26510-95-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a synthetic intermediate for the production of 2-(carboethoxy)-3-(4′-bromo)phenylquinoxaline 1,4-dioxide, which has potential applications in the development of pharmaceuticals, particularly those targeting specific biological pathways or receptors.
Used in Chemical Synthesis:
In the field of organic chemistry, 3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER serves as a valuable building block for the synthesis of a wide range of organic compounds, including those with potential applications in various industries such as pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is also utilized in research and development settings to explore its reactivity, properties, and potential applications in the creation of new molecules and materials with specific functions or improved performance.

InChI:InChI=1/C11H11BrO3/c1-2-15-11(14)7-10(13)8-3-5-9(12)6-4-8/h3-6H,2,7H2,1H3

Upstream product

• 99-90-1 para-bromoacetophenone 
• 105-58-8 Diethyl carbonate 
• 623-73-4 diazoacetic acid ethyl ester 
• 1122-91-4 4-bromo-benzaldehyde 
• 141-97-9 ethyl acetoacetate 
• 313225-01-3 (1H-benzo[d][1,2,3]triazol-1-yl)(4-bromophenyl)methanone 
• 70-11-1 α-bromoacetophenone 
• 623-53-0 ethyl methyl carbonate 
• 623-00-7 4-bromobenzenecarbonitrile 
• 105-36-2 ethyl bromoacetate 
• 586-76-5 4-Bromobenzoic acid 
• 105-39-5 chloroacetic acid ethyl ester 
• 6148-64-7 ethyl potassium malonate 
• 82892-00-0 N-(4-bromobenzoyl)imidazole 

Downstream Products

• 100116-20-9 3-(4-bromo-phenyl)-3-thiosemicarbazono-propionic acid ethyl ester 
• 914222-57-4 2-(4-bromo-phenyl)-quinolin-4-ol 
• 63131-19-1 C₁₆H₂₂BrO₄PS₂ 
• 63131-17-9 C₁₆H₂₂BrO₃PS₂ 
• 81729-04-6 ethyl α-p-bromobenzoylcinnamate 
• 116404-03-6 Diethyl 2,4-di(p-bromobenzoyl)-3-(p-methoxyphenyl)pentanedioate 
• 116342-20-2 5-(p-bromophenyl)-5-hydroxy-3-methyl-2,4-diethoxycarbonylcyclohexanone 
• 878480-30-9 2-(4-bromobenzoyl)pent-4-enoic acid ethyl ester 
• 65939-88-0 2-(4-Bromo-phenyl)-4,5-dioxo-4,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester 
• 502841-11-4 3-bromo-2-(4-bromo-phenyl)-quinolin-4-ol 
• 179943-32-9 ethyl 3-(4-bromophenyl)-2-(hydroxyimino)-3-oxopropanoate 

Relevant academic research and scientific papers

Synthesis of 4-cyano pyrroles via mild Knorr reactions with β-ketonitriles

Mild methods for conducting Knorr chemistry with β-ketonitriles were developed. This enabled the preparation of 4-cyanopenta-substituted pyrroles and gave access to α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor potentiators for biol

Organic photovoltaics of diketopyrrolopyrrole copolymers with unsymmetric and regiorandom configuration of the side units

Diketopyrrolopyrrole (DPP) is a representative electron acceptor incorporated into narrow-bandgap polymers for organic photovoltaic cells (OPV). Commonly, identical aromatic units are attached to the sides of the DPP unit, forming symmetric DPP polymers. Herein we report the synthesis and characterization of DPP copolymers consisting of unsymmetric configurations of the side aromatics. The unsymmetric DPP copolymer with thienothiophene and benzene side moieties exhibits good solubility owing to the twisted dihedral angle at benzene and regiorandom configuration. A significant shallowing of the highest occupied molecular orbital level is observed in accordance with the electron-donating nature of the side units (benzene, thiophene, and thienothiophene). The overall power conversion efficiencies of the unsymmetric DPPs (2.3-2.4%) are greater than that of the centrosymmetric analogue (0.45%), which is discussed in view of bulk heterojunction morphology, polymer crystallinity, and space-charge-limited current mobilities. This comparative study highlights the effect of unsymmetric design on the molecular stacking and OPV performance of DPP copolymers.

Electrochemical Oxidative Cyclization: Synthesis of Polysubstituted Pyrrole from Enamines

A conceptually novel method for the preparation of pyrrole is described by electrochemical-oxidation-induced intermolecular annulation via enamines. In a simple undivided cell, based on a sodium acetate-facilitated, polysubstituted pyrrole derivations has been facilely synthesized under external oxidant-free condition. This electrosynthetic approach providing an environmentally benign protocol for C?C bond cross-coupling and oxidative annulation, which features unparalleled broad scope of substrates and practicality.

Construction of isoxazolone-fused phenanthridinesviaRh-catalyzed cascade C-H activation/cyclization of 3-arylisoxazolones with cyclic 2-diazo-1,3-diketones

A Rh(iii)-catalyzed cascade C-H activation/intramolecular cyclization of 3-aryl-5-isoxazolones with cyclic 2-diazo-1,3-diketones was described, leading to the formation of isoxazolo[2,3-f]phenanthridine skeletons. The protocol features the simultaneous one-pot formation of two new C-C/C-N bonds and one heterocycle in moderate-to-good yields with good functional group compatibility. It is amenable to large-scale synthesis and further transformation.

Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes

A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.

Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of Racemic β’-Keto-β-Amino Esters via Dynamic Kinetic Resolution

An iridium/f-diaphos catalytic system for the enantioselective hydrogenation of α-substituted β-ketoesters via dynamic kinetic resolution is reported. The desired anti β’-hydroxy-β-amino esters were obtained in moderate to good yields (60–95%) with 72–99% ees and 91:9 to 99:1 drs. This protocol tolerates various functional groups and could be easily conducted on gram scale with lower catalyst loading (TON up to 9100). (Figure presented.).

Promising new inhibitors of tyrosyl-DNA phosphodiesterase I (Tdp 1) combining 4- arylcoumarin and monoterpenoid moieties as components of complex antitumor therapy

Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is an important DNA repair enzyme in humans, and a current and promising inhibition target for the development of new chemosensitizing agents due to its ability to remove DNA damage caused by topoisomerase 1 (Top1) poisons such as topotecan and irinotecan. Herein, we report our work on the synthesis and characterization of new Tdp1 inhibitors that combine the arylcoumarin (neoflavonoid) and monoterpenoid moieties. Our results showed that they are potent Tdp1 inhibitors with IC50 values in the submicromolar range. In vivo experiments with mice revealed that compound 3ba (IC50 0.62 μM) induced a significant increase in the antitumor effect of topotecan on the Krebs-2 ascites tumor model. Our results further strengthen the argument that Tdp1 is a druggable target with the potential to be developed into a clinically-potent adjunct therapy in conjunction with Top1 poisons.

Radical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing N-Heterocycles via Dual Cobaloxime and Photoredox Catalysis

Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive molecules. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermolecular cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole products in satisfactory yields. In the presence of external alkenes, the tandem reaction generates E-selective coupling products with excellent chemo- and stereoselectivity.

An efficient route for the synthesis of N-(1H-benzo[d]imidazol-2-yl)benzamide derivatives promoted by CBr4 in one pot

A metal-free one-pot method for the synthesis of N-(1H-benzo[d]imidazol-2-yl)benzamide derivatives was proposed mediated by CBr4. The reaction went through ring formation and opening processes with only two protons leaving and the thermodynamically favorable products were selectively formed in moderate to good yields.

Design, Synthesis, and Biochemical Characterization of Non-Native Antagonists of the Pseudomonas aeruginosa Quorum Sensing Receptor LasR with Nanomolar IC50 Values

Quorum sensing (QS), a bacterial cell-to-cell communication system mediated by small molecules and peptides, has received significant interest as a potential target to block infection. The common pathogen Pseudomonas aeruginosa uses QS to regulate many of its virulence phenotypes at high cell densities, and the LasR QS receptor plays a critical role in this process. Small molecule tools that inhibit LasR activity would serve to illuminate its role in P. aeruginosa virulence, but we currently lack highly potent and selective LasR antagonists, despite considerable research in this area. V-06-018, an abiotic small molecule discovered in a high-throughput screen, represents one of the most potent known LasR antagonists but has seen little study since its initial report. Herein, we report a systematic study of the structure-activity relationships (SARs) that govern LasR antagonism by V-06-018. We synthesized a focused library of V-06-018 derivatives and evaluated the library for bioactivity using a variety of cell-based LasR reporter systems. The SAR trends revealed by these experiments allowed us to design probes with 10-fold greater potency than that of V-06-018 and 100-fold greater potency than other commonly used N-acyl-l-homoserine lactone (AHL)-based LasR antagonists, along with high selectivities for LasR. Biochemical experiments to probe the mechanism of antagonism by V-06-018 and its analogues support these compounds interacting with the native ligand-binding site in LasR and, at least in part, stabilizing an inactive form of the protein. The compounds described herein are the most potent and efficacious antagonists of LasR known and represent robust probes both for characterizing the mechanisms of LuxR-type QS and for chemical biology research in general in the growing QS field.