51543-40-9

Basic information

• Product Name: (R)-2-Flurbiprofen
• Synonyms: (R)-2-Fluoro-α-methyl-1,1'-biphenyl-4-acetic acid;(R)-α-Methyl-2-fluoro-1,1'-biphenyl-4-acetic acid;(R)-(-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid (Flurbiprofe;[1,1'-Biphenyl]-4-aceticacid, 2-fluoro-a-Methyl-,(aR)-;Flurizan;MPC 7869;(R)-(-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid 97%;(R)-Flurbiprofen, >=99%
• CAS NO: 51543-40-9
• Molecular Formula: C₁₅H₁₃FO₂
• Molecular Weight: 244.26
• EINECS: 257-264-7
• Product Categories: API;Pharmaceutical ingredients
• Mol File: 51543-40-9.mol
• Article Data: 72

Chemical Properties

• Melting Point: 110-113 °C(lit.)
• Boiling Point: 376.2 °C at 760 mmHg
• Flash Point: 181.3 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.199 g/cm³
• Vapor Pressure: 2.84mmHg at 25°C
• Refractive Index: 1.34
• PKA: 4.14±0.10(Predicted)
• CAS DataBase Reference: (R)-2-Flurbiprofen(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Flurbiprofen(51543-40-9)
• EPA Substance Registry System: (R)-2-Flurbiprofen(51543-40-9)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 51543-40-9(Hazardous Substances Data)

Usage

Description

(R)-2-Flurbiprofen, also known as (R)-Flurbiprofen, is the R-isomer of Flurbiprofen (F598700), a non-selective COX inhibitor with diverse biological activities. It exhibits COX-inactivity but demonstrates significant effects on various biological processes, including the inhibition of γ-secretase activity, reduction of amyloid-β peptide formation, and suppression of tumor cell growth.

Uses

Used in Pharmaceutical Industry:
(R)-2-Flurbiprofen is used as an anti-inflammatory agent for its analgesic properties. It is particularly effective in reducing inflammation and pain through COX-independent mechanisms.
Used in Alzheimer's Disease Research:
(R)-2-Flurbiprofen is used as a potential therapeutic agent for Alzheimer's disease. It inhibits γ-secretase activity, leading to a reduction in the formation of amyloid-β peptide 1-42 (Aβ42), which is a key factor in the development of Alzheimer's disease. Additionally, it improves axonal transport in young Aβ-plaque free mice, although its effectiveness is limited in old mice with existing Aβ plaques.
Used in Cancer Research:
(R)-2-Flurbiprofen is used as an inhibitor of prostate tumor cell growth in vitro by inducing p75NTR protein expression. It also reduces tumor growth and metastasis in multiple mouse models of intestinal neoplasia, showcasing its potential as a therapeutic agent in cancer treatment.
Used in Inflammation Research:
(R)-2-Flurbiprofen is used as an inhibitor of NF-kB and AP-1 activation in RAW 264.7 macrophages, which are key players in the inflammatory response. It reduces paw edema in a rat model of zymosan-induced inflammation, highlighting its potential in treating inflammatory conditions through COX-independent pathways.

Biochem/physiol Actions

gamma secretase inhibitor; amyloid Abeta 42 lowering agent

InChI:InChI=1/C12H4F14/c13-7(9(15,16)17,10(18,19)20)5-1-2-6(4-3-5)8(14,11(21,22)23)12(24,25)26/h1-4H

Upstream product

• 113544-32-4 (S)-3-O-(2-(2-fluoro-4-biphenyl)propionyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 113544-38-0 methyl 2-(2-fluoro-4-biphenylyl)propionate 
• 5104-49-4 fluorobiprofen 
• 67-56-1 methanol 
• 189130-24-3 (2S)-2-(2-fluoro-biphenyl-4-yl)-propan-1-ol 
• 621-76-1 tripropyl orthoformate 
• 42771-82-4 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid 
• 111-87-5 octanol 
• 64-17-5 ethanol 
• 62784-66-1 bis(1-naphthyl)methanol 
• 76319-57-8 (S)-(+)-flurbiprofen, (S)-1-phenylethylamine salt 
• 82859-87-8 C₁₉H₂₁FO₂ 
• 71-36-3 butan-1-ol 
• 90500-55-3 (±)-methyl 2-(4-amino-3-fluorophenyl)propanoate 

Downstream Products

• 5104-49-4 fluorobiprofen 
• 5104-49-4 (R)-flurbiprofen 
• 1394164-75-0 5′-(S)-[(2-Fluoro-1,1′-biphenyl-4-yl)propanoyl]-thymidine 
• 5104-49-4 (S)-(+)-flurbiprofen 
• 1394164-76-1 5′-(R)-[(2-Fluoro-1,1′-biphenyl-4-yl)propanoyl]-thymidine 
• 52807-12-2 2-(2-fluoro-4'-hydroxy-biphenyl-4-yl)-propionic acid 
• 1130608-93-3 (R)-2-(2-fluoro-biphenyl-4-yl)-N-(3-{3-[4-(3-{3-[2-(2-fluoro-biphenyl-4-yl)-(R)-propionylamino]-propylamino}-propylamino)-3,6-dioxo-cyclohexa-1,4-dienylamino]-propylamino}-propyl)-propionamide 

Relevant articles and documents

An efficient method for the synthesis of (S)-flurbiprofen by 1,2-rearrangement of the aryl group

(S)-Flurbiprofen (1) is a nonsteroidal anti-inflammatory drug (NSAID) used to relieve pain and inflammation associated with osteoarthritis. Herein a new and practical method for the preparation of 1 from 4-bromo-2-fluorobiphenyl (2) is reported, which achieves a good overall yield (20%) and high enantioselectivity (96%). This method avoids the use of expensive catalysts and affords the possibility of large-scale manufacturing with simple operations.

Deracemization through photochemical E/Z isomerization of enamines

Catalytic deracemization of a-branched aldehydes is a direct strategy to construct enantiopure a-tertiary carbonyls, which are essential to pharmaceutical applications. Here, we report a photochemical E/Z isomerization strategy for the deracemization of a-branched aldehydes by using simple aminocatalysts and readily available photosensitizers. A variety of racemic a-branched aldehydes could be directly transformed into either enantiomer with high selectivity. Rapid photodynamic E/Z isomerization and highly stereospecific iminium/enamine tautomerization are two key factors that underlie the enantioenrichment. This study presents a distinctive photochemical E/Z isomerization strategy for externally tuning enamine catalysis.

Preparation method of flurbiprofen

The invention relates to the technical field of medicine synthesis, in particular to a preparation method of flurbiprofen, which comprises the following steps: carrying out Sonogashira coupling reaction on 4-bromo-2-fluorobiphenyl and trimethylsilylacetylene under the catalysis of palladium to obtain 4-trimethylsilylethynyl-2-fluorobiphenyl, removing trimethylsilyl from the product in an alkaline solution without separation, so as to obtain 4-ethynyl-2-fluorobiphenyl; and then taking a complex formed by nickel and a phosphine ligand in situ as a catalyst, taking formic acid as a carboxylation and hydrogenation reagent, carrying out hydrocarboxylation-hydrogenation cascade reaction on the 4-ethynyl-2-fluorobiphenyl, and conducting purifying to obtain flurbiprofen. The method has the advantages of easily available raw material sources, short route, simple operation, mild reaction conditions and high yield. According to the present invention, ethynyl is directly converted into a propionic acid group through the efficient one-pot cascade reaction, and the racemic flurbiprofen, the levorotatory flurbiprofen and the dextrorotatory flurbiprofen can be synthesized only by changing the phosphine ligand type, such that the preparation of the optical pure flurbiprofen through the tedious and low-efficiency splitting of the racemic flurbiprofen is avoided.