Mitoglitazone

Base Information

• Chemical Name: Mitoglitazone
• CAS No.: 146062-49-9
• Molecular Formula: C19H18N2O4S
• Molecular Weight: 370.42200
• UNII: 29I7RP18RG
• DSSTox Substance ID: DTXSID301317736
• Nikkaji Number: J730.386F
• Wikidata: Q27166263
• Metabolomics Workbench ID: 152832
• ChEMBL ID: CHEMBL146624
• Mol file: 146062-49-9.mol

Synonyms:MSDC-0160

Chemical Property of Mitoglitazone

Chemical Property:

• Boiling Point: 623.8±55.0 °C(Predicted)
• PKA: 6.32±0.50(Predicted)
• PSA: 114.15000
• Density: 1.315±0.06 g/cm3(Predicted)
• LogP: 3.07570
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: ≥37 mg/mL in DMSO; insoluble in EtOH; insoluble in H2O
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 370.09872823
• Heavy Atom Count: 26
• Complexity: 534

Purity/Quality:

99% ^*data from raw suppliers

CAY10415 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=CN=C(C=C1)C(=O)COC2=CC=C(C=C2)CC3C(=O)NC(=O)S3
• Recent ClinicalTrials: Study to Evaluate the Safety, Tolerability and Efficacy of Three Dose Levels of Mitoglitazone in Type 2 Diabetic Patients
• Uses: CAY10415 is used to study blood glucose levels and rates of insulin-stimulated lipogenesis.

Technology Process of Mitoglitazone

There total 23 articles about Mitoglitazone 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: 88.0%

5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione (101931-00-4) → rac-5-({p-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione (146062-49-9)

Guidance literature:

With phosphorus pentoxide; dimethyl sulfoxide; triethylamine; In dichloromethane; for 2h;

DOI:10.1021/jm9605694

Reference yield: 70.0%

5-({4-[2-(5-ethyl-2-pyridinyl)-2-(methoxyimino)ethoxy]phenyl}methyl)-2,4-thiazolidinedione (1359827-44-3) → rac-5-({p-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione (146062-49-9)

Guidance literature:

With hydrogenchloride; water; 2-oxo-propionic acid; at 75 ℃; for 2h;

DOI:10.1016/j.tetlet.2019.07.022

Reference yield:

2-bromo-1-(5-ethyl-2-pyridinyl)ethanone O-methyloxime (1359827-43-2) + 5-(4-hydroxybenzyl)-2,4-thiazolidinedione (74772-78-4) → rac-5-({p-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione (146062-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butylate / dimethyl sulfoxide / 0.25 h / 20 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: hydrogenchloride; water; 2-oxo-propionic acid / 2 h / 75 °C

With hydrogenchloride; potassium tert-butylate; water; 2-oxo-propionic acid; In dimethyl sulfoxide;

DOI:10.1016/j.tetlet.2019.07.022

upstream raw materials:

5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione

Pioglitazone

rac-2-(2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxy}ethyl)-5-ethylpyridine-1-oxide

2,5-dibromopyridine