51146-57-7

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-Ibuprofen is used as a precursor in the synthesis of the active (S)-isomer of Ibuprofen, which is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic, antipyretic, and anti-inflammatory properties. The (S)-isomer is responsible for the majority of the drug's therapeutic effects.
Used in Research Applications:
(R)-(-)-Ibuprofen is used as a research tool to study the differences in biological activity and metabolism between the (R) and (S) enantiomers of Ibuprofen. This helps in understanding the stereoselectivity of drug action and the potential for developing enantiomer-specific drugs with improved safety and efficacy profiles.
Used in Lipid Metabolism Studies:
(R)-(-)-Ibuprofen is used in research to investigate its role in lipid metabolism, as it is incorporated into triglycerides along with fatty acids. This can provide insights into the potential use of (R)-Ibuprofen or its derivatives in the development of therapies targeting lipid-related disorders.
Used in Inflammation and Immune Response Research:
(R)-(-)-Ibuprofen is used in studies to explore its potential effects on NF-κB activation, superoxide formation, β-glucuronidase release, and LTB4 generation by stimulated neutrophils. This can contribute to the understanding of its role in modulating inflammation and immune responses, which may lead to the development of new therapeutic strategies for inflammatory and immune-related diseases.

InChI:InChI=1/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m1/s1

Upstream product

• 201230-82-2 carbon monoxide 
• 63444-56-4 p-isobutylstyrene 
• 15687-27-1 ibuprofen 
• 61566-34-5 (+/-)-ibuprofen methyl ester 
• 121839-78-9 (2R)-2-[4-(2-methylpropyl)phenyl]propanamide 
• 85711-18-8 1-isobutyl-4-[(R)-1-methylallyl]benzene 
• 85711-17-7 1-isobutyl-4-[(S)-1-methylallyl]benzene 
• 113544-36-8 (R)-2-(4-Isobutyl-phenyl)-propionic acid (3aR,5R,6S,6aR)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 113544-28-8 (R)-3-O-(2-(4-isobutylphenyl)propionyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 123054-56-8 2-(4-Isobutyl-phenyl)-propionic acid (S)-1,2-dimethyl-propyl ester 
• 123054-49-9 2-(4-Isobutyl-phenyl)-propionic acid (R)-methoxycarbonyl-phenyl-methyl ester 
• 123054-51-3 (S)-2-[2-(4-Isobutyl-phenyl)-propionyloxy]-succinic acid dimethyl ester 
• 123054-45-5 2-(4-Isobutyl-phenyl)-propionic acid (S)-1-methoxycarbonyl-ethyl ester 
• 123054-42-2 2-(4-Isobutyl-phenyl)-propionic acid (S)-1-ethoxycarbonyl-ethyl ester 

Downstream Products

• 121734-80-3 (R)-2-(4-Isobutyl-phenyl)-N-((S)-1-phenyl-ethyl)-propionamide 
• 93469-76-2 3-hydroxy-2-(4-isobutyl-phenyl)-2-methyl-propionic acid 
• 593279-84-6 2-(4-isobutyl-phenyl)-N-pyridin-3-yl-propionamide 
• 593279-83-5 2-(4-isobutyl-phenyl)-N-pyridin-2-yl-propionamide 
• 81576-57-0 (R)-ibuprofen methyl ester 
• 266359-83-5 repertaxin 
• 354899-91-5 (S)-2-[(R)-2-(4-isobutylphenyl)propionylamino]propionic acid methyl ester 
• 114978-05-1 (R)-2-(4-isobutylphenyl)propionyl chloride 
• 59512-29-7 2-(4-isobutyl-phenyl)-N-phenyl-propionamide 

Relevant academic research and scientific papers

O 2-(N -Hydroxy(methoxy)-2-ethanesulfonamido) protected diazen-1-ium-1,2-diolates: Nitric oxide release via a base-induced β-elimination cleavage

O2-(Ethanesulfohydroxamic acid) and O2-(N-methoxy-2- ethanesulfonylamido) diazen-1-ium-1,2-diolates (4-7), a novel type of O 2-(protected) diazeniumdiolate, were synthesized using a key thioacetate oxidation reaction. Nitr

Reshaping the active pocket of esterase Est816 for resolution of economically important racemates

Bacterial esterases are potential biocatalysts for the production of optically pure compounds. However, the substrate promiscuity and chiral selectivity of esterases usually have a negative correlation, which limits their commercial value. Herein, an efficient and versatile esterase (Est816) was identified as a promising catalyst for the hydrolysis of a wide range of economically important substrates with low enantioselectivity. We rationally designed several variants with up to 11-fold increased catalytic efficiency towards ethyl 2-arylpropionates, mostly retaining the initial substrate scope and enantioselectivity. These variants provided a dramatic increase in efficiency for biocatalytic applications. Based on the best variant Est816-M1, several variants with higher or inverted enantioselectivity were designed through careful analysis of the structural information and molecular docking. Two stereoselectively complementary mutants, Est816-M3 and Est816-M4, successfully overcame and even reversed the low enantioselectivity, and several 2-arylpropionic acid derivatives with highEvalues were obtained. Our results offer potential industrial biocatalysts for the preparation of structurally diverse chiral carboxylic acids and further lay the foundation for improving the catalytic efficiency and enantioselectivity of esterases.

Bidentate phosphine-phosphine oxide ligand and intermediate, preparation method and application thereof

The invention discloses a bidentate phosphine-phosphine oxide ligand and an intermediate, a preparation method and application thereof. The phosphine oxide compound is shown as a formula I and/or ent-I. The phosphine oxide compound is used as a metal ligand and is applied to Suzuki-Miyaura coupling reaction so that generation of self-coupled by-products is avoided, and an alpha-aryl carbonyl compound is obtained; and the dosages of the ligand and the metal catalyst are less.

Homochiral Metal-Organic Frameworks for Enantioselective Separations in Liquid Chromatography

Selective separation of enantiomers is a substantial challenge for the pharmaceutical industry. Chromatography on chiral stationary phases is the standard method, but at a very high cost for industrial-scale purification due to the high cost of the chiral stationary phases. Typically, these materials are poorly robust, expensive to manufacture, and often too specific for a single desired substrate, lacking desirable versatility across different chiral analytes. Here, we disclose a porous, robust homochiral metal-organic framework (MOF), TAMOF-1, built from copper(II) and an affordable linker prepared from natural l-histidine. TAMOF-1 has shown to be able to separate a variety of model racemic mixtures, including drugs, in a wide range of solvents of different polarity, outperforming several commercial chiral columns for HPLC separations. Although not exploited in the present article, it is worthy to mention that the preparation of this new material is scalable to the multikilogram scale, opening unprecedented possibilities for low-energy chiral separation at the industrial scale.

Preparation and characterization of a new open-tubular capillary column for enantioseparation by capillary electrochromatography

In order to use the enantioseparation capability of cationic cyclodextrin and to combine the advantages of capillary electrochromatography (CEC) with open-tubular (OT) column, in this study, a new OT-CEC, coated with cationic cyclodextrin (1-allylimidazolium-β-cyclodextrin [AI-β-CD]) as chiral stationary phase (CSP), was prepared and applied for enantioseparation. Synthesized AI-β-CD was characterized by infrared (IR) spectrometry and mass spectrometry (MS). The preparation conditions for the AI-β-CD-coated column were optimized with the orthogonal experiment design L9(34). The column prepared was characterized by scanning electron microscopy (SEM) and elemental analysis (EA). The results showed that the thickness of stationary phase in the inner surface of the AI-β-CD-coated columns was about 0.2 to 0.5?μm. The AI-β-CD content in stationary phase based on the EA was approximately 2.77?mmol·m?2. The AI-β-CD-coated columns could separate all 14 chiral compounds (histidine, lysine, arginine, glutamate, aspartic acid, cysteine, serine, valine, isoleucine, phenylalanine, salbutamol, atenolol, ibuprofen, and napropamide) successfully in the study and exhibit excellent reproducibility and stability. We propose that the column, coated with AI-β-CD, has a great potential for enantioseparation in OT-CEC.

Colistin sulfate chiral stationary phase for the enantioselective separation of pharmaceuticals using organic polymer monolithic capillary chromatography ?

A new functionalized polymer monolithic capillary with a macrocyclic antibiotic, namely colistin sulfate, as chiral selector was prepared via the copolymerization of binary monomer mixtures consisting of glycidyl methacrylate (GMA) and ethylene glycol dimethacrylate (EGDMA) in porogenic solvents namely 1-propanol and 1,4-butanediol, in the presence of azobisiso-butyronitrile (AIBN) as initiator and colistin sulfate. The prepared capillaries were investigated for the enantioselective nano-LC separation of a group of racemic pharmaceuticals, namely, α- and β-blockers, anti-inflammatory drugs, antifungal drugs, norepinephrine-dopamine reuptake inhibitors, catecholamines, sedative hypnotics, antihistaminics, anticancer drugs, and antiarrhythmic drugs. Acceptable separation was achieved for many drugs using reversed phase chromatographic conditions with no separation achieved under normal phase conditions. Colistin sulfate appears to be useful addition to the available macrocyclic antibiotic chiral phases used in liquid chromatography.

Palladium-Catalyzed Enantioselective Thiocarbonylation of Styrenes

A highly enantioselective thiocarbonylation of styrenes with CO and thiols has been achieved by Pd catalysis, providing highly enantioenriched thioesters in good to excellent yields. Key to the successful execution of this reaction is the use of a chiral sulfoxide-(P-dialkyl)-phosphine (SOP) ligands. This thiocarbonylation proceeds smoothly under mild reaction conditions (1 atm CO and 0 °C) and displays broad substrate scope. Also demonstrated is that this transformation can be conducted using surrogates of CO, greatly increasing the safety aspects of running the reaction. The generality and utility of the method is manifested by its application to the synthetic transformations of thioester products and the direct acylation of cysteine-containing dipeptides. A primary mechanism was investigated and a plausible catalytic cycle was proposed.

Method for synthesizing thioester compounds through olefin insert carbonyl sulfide esterification (by machine translation)

The invention belongs to the field, and belongs to the field of chemical synthesis. The invention specifically relates to a method for synthesizing chiral or non-chiral thioester compounds through palladium-catalyzed olefin carbonyl sulfide esterification

Method for synthesizing alkyne through catalytic asymmetric cross coupling (by machine translation)

The invention belongs to the field of, asymmetric synthesis, and discloses a method for catalyzing asymmetric cross- coupling to synthesize: an alkyne, and the L method comprises, the following steps, of A: preparing B a cuprous, salt and C a: ligand; preparing a catalyst; adding a base; reacting the compound with the compound with the compound; and reacting the compound with the compound. Of these, one of them, X is selected from the group consisting of, R halogens. 1 Optionally substituted heteroarylsulfonylcyanamide groups selected from the, group consisting, of optionally substituted, phenyl groups In-flight vehicle, R6 Trialkyl silyl groups or alkyl radicals, R2 Cycloalkyl radicals optionally substituted with an, optionally substituted alkyl, (CH radical2 )n R4 Multi,layer chain, n＝0-10,R saw blade4 A group selected, from, the group consisting of phenyl, alkenyl, aralkynyls, noonyloxy,and, noonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylphenyl disiloxy-radicals. R3 A ligand, selected from hydrogen or any of the functional groups, is selected from the group consisting of, hydrogen and any L other functional group. The method, R disclosed by the, A invention has the, advantages of good catalytic, R ’ effect, wide application range. and high catalytic efficiency, and the, method disclosed by the, invention has the. advantages of good catalytic effect, wide application range and high catalytic efficiency. (by machine translation)

Synthesis of Chiral Esters via Asymmetric Wolff Rearrangement Reaction

The first asymmetric Wolff rearrangement reaction that directly converts α-diazoketones into broadly useful chiral α,α-disubstituted carboxylic esters with high enantioselectivities (up to 97.5:2.5 er) is reported. The cascade reaction proceeds through the seamless combination of visible-light-induced formation of the ketene intermediate and asymmetric ketene esterification using a readily available benzotetramisole-type catalyst.