Tarenflurbil

Base Information

• Chemical Name: Tarenflurbil
• CAS No.: 51543-40-9
• Molecular Formula: C₁₅H₁₃FO₂
• Molecular Weight: 244.265
• Hs Code.: 2916399090
• European Community (EC) Number: 257-264-7
• NSC Number: 685699
• UNII: 501W00OOWA
• DSSTox Substance ID: DTXSID40199508
• Nikkaji Number: J261.753F
• Wikipedia: Tarenflurbil
• Wikidata: Q849769
• NCI Thesaurus Code: C26666
• Pharos Ligand ID: THHVGUZBP5BU
• Metabolomics Workbench ID: 55959
• ChEMBL ID: CHEMBL190083
• Mol file: 51543-40-9.mol

Synonyms:flurizan;MPC-7869;MPC7869;tarenflurbil;TMP-001;TMP001

Chemical Property of Tarenflurbil

Chemical Property:

• Vapor Pressure: 2.84mmHg at 25°C
• Melting Point: 110-113 °C(lit.)
• Refractive Index: 1.34
• Boiling Point: 376.2 °C at 760 mmHg
• PKA: 4.14±0.10(Predicted)
• Flash Point: 181.3 °C
• PSA: 37.30000
• Density: 1.199 g/cm³
• LogP: 3.68080
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 244.08995782
• Heavy Atom Count: 18
• Complexity: 286

Purity/Quality:

99% ^*data from raw suppliers

Flurizan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)O
• Isomeric SMILES: C[C@H](C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)O
• Recent ClinicalTrials: Bioavailability, Pharmacokinetics and Tissue Distribution of R-flurbiprofen Capsules in Healthy Subjects
• Recent EU Clinical Trials: TMP001 in relapsing-remitting multiple sclerosis: a multicentre open, baseline-controlled phase IIa clinical trial
• Description: (R)-Flurbiprofen is a COX-inactive enantiomer of the racemic non-selective COX inhibitor flurbiprofen that has diverse biological activities. It inhibits γ-secretase activity in vitro and, in vivo, it reduces formation of amyloid-β peptide 1-42 (Aβ42) and improves axonal transport in young Aβ-plaque free mice but not old mice with existing Aβ plaques in the Tg2576 transgenic model of Alzheimer''s disease. (R)-Flurbiprofen inhibits NF-kB activation and DNA binding as well as AP-1 DNA binding in RAW 264.7 macrophages and reduces paw edema in a rat model of zymosan-induced inflammation via COX-independent inhibition of NF-κB and AP-1 activation when administered at doses of 1, 3, and 9 mg/kg. It also suppresses prostate tumor cell growth in vitro by inducing p75NTR protein expression and reduces tumor growth and metastasis in multiple mouse models of intestinal neoplasia.
• Uses: (R)-2-Flurbiprofen is the R-isomer of Flurbiprofen (F598700), an anti-inflammatory used as an analgesic.

Technology Process of Tarenflurbil

There total 179 articles about Tarenflurbil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-(2-fluoro-biphenyl-4-yl)-acrylic acid → (R)-flurbiprofen (5104-49-4,51543-38-5,51543-39-6,51543-40-9)

Guidance literature:

With C₅₄H₇₂IrNP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen; caesium carbonate; In methanol; at 45 ℃; for 0.25h; under 4500.45 Torr; Pressure; Glovebox;

Reference yield: 90.0%

formic acid (64-18-6) + 3-fluoro-4-phenyl-1-ethynylbenzene → (R)-flurbiprofen (5104-49-4,51543-38-5,51543-39-6,51543-40-9)

Guidance literature:

With (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)benzene; bis(acetylacetonate)nickel(II); acetic anhydride; triethylamine; In 1,4-dioxane; at 70 ℃; for 24h; Inert atmosphere; Sealed tube;

Reference yield: 88.0%

(S)-(+)-1,1-diphenyl-3-(3-fluoro-4-phenylphenyl)-1-butene → (R)-flurbiprofen (5104-49-4,51543-38-5,51543-39-6,51543-40-9)

Guidance literature:

With sodium periodate; ruthenium trichloride; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 1.5h;

DOI:10.1021/ol702261t

upstream raw materials:

(S)-3-O-(2-(2-fluoro-4-biphenyl)propionyl)-1,2-O-isopropylidene-α-D-glucofuranose

methyl 2-(2-fluoro-4-biphenylyl)propionate

fluorobiprofen

methanol

Downstream raw materials:

2-(2-fluoro-4'-hydroxy-biphenyl-4-yl)-propionic acid

fluorobiprofen

(R)-flurbiprofen

(S)-(+)-flurbiprofen

Refernces

• 1、 Fu, Kaiyue,Ma, Yu,Sun, Yaxin,Tang, Bo,Yang, Guang,Yang, Peng,Yue, Jieyu,Zhang, Li,Zhou, Jianrong Steve. "Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel-Catalyzed Cascade Reactions: Facile Synthesis of Profens". supporting information. . Retrieved 2021/11/22.
• 2、 Guan, Zheng-Hui,Ren, Zhi-Hui,Wang, Yuan,Yang, Hui-Yi,Yao, Ya-Hong,Zou, Xian-Jin. "Palladium-Catalyzed Asymmetric Markovnikov Hydroxycarbonylation and Hydroalkoxycarbonylation of Vinyl Arenes: Synthesis of 2-Arylpropanoic Acids". supporting information. p. 23117 - 23122. Retrieved 2021/09/18.