23979-41-1

Usage

Uses

Used in Pharmaceutical Industry:
(R)-NAPROXEN is used as an anti-inflammatory agent for the treatment of various conditions such as arthritis, tendinitis, bursitis, and other musculoskeletal disorders. It works by inhibiting the cyclooxygenase enzyme, which is responsible for the production of prostaglandins that cause inflammation, pain, and fever.
Used in Pain Management:
(R)-NAPROXEN is used as a pain reliever for mild to moderate pain, including menstrual cramps, dental pain, and headaches. Its anti-inflammatory and analgesic properties make it an effective option for managing pain and discomfort.
Used in Cyclooxygenase Inhibition:
(R)-NAPROXEN is used as a cyclooxygenase inhibitor for the prevention of blood clot formation and the reduction of inflammation. This application is particularly useful in the management of conditions that involve excessive inflammation, such as rheumatoid arthritis and osteoarthritis.

InChI:InChI=1/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m1/s1

Upstream product

• 113544-34-6 (R)-2-(6-Methoxy-naphthalen-2-yl)-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 
• 113544-31-3 (R)-3-O-(2-(6-methoxy-2-naphthyl)propionyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 54656-96-1 (S)-1-(4-pyridyl)ethanol 
• 52344-67-9 2-(6-methoxynaphthalene-2-yl)propionic anhydride 
• 27854-88-2 (R)-1-(4-pyridinyl)ethanol 
• 32305-59-2 S-2-(6-methoxy-2-naphthyl)propionaldehyde 
• 23981-80-8 naproxen 
• 622-40-2 2-(morpholin-4-yl)ethanol 
• 27602-79-5 2-(6-methoxynaphth-2-yl)acrylic acid 
• 84890-25-5 (R)-6-methoxy-α-methyl-2-naphthaleneacetic acid ethyl ester 
• 75-09-2 dichloromethane 
• 748801-45-8 (S)-2-(1-(6-methoxynaphthalen-2-yl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 362523-40-8 tert-butyl α-(6-methoxy-naphthalen-2-yl)acetate 
• 74-88-4 methyl iodide 

Downstream Products

• 112828-15-6 R-naproxen β-1-O-acyl-glucuronide 
• 1173289-41-2 (R)-N-(4-hydroxyphenethyl)-2-(6-methoxynaphthalen-2-yl)propanamide 
• 57849-23-7 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 57849-23-7 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 51072-36-7 (+)-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 1569315-13-4 (R)-4-methoxybenzyl-2-(6-methoxynaphthalen-2-yl)propanoate 
• 38835-18-6 (+)-naproxen acid chloride 
• 1416002-37-3 (S)-(2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxyphenyl)ethyl)(R)-(2-(6-methoxynaphthalen-2-yl)propanoate) 
• 1416002-36-2 (R)-((R)-2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxyphenyl)ethyl) 2-(6-methoxynaphthalen-2-yl)propanoate 
• 1416002-35-1 (R,S)-(2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxyphenyl)ethyl)(R)-2-(6-methoxynaphthalen-2-yl)propanoate 
• 1342344-03-9 methyl (S)-2-(6-methoxy-3-phenylnaphthalen-2-yl)propanoate 
• 1342343-91-2 (S)-2-(6-methoxy-3-phenylnaphthalen-2-yl)propanoic acid 
• 1280541-43-6 (S)-phenylephrine-(R)-naproxen 
• 1280541-42-5 (R)-phenylephrine-(R)-naproxen 

Relevant academic research and scientific papers

SYNTHESIS OF OPTICALLY ACTIVE 2-ARYLALKANOIC ACIDS BY THE USE OF 1,2-REARRANGEMENT OF THE ARYL GROUP

A new route to the synthesis of optically active 2-arylalkanoic acids was accomplished by using stereospecific 1,2-rearrangement of the aryl group in chiral 1-aryl-2-sulfonyloxy-1-alkanone acetals.

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.

Preparation of One-Pot Immobilized Lipase with Fe3O4 Nanoparticles Into Metal-Organic Framework For Enantioselective Hydrolysis of (R,S)-Naproxen Methyl Ester

Immobilization of enzyme to magnetic metal-organic frameworks (MOF) can preserve biological functionality in harsh environments to increase enzymes activity, stability, and improve reusability. The magnetic Fe3O4 nanoparticles were treated with calix[4]arene tetracarboxylic acid (Calix) and Candida rugosa lipase (CRL), and then encapsulated into the zeolitic imidazole framework-8 (Fe3O4@Calix-ZIF-8@CRL). The lipase activity data of Fe3O4@Calix-ZIF-8@CRL was 2.88 times higher than that of the Fe3O4@ZIF-8@CRL (without Calix). The catalytic properties of immobilized lipases were studied on the enantioselective hydrolysis of R/S-naproxen methyl ester. It was also observed that Fe3O4@Calix-ZIF-8@CRL has excellent enantioselectivity (E=371) compared to Fe3O4@ZIF-8@CRL (E=131). Furthermore, Fe3O4@Calix-ZIF-8@CRL was seen to still retain 30 % of the conversion rate after the fifth reuse. This work may also be useful for the pharmaceutical industry due to the increased reusability and stability of enzymes, the enantiomeric selectivity exhibited by MOF-enzyme biocomposites, and the significant differences in the biological activities of the enantiomers.

Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides

An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities. The reaction is tolerant of a variety of functional groups, and the resulting products can be converted to pharmaceutically-relevant chiral building blocks. A multivariate linear regression model was developed to quantitatively relate the influence of the α-chloroester substrate and ligand on enantioselectivity.

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.

Deracemizing α-Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis-Silyl Ketene Acetals with Water or Methanol

We report a highly enantioselective catalytic protonation of bis-silyl ketene acetals. Our method delivers α-branched carboxylic acids, including nonsteroidal anti-inflammatory arylpropionic acids such as Ibuprofen, in high enantiomeric purity and high yields. The process can be incorporated in an overall deracemization of α-branched carboxylic acids, involving a double deprotonation and silylation followed by the catalytic asymmetric protonation.

Enantioselective Palladium-Catalyzed Cross-Coupling of α-Bromo Carboxamides and Aryl Boronic Acids

We herein report an enantioselective palladium-catalyzed cross-coupling between α-bromo carboxamides and aryl boronic acids, generating a series of chiral α-aryl carboxamides in good yields and excellent enantioselectivities. The development of a chiral P,P=O ligand was critical in overcoming the second transmetalation issue and allows the first asymmetric palladium-catalyzed coupling of α-bromo carbonyl compounds.

Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides

The first iron-catalysed enantioselective Suzuki-Miyaura coupling reaction has been developed. In the presence of catalytic amounts of FeCl2 and (R,R)-QuinoxP?, lithium arylborates are cross-coupled with tert-butyl α-bromopropionate in an enantioconvergent manner, enabling facile access to various optically active α-arylpropionic acids including several nonsteroidal anti-inflammatory drugs (NSAIDs) of commercial importance. (R,R)-QuinoxP? is specifically able to induce chirality when compared to analogous P-chiral ligands that give racemic products, highlighting the critical importance of transmetalation in the present asymmetric cross-coupling system.

Structural insights into the ene-reductase synthesis of profens

Reduction of double bonds of α,β-unsaturated carboxylic acids and esters by ene-reductases remains challenging and it typically requires activation by a second electron-withdrawing moiety, such as a halide or second carboxylate group. We showed that profen precursors, 2-arylpropenoic acids and their esters, were efficiently reduced by Old Yellow Enzymes (OYEs). The XenA and GYE enzymes showed activity towards acids, while a wider range of enzymes were active towards the equivalent methyl esters. Comparative co-crystal structural analysis of profen-bound OYEs highlighted key interactions important in determining substrate binding in a catalytically active conformation. The general utility of ene reductases for the synthesis of (R)-profens was established and this work will now drive future mutagenesis studies to screen for the production of pharmaceutically-active (S)-profens.

Surface-mounted MOF templated fabrication of homochiral polymer thin film for enantioselective adsorption of drugs

A self-polymerized chiral monomer 3,4-dihydroxy-l-phenylalanine (l-DOPA) has been introduced into the pores of an achiral surface-mounted metal organic framework (SURMOF), and then the homochiral poly(l-DOPA) thin film has been successfully formed after UV light irradiation and etching of the SURMOF. Remarkably, such a poly(l-DOPA) thin film exhibited enantioselective adsorption of naproxen. This study opened a SURMOF-templated approach for preparing porous polymer thin films.