28059-69-0

Usage

Uses

Used in Chemical Synthesis:
2-(4-Nitrophenoxy)-Propanoic Acid Ethyl Ester is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, facilitating the creation of diverse molecules with potential applications in different industries.
Used in Smiles' Rearrangement:
In the field of organic chemistry, 2-(4-Nitrophenoxy)-Propanoic Acid Ethyl Ester is used as a key reactant in the Smiles' rearrangement on borohydride reduction of nitrophenoxy esters. This reaction is significant for the synthesis of complex organic molecules, particularly those with rearranged structures that can be further modified for specific applications.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2-(4-Nitrophenoxy)-Propanoic Acid Ethyl Ester may also find applications in the pharmaceutical industry. Its ability to participate in various chemical reactions could make it a valuable building block for the development of new drugs or drug candidates, particularly those targeting specific biological pathways or receptors.
Used in Research and Development:
2-(4-Nitrophenoxy)-Propanoic Acid Ethyl Ester is also likely to be used in research and development settings, where chemists and scientists explore its reactivity and potential applications in creating new compounds with specific properties. This can lead to the discovery of novel materials or substances with improved performance in various applications, such as in the fields of materials science, pharmaceuticals, or even environmental science.

Upstream product

• 824-78-2 4-nitrophenol sodium salt 
• 535-11-5 Ethyl 2-bromopropionate 
• 1124-31-8 potassium 4-nitrophenolate 
• 100-02-7 4-nitro-phenol 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 6111-99-5 ethyl diazoalaninate 

Downstream Products

• 13794-10-0 (RS)-2-(4-nitrophenoxy)propionic acid 
• 28059-75-8 ethyl 2-(4-aminophenoxy)propionate 
• 28059-71-4 2-(4-nitrophenoxy)propanol 
• 28059-73-6 2-(4-Acetamidophenoxy)propanol 

Relevant academic research and scientific papers

Design and synthesis of novel quinazolinone-based fibrates as PPARα agonists with antihyperlipidemic activity

Aiming to discover new antihyperlipidemic agents, a new set of quinazolinone-fibrate hybrids 9a–r bearing the essential features for peroxisome proliferator-activated receptor-α (PPARα) agonistic activity was synthesized and the structures were confirmed by different spectral data. All the target compounds were screened for their PPARα agonistic activity. Compounds 9o and 9q exhibited potent activity, with EC50 values better than that of fenofibrate by 8.7- and 27-fold, respectively. Molecular docking investigations were performed for all the newly synthesized compounds in the active site of the PPARα receptor to study their interactions and energies in the receptor. Moreover, the antihyperlipidemic and antioxidant activities of compounds 9o and 9q were determined using Triton WR-1339-induced hyperlipidemic rats. Compound 9q exhibited effective hypolipidemic activity in a dose-dependent manner, where it significantly reduced the serum levels of total cholesterol, triglycerides, low-density lipoprotein cholesterol, and very-low-density lipoprotein cholesterol and increased the level of high-density lipoprotein cholesterol. Furthermore, it possesses a powerful antioxidant profile where it significantly elevated the levels of reduced glutathione as well as the total antioxidant capacity and significantly decreased the malondialdehyde level. The histopathological studies revealed that compound 9q improved the aortic architecture and hepatic steatosis. These findings support that compound 9q could be a promising lead compound for the development of new antihyperlipidemic agents.

Supramolecularly regulated copper-bisoxazoline catalysts for the efficient insertion of carbenoid species into hydroxyl bonds

The catalytic insertion of copper carbenoids into O-H bonds affords synthetically useful α-alkyl/aryl-α-alkoxy/aryloxy derivatives. Herein, the design, preparation and application of supramolecularly regulated copper(i) complexes of bisoxazoline ligands is reported. We have demonstrated that the catalytic performance of these systems can be modulated by the use of an external molecule (i.e.the regulation agent), which interacts with a polyethyleneoxy chain on the ligand (i.e.the regulation site)viasupramolecular interactions. This approach has been applied to an array of structurally diverse alcohols (cycloalkyl, alkyl and aryl derivatives). Moreover, we have used this methodology to synthesise advanced synthetic intermediates of biologically relevant compounds.

Structure-based modification of carbonyl-diphenylpyrimidines (Car-DPPYs) as a novel focal adhesion kinase (FAK) inhibitor against various stubborn cancer cells

A family of carbonyl-substituted diphenylpyrimidine derivatives (Car-DPPYs) with strong activity against focal adhesion kinase (FAK), were described in this manuscript. Among them, compounds 7a (IC50 = 5.17 nM) and 7f (IC50 = 2.58 nM) displayed equal anti-FAK enzymatic activity to the lead compound TAE226 (6.79 nM). In particular, compound 7a also exhibited strong antiproliferative activity against several stubborn cancer cells, including AsPC-1 cells (IC50 = 0.105 μM), BxPC-3 cells (IC50 = 0.090 μM), and MCF-7/ADR cells (IC50 = 0.59 μM). Additionally, compound 7a also showed great antitumor efficacy in vivo via aAsPC-1 cancer Xenograft mouse model. The preliminary mechanism study by Western blot analysis revealed that 7a repressed FAK phosphorylation in AsPC cancer cells. Taken together, the results indicate that compound 7a may serve as a promising preclinical candidate for treatment of stubborn cancers.

Optical resolution of aryloxypropionic acids and their esters by HPLC on cellulose tris-3,5-dimethyl-triphenylcarbamate derivative

Chiral chromatographic resolution of a series of antiphlogistic 2- aryloxypropionic acids and their methyl and ethyl esters was performed using a Chiralcel OD column. The CSP selected resolved most of the acids and esters efficiently, the enantiomers being well separated without requiring time consuming analysis. Chromatographic separation of R enriched samples was performed to determine the correct elution order. Using eluting systems such as hexane and 2-propanol, or hexane, 2-propanol and formic acid, the S enantiomer of all acids and esters was always found to elute first. We also considered the role of electron-donating or electron-withdrawing substituents (at the aryloxylic moiety) on the chiral resolution. It was shown that the electronic features of the substituents have more influence on the chiral interactions between the solutes and the CSP than their steric hindrance. Finally we determined, by molecular models, the interaction between CSP and solutes. In this way were able to determine all the potential sites for interactions, which are compatible with the conformations of the compounds and the structure of the stationary phase, and point out those interactions which enable chiral resolution.