

A new procedure for the synthesis of known azo pyridone dyes is presented. A series of 5-(substituted arylazo)-6-hydroxy-4-methyl-3-cyano-2--pyridones were prepared from ethyl 3-oxo-2-(substituted phenylazo)butanoates and cyanoacetamide in acetone using potassium hydroxide as a catalyst by simple refluxing the reaction mixture. The structure of these dyes was confirmed by FT-IR, NMR and UV-Vis spectroscopy. Copyright 2011 (CC) SCS.

Some Transition Metal Complexes Derived from the Heterocyclic Ligands 3-Methyl-4-Arylazopyrazole-5-Ones

Some planar and octahedral complexes of the sulphates of Cu(II) and Ni(II) with different 3-methyl-4-arylazo pyrazole-5-ones have been prepared.The complexes contain only one molecule of the ligand which functions as a bidentate donar coordinating through its carbonyl and azo group while the rest of the positions in the coordination geometry of metal are occupied by water molecules.The magnetic and electronic data of the complexes are discussed in the light of structures assigned.