21575-91-7

Usage

Uses

Used in Pharmaceutical Industry:
3-(3-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reactant for the synthesis of various pharmaceutical compounds with different therapeutic applications. Its ability to be incorporated into complex molecular structures makes it a valuable asset in the development of new drugs.
Used in the Synthesis of Aroylbenzoxepinones:
3-(3-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reactant for the synthesis of aroylbenzoxepinones, which are known for their analgesic activity. These compounds have the potential to be developed into effective pain-relieving medications.
Used in the Synthesis of (Heteroaryl)(carboxamido)arylpyrrole Derivatives:
3-(3-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is also used in the synthesis of (heteroaryl)(carboxamido)arylpyrrole derivatives, which exhibit Cdc7 kinase inhibitory activity. Inhibiting Cdc7 kinase has been shown to have potential applications in cancer therapy, as it plays a role in the regulation of DNA replication and cell cycle progression.
Used in the Synthesis of Cambinol Analogs:
3-(3-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reactant in the synthesis of cambinol analogs, which are known for their sirtuin inhibition and antitumor activity. Sirtuins are a family of proteins that have been implicated in various cellular processes, including aging and cancer. Inhibiting sirtuins with cambinol analogs may provide a new approach to cancer treatment.
Used in the Synthesis of TunePhos-type Diphosphine Ligands:
3-(3-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is also used in the synthesis of TunePhos-type diphosphine ligands, which are utilized in asymmetric hydrogenation reactions. Asymmetric hydrogenation is an important technique in the pharmaceutical industry for the production of enantiomerically pure compounds, which are essential for the development of many drugs with improved efficacy and reduced side effects.

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

Upstream product

• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 105-58-8 Diethyl carbonate 
• 24398-88-7 ethyl 3-bromobenzoate 
• 141-78-6 ethyl acetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 3132-99-8 m-bromobenzoic aldehyde 
• 95-92-1 oxalic acid diethyl ester 
• 585-76-2 m-bromobenzoic acid 
• 6148-64-7 ethyl potassium malonate 
• 91240-83-4 1-(3-bromo-benzoyl)-1H-imidazole 
• 51699-41-3 ethyl 3-hydroxy-3-(3-bromophenyl)-propanoate 
• 1711-09-7 3-bromobenzoyl chloride 
• 811467-20-6 ethyl-2-diazo-3-hydroxy-3-(3-bromophenyl)-propanoate 

Downstream Products

• 96722-98-4 5-(3-Bromo-phenyl)-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-3,4-dicarboxylic acid diethyl ester 
• 96723-00-1 5-(3-Bromo-phenyl)-1-(3-chloro-phenyl)-1H-pyrazole-3,4-dicarboxylic acid diethyl ester 
• 96722-99-5 5-(3-Bromo-phenyl)-1-m-tolyl-1H-pyrazole-3,4-dicarboxylic acid diethyl ester 
• 895524-55-7 ethyl 2-(3-bromobenzoyl)-3-(dimethylamino)acrylate 
• 1325713-81-2 (Z)-ethyl 3-(allylamino)-3-(3-bromophenyl)acrylate 
• 1325714-23-5 ethyl 2-(3-bromophenyl)-4-formyl-1H-pyrrole-3-carboxylate 
• 1629162-01-1 (R)-benzyl 1-(3-bromophenyl)-3-tert-butyl-4-oxo-2,3-diazaspiro[4.4]nona-1,7-diene-7-carboxylate 
• 1629161-84-7 3-(3-bromophenyl)-1-tert-butyl-1H-pyrazol-5(4H)-one 
• 2142-63-4 1-(3-Bromophenyl)ethanone 

Relevant academic research and scientific papers

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.

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.).

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.

Double Enzyme-Catalyzed One-Pot Synthesis of Enantiocomplementary Vicinal Fluoro Alcohols

A double-enzyme-catalyzed strategy for the synthesis of enantiocomplementary vicinal fluoro alcohols through a one-pot, three-step process including lipase-catalyzed hydrolysis, spontaneous decarboxylative fluorination, and subsequent ketoreductase-catalyzed reduction was developed. With this approach, β-ketonic esters were converted to the corresponding vicinal fluoro alcohols with high isolated yields (up to 92percent) and stereoselectivities (up to 99percent). This new cascade process addresses some issues in comparison with traditional methods such as environmentally hazardous reaction conditions and low stereoselectivity outcome.

Desymmetrization of meso-dicarbonatecyclohexene with β-Hydrazino carboxylic esters via a Pd-catalyzed allylic substitution cascade

The desymmetrization of meso-dicarbonatecyclohexene with β-hydrazino carboxylic esters has been achieved via a RuPHOX/Pd-catalyzed allylic substitution cascade for the construction of chiral hexahydrocinnoline derivatives with high performance. Mechanistic studies reveal that the reaction exploits a pathway different from that of our previous work and that the first nitrogen nucleophilic process is the rate-determining step. The protocol could be conducted on a gram scale without any loss of catalytic behavior, and the corresponding chiral hexahydrocinnolines can undergo diverse transformations.

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

Development of 2-arylbenzo[: H] quinolone analogs as selective CYP1B1 inhibitors

The CYP1B1 enzyme is regarded as a potential target for cancer prevention and therapy. Based on the structure of α-naphthoflavone (ANF), diverse 2-arylbenzo[h]quinolone derivatives were designed, synthesized and evaluated as selective CYP1B1 inhibitors. Compared with ANF, although few of the title compounds possessed comparable or slightly higher CYP1B1 inhibitory activity, these compounds displayed a significantly increased selectivity toward CYP1B1 over CYP1A2. Among them compounds 5e, 5g and 5h potently inhibited the activity of CYP1B1 with IC50 values of 3.6, 3.9 and 4.1 nM respectively, paralleled by an excellent selectivity profile. On the basis of predicted clogP values, these target compounds may exhibit improved water-solubility compared to ANF. In particular, 5h showed a great superiority in the reversal of CYP1B1-mediated docetaxel resistance in vitro. The current study may serve as a good starting point for the further development of more potent as well as specific CYP1B1 inhibitors capable of reversing CYP1B1-mediated anticancer-drug resistance.

In situ generation of nitrile oxides from copper carbene and tert -butyl nitrite: Synthesis of fully substituted isoxazoles

Herein, we present a novel [3 + 2] cycloaddition reaction of β-keto esters with nitrile oxides, which were generated in situ from copper carbene and tert-butyl nitrite. This three-component reaction provides new methodology for the direct synthesis of fully substituted isoxazole derivatives, featuring mild reaction conditions, readily accessible starting materials and simple operation. The experimental studies and DFT calculations suggest that the reaction starts with the generation of the key intermediate nitrile oxides, followed by a [3 + 2] cycloaddition reaction of β-keto esters to give the final isoxazole products.

Bromide-Mediated C-H Bond Functionalization: Intermolecular Annulation of Phenylethanone Derivatives with Alkynes for the Synthesis of 1-Naphthols

Bromide-mediated intermolecular annulation of phenylethanone derivatives with alkynes has been developed, which allows for the regioselective formation of polysubstituted 1-naphthols. The usage of readily available bromine catalyst, broad substrate scope, and mild conditions make this protocol very practical. Mechanistic investigations reveal that the bromination of phenylethanone derivatives occurs to yield bromo-substituted intermediates, which react in situ with alkynes to furnish the desired 1-naphthols.

Enantioselective Synthesis of 3,5,6-Substituted Dihydropyranones and Dihydropyridinones using Isothiourea-Mediated Catalysis

The scope of dihydropyranone and dihydropyridinone products accessible by isothiourea-catalyzed processes has been expanded and explored through the use of 2-N-tosyliminoacrylates and 2-aroylacrylates in a Michael addition-lactonization/lactamization cascade reaction. Notably, to ensure reproducibility it is essential to use homoanhydrides as ammonium enolate precursors with 2-aroyl acrylates, while carboxylic acids can be used with 2-N-tosyliminoacrylates, delivering a range of 3,5,6-substituted dihydropyranones and dihydropyridinones with high enantioselectivity (typically >90 % ee). The derivatization of the heterocyclic core of a 3,5,6-substituted dihydropyranone through hydrogenation is also reported.