Farglitazar

Base Information

• Chemical Name: Farglitazar
• CAS No.: 196808-45-4
• Molecular Formula: C34H30N2O5
• Molecular Weight: 546.623
• UNII: 3433GY7132
• DSSTox Substance ID: DTXSID1047310
• Nikkaji Number: J1.046.637G
• Wikipedia: Farglitazar
• Wikidata: Q5435087
• NCI Thesaurus Code: C81693
• Pharos Ligand ID: LHLLRS2GNH5N
• ChEMBL ID: CHEMBL107367
• Mol file: 196808-45-4.mol

Synonyms:farglitazar;GI 2570;GI 262570;GI-2570;GI-262570;GI2570;GI262570

Chemical Property of Farglitazar

Chemical Property:

• Vapor Pressure: 1.45E-26mmHg at 25°C
• Boiling Point: 793.7°C at 760 mmHg
• Flash Point: 433.8°C
• PSA: 101.66000
• Density: 1.257g/cm³
• LogP: 6.68330
• XLogP3: 7.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 546.21547206
• Heavy Atom Count: 41
• Complexity: 818

Purity/Quality:

99% ^*data from raw suppliers

N-(2-Benzoylphenyl)-O-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N=C(O1)C2=CC=CC=C2)CCOC3=CC=C(C=C3)CC(C(=O)O)NC4=CC=CC=C4C(=O)C5=CC=CC=C5
• Isomeric SMILES: CC1=C(N=C(O1)C2=CC=CC=C2)CCOC3=CC=C(C=C3)C[C@@H](C(=O)O)NC4=CC=CC=C4C(=O)C5=CC=CC=C5
• Recent ClinicalTrials: Antifibrotic Activity Of GI262570 In Chronic Hepatitis C Subjects
• Recent EU Clinical Trials: A double-blind, randomized, placebo-controlled multi-centre, phase II parallel dose-ranging study to assess the antifibrotic activity of GI262570 in chronic hepatitis C subjects with hepatic fibrosis who have failed prior antiviral therapy.
• Uses: Treatment of Type II diabetes (insulin action enhancer). Farglitazar is a peroxisome proliferator-activated receptor (PPAR) agonist and has been explored for treating hepatic fibrosis and type 2 diabetes.

Technology Process of Farglitazar

There total 11 articles about Farglitazar 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:

(2S)-<(2-benzoylphenyl)amino>-3-<4-<2-(5-methyl-2-phenyloxazol4-yl)ethoxy>phenyl>propionic acid methyl ester (196810-20-5) → farglitazar (196808-45-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; Ambient temperature;

DOI:10.1021/jm9804127

Reference yield:

2(S)-<(2-benzoylphenyl)amino>-3-<4-<2-(5-methyl-2-phenyl-3H-imidazol-4-yl)ethoxy>phenyl>propionic acid methyl ester (219598-15-9) → 2(S)-<(2-benzoylphenyl)amino>-3-<4-<2-(5-methyl-2-phenyl-3H-imidazol-4-yl)ethoxy>phenyl>propionic acid (196808-45-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 25 ℃; for 2.5h;

DOI:10.1021/jm980413z

Reference yield:

(5-methyl-2-phenyloxazol-4-yl)ethanol (103788-65-4) → farglitazar (196808-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / PPh₃, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature

2: 202 mg / 1.0 M aq. LiOH / tetrahydrofuran; methanol / Ambient temperature

With lithium hydroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol;

DOI:10.1021/jm9804127

upstream raw materials:

(2S)-<(2-benzoylphenyl)amino>-3-<4-<2-(5-methyl-2-phenyloxazol4-yl)ethoxy>phenyl>propionic acid methyl ester

L-Tyr-OMe

(5-methyl-2-phenyloxazol-4-yl)ethanol

(S)-2-<(2-benzoylphenyl)amino>-3-(4-hydroxyphenyl)propionic acid methyl ester

Downstream raw materials:

(S)-2-(2-Benzoyl-phenylamino)-N-((R)-1-hydroxymethyl-2-methyl-propyl)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionamide

(S)-2-(2-Benzoyl-phenylamino)-N-((R)-1-formyl-2-methyl-propyl)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionamide

Refernces

• 1、 Henke, Brad R.,Blanchard, Steven G.,Brackeen, Marcus F.,Brown, Kathleen K.,Cobb, Jeff E.,Collins, Jon L.,Harrington Jr., W. Wallace,Hashim, Mir A.,Hull-Ryde, Emily A.,Kaldor, Istvan,Kliewer, Steven A.,Lake, Debra H.,Leesnitzer, Lisa M.,Lehmann, Jürgen M.,Lenhard, James M.,Orband-Miller, Lisa A.,Miller, John F.,Mook Jr., Robert A.,Noble, Stewart A.,Oliver Jr., William,Parks, Derek J.,Plunket, Kelli D.,Szewczyk, Jerzy R.,Willson, Timothy M.. "N-(2-benzoylphenyl)-L-tyrosine PPARγ agonists. 1. Discovery of a novel series of potent antihyperglycemic and antihyperlipidemic agents". . p. 5020 - 5036. Retrieved 2007/10/03.