Pirinixic acid

Base Information

• Chemical Name: Pirinixic acid
• CAS No.: 50892-23-4
• Molecular Formula: C14H14ClN3O2S
• Molecular Weight: 323.803
• Hs Code.: 2933599090
• European Community (EC) Number: 621-657-5
• NSC Number: 310038
• UNII: 86C4MRT55A
• DSSTox Substance ID: DTXSID4020290
• Nikkaji Number: J10.256C
• Wikipedia: Pirinixic_acid
• Wikidata: Q7198008
• NCI Thesaurus Code: C29866
• Pharos Ligand ID: LTX354LSU6LX
• Metabolomics Workbench ID: 54598
• ChEMBL ID: CHEMBL295416
• Mol file: 50892-23-4.mol

Synonyms:(4-chloro-6-(2,3-xylidino)-2-pyrimidinylthio)acetic acid;4-chloro-6-(2,3-dimethylphenyl)amino-2-pyrimidinylthioacetic acid;4-chloro-6-(2,3-xylidinyl)-2-pyrimidinylthioacetic acid;CXPTA;pirinixic acid;WY 14,643;Wy 14643;WY-14,643;Wy-14643;WY14,643;Wyeth 14,643;Wyeth-14643

Chemical Property of Pirinixic acid

Chemical Property:

• Vapor Pressure: 2.1E-11mmHg at 25°C
• Melting Point: 155°C
• Refractive Index: 1.5630 (estimate)
• Boiling Point: 514.4°Cat760mmHg
• PKA: 2.99±0.10(Predicted)
• Flash Point: 264.9°C
• PSA: 100.41000
• Density: 1.42g/cm³
• LogP: 3.74010
• Storage Temp.: Store at RT
• Solubility.: Soluble in DMSO (up to 40 mg/ml).
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 323.0495256
• Heavy Atom Count: 21
• Complexity: 361

Purity/Quality:

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

WY 14643 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 45-22-36/37/38
• Safety Statements: 53-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)NC2=CC(=NC(=N2)SCC(=O)O)Cl)C
• Description: WY-14643 (50892-23-4) is a selective PPARα agonist (EC50=0.63, 32 and >100 μM for PPARα,γ and δ, respectively).1? Displays anti-inflammatory activity2 and reduces LPS-induced inflammation in alveolar epithelial cells3. Induces “browning” of white adipocytes in combined treatment with retinoic acid.4? Stimulates ADAM10-mediated proteolysis of? amyloid precursor protein in a mouse model.5 Down regulates NFkB transcriptional activity. Review.6
• Uses: A highly potent PPARα agonist WY-14643 has been used:as a positive control for transfection and luciferase assayto stimulate bone marrow–derived macrophages (BMDM) for autophagic flux analysisto analyze the regulation of fatty acid metabolism-immune nexus (FAMIN) expression in cell culture

Technology Process of Pirinixic acid

There total 6 articles about Pirinixic acid 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: 80.0%

ethyl <<4-chloro-6-<(2,3-dimethylphenyl)oxy>-2-pyrimidinyl>thio>acetate (91759-33-0) → pirinixic acid (50892-23-4)

Guidance literature:

With sodium hydroxide; In ethanol; for 0.0333333h; Heating;

DOI:10.1021/jm00378a016

Reference yield:

2,3-Dimethylaniline (87-59-2) + ethyl <<4,6-dichloro-2-pyrimidinyl>thio>acetate (50892-12-1) → pirinixic acid (50892-23-4)

Guidance literature:

With sodium hydroxide; sodium carbonate; In ethanol; water;

Reference yield:

ethyl [(4,6-dihydroxypyrimidin-2-yl)-sulfanyl]acetate (50892-49-4) → pirinixic acid (50892-23-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / POCl₃, N,N-diethylaniline / 13 h / 107 °C

2: 51.5 percent / NaOH / ethanol / 4 h / Heating

3: 80 percent / 30percent aq. NaOH / ethanol / 0.03 h / Heating

With sodium hydroxide; N,N-diethylaniline; trichlorophosphate; In ethanol;

DOI:10.1021/jm00378a016

upstream raw materials:

ethyl <<4-chloro-6-<(2,3-dimethylphenyl)oxy>-2-pyrimidinyl>thio>acetate

ethyl [(4,6-dihydroxypyrimidin-2-yl)-sulfanyl]acetate

ethyl <<4,6-dichloro-2-pyrimidinyl>thio>acetate

2,3-Dimethylaniline

Downstream raw materials:

<<4-chloro-6-<(2,3-dimethylphenyl)amino>-2-pyrimidinyl>thio>-N-(2-hydroxyethyl)acetamide

<<4-chloro-6--2-pyrimidinyl>thio>-N-(2-hydroxyethyl)acetamide

({4-ethoxy-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl}thio)-N-(2-hydroxyethyl)acetamide

<<4-ethoxy-6-<(2,3-dimethylphenyl)amino>-2-pyrimidinyl>thio>acetic acid

Refernces

• 1、 -. "Treatment of skin conditions by use of PPAR alpha activators". . . Retrieved 2008/06/13.
• 2、 -. "2-PYRIMIDINYLTHIO)ALKANOIC ACIDS, ESTERS, AMIDES AND HYDRAZIDES". . . Retrieved 2008/06/13.