Muraglitazar

Base Information

• Chemical Name: Muraglitazar
• CAS No.: 331741-94-7
• Molecular Formula: C29H28N2O7
• Molecular Weight: 516.551
• UNII: W1MKM70WQI
• DSSTox Substance ID: DTXSID9057719
• Nikkaji Number: J1.967.931D
• Wikipedia: Muraglitazar
• Wikidata: Q6937233
• NCI Thesaurus Code: C75190
• Pharos Ligand ID: N3WW99X1GYP9
• Metabolomics Workbench ID: 149812
• ChEMBL ID: CHEMBL186179
• Mol file: 331741-94-7.mol

Synonyms:BMS 298585;BMS-298585;BMS298585;muraglitazar;N-((4-methoxyphenoxy)carbonyl)-N-((4-(2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy)phenyl)methyl)glycine;Pargluva

Chemical Property of Muraglitazar

Chemical Property:

• Vapor Pressure: 9.11E-23mmHg at 25°C
• Melting Point: 123-125°C
• Refractive Index: 1.601
• Boiling Point: 736.4 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 399.2 °C
• PSA: 120.12000
• Density: 1.274 g/cm³
• LogP: 4.81940
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 12
• Exact Mass: 516.18965124
• Heavy Atom Count: 38
• Complexity: 730

Purity/Quality:

98%Min ^*data from raw suppliers

Muraglitazar ^*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)CN(CC(=O)O)C(=O)OC4=CC=C(C=C4)OC
• Recent ClinicalTrials: An Investigational Drug Co-Administered With Insulin in Patients With Type 2 Diabetes (0478-065)
• Description: Muraglitazar is a dual agonist of peroxisome proliferator-activated receptor α (PPARα) and PPARγ (EC50s = 0.32 and 0.11 μM, respectively). It is selective for PPARα/γ over other nuclear receptors, including PPARδ, RXRα, RARs, estrogen receptor α (ERα), ERβ, androgen receptor (AR), and progesterone receptor (PR). Muraglitazar (50 μM) reduces the size of lipid droplets in oleic acid-treated HepaRG human hepatocytes. It reduces plasma levels of glucose, triglycerides, free fatty acids, and insulin by 54, 33, 62, and 48%, respectively, in db/db mice when administered at a dose of 10 mg/kg per day. Muraglitazar (10 mg/kg per day) reduces plasma levels of glucose, triglycerides, and cholesterol in diet-induced obese mice. Muraglitazar also inhibits LPS-induced increases in nitric oxide (NO) production and IL-6, TNF-α, and inducible nitric oxide synthase (iNOS) protein levels in J774 murine macrophages in a concentration-dependent manner. It inhibits carrageenan-induced paw edema in mice when administered at doses ranging from 12.5 to 50 mg/kg.
• Uses: It is a peroxisome proliferator-activated receptor (PPAR) a/ dual agonist It is a peroxisome proliferator-activated receptor (PPAR) α/γ dual agonist.

Technology Process of Muraglitazar

There total 7 articles about Muraglitazar 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: 94.0%

N-[(4-methoxyphenoxy)carbonyl]-N-[[4-[2-(5-methyl-2-phenyl-4-oxazolyl)-ethoxy]phenyl]methyl]glycine methyl ester (331746-67-9) → muraglitazar (331741-94-7)

Guidance literature:

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

DOI:10.1021/jm0496436

Reference yield:

{[1-{4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-amino}-acetic acid methyl ester (951403-91-1) → muraglitazar (331741-94-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 4.48 g / NaBH₄ / methanol / 3.5 h / 0 - 25 °C

2: 98 percent / Et₃N / CH₂Cl₂ / 2 h / 25 °C

3: 94 percent / aq. LiOH / tetrahydrofuran / 2.5 h / 25 °C

With lithium hydroxide; sodium tetrahydroborate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm0496436

Reference yield:

{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]benzylamino}acetic acid methyl ester (331746-65-7) → muraglitazar (331741-94-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Et₃N / CH₂Cl₂ / 2 h / 25 °C

2: 94 percent / aq. LiOH / tetrahydrofuran / 2.5 h / 25 °C

With lithium hydroxide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm0496436

upstream raw materials:

N-[(4-methoxyphenoxy)carbonyl]-N-[[4-[2-(5-methyl-2-phenyl-4-oxazolyl)-ethoxy]phenyl]methyl]glycine methyl ester

{[1-{4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-amino}-acetic acid methyl ester

{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]benzylamino}acetic acid methyl ester

4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde

Refernces

• 1、 Devasthale, Pratik V.,Chen, Sean,Jeon, Yoon,Qu, Fucheng,Shao, Chunning,Wang, Wei,Zhang, Hao,Cap, Michael,Farrelly, Dennis,Golla, Rajasree,Grover, Gary,Harrity, Thomas,Ma, Zhengping,Moore, Lisa,Ren, Jimmy,Seethala, Ramakrishna,Cheng, Lin,Sleph, Paul,Sun, Wei,Tieman, Aaron,Wetterau, John R.,Doweyko, Arthur,Chandrasena, Gamini,Chang, Shu Y.,Humphreys, W. Griffith,Sasseville, Vito G.,Biller, Scott A.,Ryono, Denis E.,Selan, Fred,Hariharan, Narayanan,Cheng, Peter T. W.. "Design and synthesis of N-[(4-methoxyphenoxy)carbonyl]-N-[[4-[2-(5-methyl- 2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]glycine [muraglitazar/BMS-298585], a novel peroxisome proliferator-activated receptor α/γ dual agonist with efficacious glucose and lipid-l". . p. 2248 - 2250. Retrieved 2007/10/03.