Dimethyl 2-[[4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3-yl)ethoxy]phenyl]methyl]propanedioate

Base Information

• Chemical Name: Dimethyl 2-[[4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3-yl)ethoxy]phenyl]methyl]propanedioate
• CAS No.: 353280-43-0
• Molecular Formula: C28H25NO7S
• Molecular Weight: 519.575
• DSSTox Substance ID: DTXSID80433312
• Wikidata: Q82247436
• ChEMBL ID: CHEMBL4303501
• Mol file: 353280-43-0.mol

Synonyms:S26948

Chemical Property of Dimethyl 2-[[4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3-yl)ethoxy]phenyl]methyl]propanedioate

Chemical Property:

• PSA: 129.14000
• LogP: 3.87770
• Storage Temp.: Store at RT
• Solubility.: DMSO: soluble10mg/mL (clear solution)
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 12
• Exact Mass: 519.13517331
• Heavy Atom Count: 37
• Complexity: 805

Purity/Quality:

≥99% by HPLC ^*data from raw suppliers

S 26948 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=C(C=C1)OCCN2C3=C(C=C(C=C3)C(=O)C4=CC=CC=C4)SC2=O)C(=O)OC
• Description: S26948 is a peroxisome proliferator-activated receptor γ (PPARγ) agonist (EC50 = 8.83 nM in a transactivation assay). It is selective for PPARγ over PPARα, PPARβ/δ, and retinoid X receptor α (RXRα) at 10 μM. S26948 (30 mg/kg per day) decreases serum levels of glucose, triglycerides, non-esterified fatty acids, and insulin and increases hepatic palmitate oxidation in an ob/ob mouse model of type 2 diabetes. It decreases plasma levels of triglycerides and total and non-HDL cholesterol and the surface area of atherosclerotic lesions in the aortic sinus in an E2-KI transgenic mouse model of dyslipidemia and atherosclerosis fed a Western diet when administered at a dose of 30 mg/kg.
• Uses: S26948 is a peroxisome proliferator-activated receptor γ modulator with potent antidiabetes and antiatherogenic effects.

Technology Process of Dimethyl 2-[[4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3-yl)ethoxy]phenyl]methyl]propanedioate

There total 4 articles about Dimethyl 2-[[4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3-yl)ethoxy]phenyl]methyl]propanedioate 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: 85.0%

dimethyl 4-[2-(6-benzoyl-2(3H)-benzothiazolon-3-yl)ethoxy]benzylidenemalonate (353280-40-7) → dimethyl 2-{4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]benzyl}-malonate (353280-43-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; at 20 ℃;

DOI:10.1016/j.bmc.2006.07.029

Reference yield:

4-[2-(6-benzoyl-2(3H)-benzothiazolon-3-yl)ethoxy]benzaldehyde (353283-48-4) → dimethyl 2-{4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]benzyl}-malonate (353280-43-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / piperidine; acetic acid / toluene / Heating

2: 85 percent / hydrogen / Pd/C / dioxane; tetrahydrofuran; methanol / 20 °C

With piperidine; hydrogen; acetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; toluene; 1: Knoevenagel condensation;

DOI:10.1016/j.bmc.2006.07.029

Reference yield:

4-(2-chloroethoxy)benzaldehyde (54373-15-8) → dimethyl 2-{4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]benzyl}-malonate (353280-43-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / potassium carbonate / dimethylformamide / 3 h / Heating

2: 93 percent / piperidine; acetic acid / toluene / Heating

3: 85 percent / hydrogen / Pd/C / dioxane; tetrahydrofuran; methanol / 20 °C

With piperidine; hydrogen; potassium carbonate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene; 2: Knoevenagel condensation;

DOI:10.1016/j.bmc.2006.07.029

upstream raw materials:

dimethyl 4-[2-(6-benzoyl-2(3H)-benzothiazolon-3-yl)ethoxy]benzylidenemalonate

4-[2-(6-benzoyl-2(3H)-benzothiazolon-3-yl)ethoxy]benzaldehyde

4-(2-chloroethoxy)benzaldehyde

6-benzoyl-2(3H)-benzothiazolone

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