33167-21-4

Usage

Uses

Used in Chemical Synthesis:
3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reagent/reactant for oxidative cross-coupling via dioxygen activation with indoles. This application allows for the formation of new chemical bonds and the creation of complex molecular structures.
Used in Pharmaceutical Industry:
3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reactant in the chlorination and hydrosilylation process for the synthesis of α-hydroxy β-amino acid derivatives. These derivatives are essential building blocks in the development of various pharmaceutical compounds.
Used in Chiral Lewis Base-Catalyzed Reduction:
3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER serves as a precursor for substrates in chiral Lewis base-catalyzed stereoselective reduction with trichlorosilane and water. This application is crucial for obtaining specific enantiomers, which are important in the pharmaceutical industry for their targeted therapeutic effects.
Used in Organic Synthesis:
3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reactant in intramolecular cyclization reactions for the synthesis of dihydrofurans. These cyclic compounds are valuable intermediates in the synthesis of various organic molecules and natural products.
Used in Accelerating Reactions:
3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reactant to rate-accelerate Michael reactions, which are essential in the formation of carbon-carbon double bonds in various organic compounds.
Used in Oxidative Coupling:
3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reactant in cerium ammonium nitrate-mediated oxidative coupling reactions. This application is vital for the formation of new carbon-carbon bonds and the synthesis of complex organic molecules.

InChI:InChI=1/C11H11ClO3/c1-2-15-11(14)7-10(13)8-4-3-5-9(12)6-8/h3-6H,2,7H2,1H3

Upstream product

• 618-46-2 m-Chlorobenzoyl chloride 
• 105-36-2 ethyl bromoacetate 
• 99-02-5 3'-Chloroacetophenone 
• 105-58-8 Diethyl carbonate 
• 6148-64-7 ethyl potassium malonate 
• 64-17-5 ethanol 
• 535-80-8 3-chlorobenzoate 
• 42428-03-5 (3-chlorophenyl)(1H-imidazol-1-yl)methanone 
• 893643-63-5 2-(3-chloro-benzoyl)-3-oxo-butyric acid ethyl ester 

Downstream Products

• 36309-40-7 6-(3-chlorophenyl)-2-thiouracil 
• 51725-85-0 3-(3-chlorophenyl)isoxazol-5(4H)-one 
• 76519-46-5 2-Amino-6-(3-chloro-phenyl)-3H-pyrimidin-4-one 
• 1026608-91-2 2-(3-Chloro-benzoyl)-pentanedioic acid diethyl ester 
• 194466-59-6 2-(3'-Chlorophenyl)-7-methyl-pyrido[1,2-a]pyrimidin-4-one 
• 194466-61-0 2-(3'-Chlorophenyl)-6,8-dimethyl-pyrido[1,2-a]pyrimidin-4-one 
• 784202-24-0 ethyl 3-chloro-α-[(dimethylamino)methylene]-β-oxobenzenepropanoate 
• 805231-20-3 [2-(3-chlorophenyl)-[1,3]dioxolan-2-yl]acetic acid ethyl ester 
• 1026889-57-5 3-(3-chlorobenzoyl)-6-hydroxymethyl-2-oxo-2H-1-benzopyran-2-one 
• 51699-45-7 (S)-(-)-1-(3'-Chlorophenyl)-1,3-Propanediol 
• 936947-00-1 5-(3-chloro-phenyl)-2-naphthalen-2-yl-2,4-dihydro-pyrazol-3-one 
• 936947-75-0 5-bromo-3-(3-chloro-phenyl)-1-naphthalen-2-yl-1H-pyrazole 
• 883989-35-3 (4S)-4-(3-chlorophenyl)-2-(4-nitrophenoxy)-1,3,2-dioxaphosphinane-2-oxide 
• 632327-18-5 (R)-(+)-1-(3-chlorophenyl)-1,3-propanediol 

Relevant academic research and scientific papers

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.

Phosphoryl N - fatty acyl nucleoside analogues for treatment of viral hepatitis and liver cancer

The invention discloses a phosphoryl N-fatty acyl nucleoside analogue for treating viral hepatitis and liver cancer. The phosphoryl N-fatty acyl nucleoside analogue is characterized in that a nucleoside analogue is modified by a cyclophosphoryl group and

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.

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.

Synthesis and biochemical evaluation of lid-open D-amino acid oxidase inhibitors

Most of the known inhibitors of D-amino acid oxidase (DAAO) are small polar molecules recognized by the active site of the enzyme. More recently a new class of DAAO inhibitors has been disclosed that interacts with loop 218?224 at the top of the binding pocket. These compounds have a significantly larger size and more beneficial physicochemical properties than most reported DAAO inhibitors, however, their structure-activity relationship is poorly explored. Here we report the synthesis and evaluation of this type of DAAO inhibitors that open the lid over the active site of DAAO. In order to collect relevant SAR data we varied two distinct parts of the inhibitors. A systematic variation of the pendant aromatic substituents according to the Topliss scheme resulted in DAAO inhibitors with low nanomolar activity. The activity showed low sensitivity to the substituents investigated. The variation of the linker connecting the pendant aromatic moiety and the acidic headgroup revealed that the interactions of the linker with the enzyme were crucial for achieving significant inhibitory activity. Structures and activities were analyzed based on available X-ray structures of the complexes. Our findings might support the design of drug-like DAAO inhibitors with advantageous physicochemical properties and ADME profile.

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.

Substituted phenyl pyrazolone derivatives and preparation and application (by machine translation)

The present invention provides a substituted phenyl pyrazolone derivatives, in particular to a 2 - phenyl - pyrazoline - 3 - ketone compound and its pharmaceutically acceptable salt, solvate. The substituted acetic acid ethyl ester with sodium hydroxide in aqueous solution in the [...] reflux reaction, then in the palladium-carbon and hydrogen under the action of the hydrogenolysis benzyl, phenyl [...] obtained, with the bromochlorodifluoromethane alkane reaction to obtain the chloro, finally with the secondary amine on the condensation to obtain the target compound. The invention substituted phenyl pyrazoline compounds in vitro exhibits excellent capability of eliminating the free radicals, and have more strongly inhibit H3 receptor activity, exhibits excellent penetration of the blood brain barrier capacity, has a unique dual active, therefore, its for cerebral apoplexy, Alzheimer's disease, Parkinson's disease, progressive neurodegenerative diseases such as frozen sickness treatment has a unique clinical effect. The compound of the invention for treating central system system related disease and inflammatory disease application of the medicament. The formula structure is as follows: (by machine translation)