Hydroxypioglitazone

Base Information

• Chemical Name: Hydroxypioglitazone
• CAS No.: 146062-44-4
• Molecular Formula: C19H20N2O4S
• Molecular Weight: 372.445
• UNII: K824X25AYA
• DSSTox Substance ID: DTXSID30399914
• Nikkaji Number: J601.466F
• Wikidata: Q27156475
• NCI Thesaurus Code: C170108
• Metabolomics Workbench ID: 155234
• ChEMBL ID: CHEMBL1267
• Mol file: 146062-44-4.mol

Synonyms:leriglitazone

Chemical Property of Hydroxypioglitazone

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 1.28E-16mmHg at 25°C
• Melting Point: 157-158 °C
• Refractive Index: 1.628
• Boiling Point: 627.6 °C at 760 mmHg
• Flash Point: 333.4 °C
• PSA: 113.82000
• Density: 1.325 g/cm³
• LogP: 2.97930
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 372.11437830
• Heavy Atom Count: 26
• Complexity: 496

Purity/Quality:

98%,99%, ^*data from raw suppliers

Hydroxy Pioglitazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3)O
• Recent ClinicalTrials: A Clinical Study to Assess the Efficacy and Safety of Leriglitazone in Adult Male Subjects With Cerebral Adrenoleukodystrophy
• Recent EU Clinical Trials: An exploratory, open-label, multicenter study in male pediatric patients with cerebral X-linked Adrenoleukodystrophie (cALD) to assess the effect of MIN-102 treatment on the progression of cerebral lesions.
• Description: Hydroxy pioglitazone is a major metabolite of the peroxisome proliferator-activated receptor γ (PPARγ) agonist pioglitazone (Item Nos. 71745 | 22263 | 10028). It is formed from pioglitazone by the cytochrome P450 (CYP) isoform CYP2C8 with minor contributions from CYP3A4. Hydroxy pioglitazone binds to PPARγ (Ki = 1.2 μM) and activates PPARγ in a time-resolved FRET (TR-FRET) assay (EC50 = 2.1 μM).
• Uses: A metabolite of Pioglitazone (P471000).

Technology Process of Hydroxypioglitazone

There total 15 articles about Hydroxypioglitazone 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: 98.0%

5-(4-(2-(5-(1-(methoxymethoxy)ethyl)pyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione (184766-39-0) → Hydroxypioglitazone (146062-44-4)

Guidance literature:

With hydrogenchloride; In methanol; for 2h; Heating;

DOI:10.1021/jm9605694

Reference yield:

methyl 2-bromo-3-<4-<2-<5-(1-memthoxymethoxyethyl)-2-pyridyl>ethoxy>phenyl>propionate (146062-60-4) → Hydroxypioglitazone (146062-44-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOAc / ethanol / 4 h / Heating

2: 2N HCl / 20 h / Heating

With hydrogenchloride; sodium acetate; In ethanol;

DOI:10.1248/cpb.43.2168

Reference yield:

5-(1-hydroxyethyl)-2-methylpyridine (56019-64-8,100189-16-0,110338-86-8) → Hydroxypioglitazone (146062-44-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) hexane, DMF, 0 deg C, 1.5 h, 2.) hexane, DMF, from -78 deg C to RT

2: 27 percent / H₂O / 5 h / 160 °C

3: 62 percent / diethyl azodicarboxylate, Ph₃P / tetrahydrofuran / 18 h / Ambient temperature

4: 58 percent / piperidine / ethanol / 18 h / Heating

5: 61 percent / NaBH₄, 1.0N aq. NaOH, CoCl₂*6H₂O, 2,2'-dipyridyl / dimethylformamide / 42 h / Ambient temperature

6: 98 percent / 2N aq. HCl / methanol / 2 h / Heating

With piperidine; hydrogenchloride; [2,2]bipyridinyl; sodium hydroxide; sodium tetrahydroborate; sodium hydride; triphenylphosphine; cobalt(II) chloride; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm9605694

upstream raw materials:

2-Imino-5-(4-{2-[5-(1-methoxymethoxy-ethyl)-pyridin-2-yl]-ethoxy}-benzyl)-thiazolidin-4-one

5-(4-(2-(5-(1-(methoxymethoxy)ethyl)pyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione

1-(6-methyl-pyridin-3-yl)-ethanone

5-(1-hydroxyethyl)-2-methylpyridine

Downstream raw materials:

Ketopioglitazone

Refernces

• 1、 -. "2,4-THIAZOLIDINEDIONE DERIVATIVES IN THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS". Page/Page column 23; 26. . Retrieved 2015/11/17.
• 2、 Sohda,Ikeda,Meguro. "Studies on antidiabetic agents. XII. Synthesis and activity of the metabolites of (±)-5-[p-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl]-2,4- thiazolidinedione (pioglitazone)". . p. 2168 - 2172. Retrieved 2007/10/03.