52263-83-9

Usage

Uses

The R-enantiomer of the antiinflammatory drug Carprofen

Upstream product

• 99203-05-1 2-(6-Chloro-9H-carbazol-2-yl)-2-trimethylsilanyloxy-propionitrile 
• 71208-55-4 (6-chloro-2-carbazolyl)methylmalonic acid diethyl ester 
• 23592-74-7 2-acetylcarbazole 
• 99202-99-0 2-(1-acetoxyethyl)-6-chlorocarbazole 
• 70359-62-5 6-chloro-α-hydroxy-α-methylcarbazole-2-acetic acid 
• 53716-49-7 2-(6-chloro-carbazol-2-yl)-propionic acid 
• 52263-88-4 methyl (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate 
• 52262-89-2 ethyl 2-(6-chloro-9H-carbazol-2-yl)propanoate 
• 1402840-96-3 2-(6-chloro-9-(oxazol-4-ylcarbonyl)-9H-carbazol-2-yl)propanoic acid 
• 1402840-90-7 2-(6-chloro-9-(4-chlorobenzoyl)-9H-carbazol-2-yl)propanoic acid 
• 166408-09-9 benzyl 2-(3-chloro-9H-carbazol-7-yl)propionate 
• 1402841-02-4 (2R)-(6-chloro-9-(oxazol-4-ylcarbonyl)-9H-carbazol-2-yl)propanoic acid 
• 1402841-00-2 (2R)-(6-chloro-9-(4-chlorobenzoyl)-9H-carbazol-2-yl)propanoic acid 
• 1402840-86-1 benzyl 2-(6-chloro-9-(oxazol-4-ylcarbonyl)-9H-carbazol-2-yl)propanoate 

Relevant academic research and scientific papers

Lipase-Catalyzed Production of (S)-Carprofen Enhanced by Hydroxyethyl-β-cyclodextrins: Experiment and Optimization

Stereoselective resolution of (R,S)-carprofen methyl ester (CPOMe) by lipase-catalyzed hydrolysis to (S)-carprofen (CP) was investigated in an aqueous medium. With the highest catalytic activity, Candida antarctica Lipase A (CALA) was selected as catalyst compared with eight other lipases. Hydroxyethyl-β-cyclodextrin (HE-β-CD) was added to enhance the solubility of (R,S)-CPOMe, which significantly raised the conversion of substrate from 11.12% to 30.84%. Response surface methodology (RSM) was adopted to evaluate the influence of factors on the substrate conversion (c) and enantiomeric excess of product (eep), such as pH, concentrations of enzyme and HE-β-CD, temperature, substrate loading, and reaction time. The optimal conditions were obtained, including pH 6.0, 40 mg/mL CALA, 0.05 mmol substrate, 35 mmol/L HE-β-CD, agitation speed of 600 rpm, temperature of 76 °C, and reaction time of 30 h. Under the above conditions, (S)-CP as the desired product was obtained with an enantiomeric excess of 96.24% and overall conversion of 46.07%.

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.

Electrochemical Synthesis of Carbazoles by Dehydrogenative Coupling Reaction

A constant current protocol, employing undivided cells, a remarkably low supporting electrolyte concentration, inexpensive electrode materials, and a straightforward precursor synthesis enabling a novel access to N-protected carbazoles by anodic N,C bond formation using directly generated amidyl radicals is reported. Scalability of the reaction is demonstrated and an easy deblocking of the benzoyl protecting group is presented.

Total synthesis of carbazole alkaloids

A Suzuki-Miyaura cross coupling, followed by triphenylphosphine mediated Cadogan reductive cyclization sequence provided efficient access to a series of carbazole alkaloids. In the present work, this approach was applied to the total synthesis of mukonine, clauszoline K, koenoline, murrayanine, murrayafoline A, mukoeic acid, glycoborine, glycozolicine, mukolidine, mukoline, glycozoline, 3-methoxy-9H-carbazole-1-carboxylic acid methyl ester, (3-methoxy-9H-carbazol-1-yl)-methanol, 3-methoxy-9H-carbazole-1-carbaldehyde, 3-methoxy-9H-carbazole-1-carboxylic acid, 2-methyl-9H-carbazole and nonsteroidal anti-inflammatory drug (NSAID) carprofen and its derivatives.

Carprofen and its intermediate synthesis method

A synthesis of carprofen, (1) 2 - (3 - bromo - 4 - chlorophenyl) propionic acid and P-nitro aniline reaction, formula C - 1 as shown in the; (2) Type C - 1 as shown in the compound is subjected to reduction reaction, formula C - 2 as shown in the; (3) Type C - 2 shown compound is subjected to diazotization reaction, preparation formula B - 3 as shown in the and by-product B - 31 shown compound mixture; (4) Type B - 3 and the product of a compound represented by B - 31 shown compound mixture through processing formula B - 3 illustrated compound; (5) Type B - 3 as shown in the reaction shown in formula A carprofen;

Carprofen and its intermediate synthesis method

A synthesis of carprofen: (1) 4 - chloroaniline and 2 - iodo - 4 - bromo-chlorobenzene reaction, generating M - 1 illustrated compound. (2) Type M - 1 as shown in the after reaction, generating M - 2 shown compound. (3) Type M - 2 by the reaction of a compound of, formula M - 3 illustrated compound. (4) Type M - 3 through the reaction of a compound represented by formula M - 4 illustrated compound. (5) The formula M - 4 through the reaction of a compound represented by formula M - 5 illustrated compound. (6) Type M - 5 as shown in the reaction shown in formula A carprofen. .

Carprofen and its intermediate synthesis method

A synthesis of carprofen, comprising the following steps: (1) 2 - (3 - chloro - 4 - nitrophenyl) propionic acid and to P-chloroaniline reaction, formula A - 1 as shown in the; (2) Type A - 1 shown compound is subjected to reduction reaction, formula A - 2 illustrated compound; (3) Type A - 2 shown through the diazo coupling reaction compound, a compound represented by formula A preparation, and by-product A - 3 illustrated compound; (4) Steps (3) to obtain the compound of formula A shown and by-product A - 3 shown compound mixture through purification treatment, to obtain not comprising by-product A - 3 of formula A shown carprofen.

Carprofen and its intermediate synthesis method

A synthesis of carprofen: (1) 4 - [...] and 2 - chloro - 5 - bromophenyl reaction, generating M - 1 illustrated compound. (2) Type M - 1 as shown in the after reaction, generating M - 2 shown compound. (3) Type M - 2 by the reaction of a compound of, formula M - 3 illustrated compound. (4) Type M - 3 through the reaction of a compound represented by formula M - 4 illustrated compound. (5) The formula M - 4 through the reaction of a compound represented by formula M - 5 illustrated compound. (6) Type M - 5 as shown in the reaction shown in formula A carprofen. .

Diquats with Robust Chirality: Facile Resolution, Synthesis of Chiral Dyes, and Application as Selectors in Chiral Analysis

Diquats with extremely high racemization barriers with ΔG≠theor of 233 kJ mol?1 at 180 °C are described. Reported configurational robustness is due to a combination of two structural features: the rigid o-xylylene tether connecting the nitrogen atoms and the presence of two substituents in the bay region of the bipyridinium scaffold. The straightforward synthesis of diquats, plus facile resolution and derivatization make them attractive for chiral application studies. This is demonstrated by: 1) synthesis of the first non-racemic diquat dyes with pronounced chiroptical properties, and 2) capability of diquats to interact stereospecifically with chiral molecules. This suggests potential for diquat derivatives to be used as chiral selectors in separation methods.

Carbazole compound, and synthesis method and application of compound

The invention discloses a carbazole compound represented by a formula (2) and a synthesis method of the compound. A high-iodine salt is taken as a reaction raw material, and under the action of an inorganic nitrogen reagent, an additive, a base and a metal catalyst, a reaction is carried out in a solvent under a condition of 80-150 DEG C to obtain various carbazole compounds. According to the method provided by the invention, nitrogen atoms are introduced in a later period, so that the non-compatibility of nitrogen heterocyclic rings to the reaction conditions such as the metal catalyst and the like in an early reaction period is avoided. In addition, two aryl groups in the high-iodine salt are fully utilized, so that the atomic economic efficiency of the method provided by the present invention is fully exhibited. The carbazole compound prepared by the method provided by the invention can be further applied to the synthesis of non-steroidal anti-inflammatory drug carprofen.