Darglitazone

Base Information

• Chemical Name: Darglitazone
• CAS No.: 141200-24-0
• Molecular Formula: C23H20 N2 O4 S
• Molecular Weight: 420.489
• UNII: AVP9C03Z3K
• DSSTox Substance ID: DTXSID3057644
• Nikkaji Number: J474.844A
• Wikipedia: Darglitazone
• Wikidata: Q5222642
• NCI Thesaurus Code: C75187
• Metabolomics Workbench ID: 144641
• ChEMBL ID: CHEMBL55624
• Mol file: 141200-24-0.mol

Synonyms:5-(4-(3-(5-methyl-2-phenyl-4-oxazolyl)propionyl)benzyl)-2,4-thiazolidinedione;CP 86325;CP-86,325;CP-86325;darglitazone;darglitazone sodium

Chemical Property of Darglitazone

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 118.06000
• Density: 1.306g/cm³
• LogP: 4.63550
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 420.11437830
• Heavy Atom Count: 30
• Complexity: 643

Purity/Quality:

≥95% ^*data from raw suppliers

Darglitazone ^*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)CCC(=O)C3=CC=C(C=C3)CC4C(=O)NC(=O)S4
• Uses: Hypoglycemic (oral). Darglitazone is a TZD (thiazolidinedione) that increases the sensiticirt od clls to insulin, stimulating insulin-induced P13K activity at submicromolar concentrations. It increases insulin effectiveness in diabetes mellitus subjects.

Technology Process of Darglitazone

There total 9 articles about Darglitazone 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: 81.0%

5-<<4-<3-(5-methyl-2-phenyl-4-oxazolyl)propionyl>-phenyl>methylene>thiazolidine-2,4-dione (125531-47-7) → Darglitazone (141200-24-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 24h; under 2585.7 Torr; Ambient temperature;

DOI:10.1021/jm00088a022

Reference yield:

terephthalaldehyde mono(diethylacetal) (81172-89-6) → Darglitazone (141200-24-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / diethyl ether / -75 °C

2: 60 percent / manganese dioxide / toluene / 18 h / Heating

3: 1.) sodium hydride / 1.) ether, RT, 25 min, 2.) ether, ethanol, reflux, 6 h

4: 1.) sodium hydride / 1.) THF, RT, 0.5 h, 2.) THF, reflux, 48 h

5: conc. HCl / acetic acid / 5 h / Heating

6: 71 percent / piperidine / ethanol / 24 h / Heating

7: 81 percent / H₂ / Pd/C / tetrahydrofuran / 24 h / 2585.7 Torr / Ambient temperature

With piperidine; hydrogenchloride; manganese(IV) oxide; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; acetic acid; toluene;

DOI:10.1021/jm00088a022

Reference yield:

4-(diethoxymethyl)acetophenone (125532-06-1) → Darglitazone (141200-24-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) sodium hydride / 1.) ether, RT, 25 min, 2.) ether, ethanol, reflux, 6 h

2: 1.) sodium hydride / 1.) THF, RT, 0.5 h, 2.) THF, reflux, 48 h

3: conc. HCl / acetic acid / 5 h / Heating

4: 71 percent / piperidine / ethanol / 24 h / Heating

5: 81 percent / H₂ / Pd/C / tetrahydrofuran / 24 h / 2585.7 Torr / Ambient temperature

With piperidine; hydrogenchloride; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; acetic acid;

DOI:10.1021/jm00088a022

upstream raw materials:

5-<<4-<3-(5-methyl-2-phenyl-4-oxazolyl)propionyl>-phenyl>methylene>thiazolidine-2,4-dione

terephthalaldehyde mono(diethylacetal)

4-[3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl]benzaldehyde

1-<4-(diethoxymethyl)phenyl>ethanol

Downstream raw materials:

5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl>-benzyl>thiazolidine-2,4-dione

5-<4-<3-(5-methyl-2-phemyl-4-oxazolyl)propyl>benzyl>-thiazolidine-2,4-dione

5-{4-[1-[(Z)-Hydroxyimino]-3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-benzyl}-thiazolidine-2,4-dione

5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)-1-hydroxypropyl>benzyl>thiazolidine-2,4-dione

Refernces

• 1、 -. "Agent for improving ketosis". . . Retrieved 2008/06/13.
• 2、 -. "Use of thiazolidinedione derivatives in the treatment of insulin resistance". . . Retrieved 2008/06/13.