10565-18-1

Usage

Uses

Used in Pharmaceutical Industry:
2-(p-Nitrophenyl)acetoacetic acid ethyl ester is used as a key ingredient in the production of pharmaceuticals for its ability to contribute to the development of medications with anti-inflammatory and anti-ulcer effects. Its presence in these formulations aids in the management and treatment of various conditions that benefit from such therapeutic properties.
Used in Organic Synthesis:
In the field of organic chemistry, 2-(p-Nitrophenyl)acetoacetic acid ethyl ester is utilized as a pharmaceutical intermediate and a reagent for the synthesis of complex organic compounds. Its versatility in reactions allows for the creation of a diverse array of chemical entities, making it an indispensable component in the synthesis toolkit of chemists.
Used in Research and Development:
2-(p-Nitrophenyl)acetoacetic acid ethyl ester is also employed in research and development settings, where its properties are explored for potential new applications and to enhance existing ones. Its role in the discovery and innovation of novel pharmaceutical agents and organic compounds is of significant value to the scientific community.

Upstream product

• 141-97-9 ethyl acetoacetate 
• 100-00-5 4-chlorobenzonitrile 
• 623-73-4 diazoacetic acid ethyl ester 
• 100-19-6 (4-nitrophenyl)ethanone 
• 586-78-7 para-nitrophenyl bromide 
• 636-98-6 p-nitrobenzene iodide 

Downstream Products

• 1068515-28-5 3-methyl-4-(4-nitrophenyl)-1-(pyridin-2-yl)-1H-pyrazol-5-ol 
• 1160169-24-3 (Z)-ethyl 3-amino-2-(4-nitrophenyl)but-2-enoate 

Relevant academic research and scientific papers

Biaryl Formation in the Copper(I) Mediated Arylation of Stable Enolate Anions with o-Halogenonitrobenzenes

o-Bromo- and o-iodonitrobenzenes react with stable enolate anions in hot DMF in the presence of copper(I) iodide, to afford not the expected arylation products but the coupling products, 2,2'-dinitrobiphenyls.

Synthetic Scope of Br?nsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate

The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Br?nsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl-methyl ketones produced only aryl-migrated products, whereas other ketones yielded a mixture of products. For diaryl ketones, the identity of two inseparable migrated products was confirmed by two-dimensional NMR spectroscopy.

AMINO-ACID ANILIDES AS SMALL MOLECULE MODULATORS OF IL-17

The present invention relates to a compound according to formula I (I) and pharmaceutically acceptable salts, hydrates, or solvates thereof. The invention further relates to said compounds for use in therapy, to pharmaceutical compositions comprising said compounds, to methods of treating diseases, e.g. dermal diseases, with said compounds, and to the use of said compounds in the manufacture of medicaments.

DMT1 Inhibitors Kill Cancer Stem Cells by Blocking Lysosomal Iron Translocation

Cancer stem cells (CSC) constitute a cell subpopulation in solid tumors that is responsible for resistance to conventional chemotherapy, metastasis and cancer relapse. The natural product Salinomycin can selectively target this cell niche by directly interacting with lysosomal iron, taking advantage of upregulated iron homeostasis in CSC. Here, inhibitors of the divalent metal transporter 1 (DMT1) have been identified that selectively target CSC by blocking lysosomal iron translocation. This leads to lysosomal iron accumulation, production of reactive oxygen species and cell death with features of ferroptosis. DMT1 inhibitors selectively target CSC in primary cancer cells and circulating tumor cells, demonstrating the physiological relevance of this strategy. Taken together, this opens up opportunities to tackle unmet needs in anti-cancer therapy.

Metal-free arylation of ethyl acetoacetate with hypervalent diaryliodonium salts: An immediate access to diverse 3-aryl-4(1 H)-quinolones

A clean arylation protocol of ethyl acetoacetate was developed using hypervalent diaryliodonium salts under mild and metal-free conditions. The scope of the reaction, using symmetric and unsymmetric iodonium salts with varying sterics and electronics, was examined. Further, this method has been applied for the synthesis of antimalarial compound ELQ-300, which is currently in preclinical development.

Synthesis and biological evaluation of substituted pyrazoles as blockers of divalent metal transporter 1 (DMT1)

Three distinct series of substituted pyrazole blockers of divalent metal transporter 1 (DMT1) were elaborated from the high-throughput screening pyrazolone hit 1. Preliminary hit-to-lead efforts revealed a preference for electron-withdrawing substituents in the 4-amido-5-hydroxypyrazole series 6a-l. In turn, this preference was more pronounced in a series of 4-aryl-5- hydroxypyrazoles 8a-j. The representative analogs 6f and 12f were found to be efficacious in a rodent model of acute iron hyperabsorption. These three series represent promising starting points for lead optimization efforts aimed at the discovery of DMT1 blockers as iron overload therapeutics.

PYRAZOLE AND PYRROLE COMPOUNDS USEFUL IN TREATING IRON DISORDERS

This invention is directed to pyrazole and pyrrole compounds, for example, compounds of formula (I): wherein R1, R2, R3 and R4 are as defined herein, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment of iron disorders. This invention is also directed to pharmaceutical compositions comprising the compounds and methods of using the compounds to treat iron disorders.