50892-23-4

Basic information

• Product Name: WY-14643
• Synonyms: NSC 310038;Acetic acid, 2-[[4-chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl]thio]-;WY-14643/WY14643;((4-chloro-6-((2,3-dimethylphenyl)amino)-2-pyrimidinyl)thio)-aceticaci;((4-chloro-6-(2,3-xylidino)-2-pyrimidinyl)thio)-aceticaci;4-chloro-6-(2,3-xylidino)-2-*pyrimidinylthioaceti;pirnixicacid;wyeth14,643
• CAS NO: 50892-23-4
• Molecular Formula: C₁₄H₁₄ClN₃O₂S
• Molecular Weight: 323.8
• Product Categories: Inhibitors;Intracellular receptor;Inhibitor
• Mol File: 50892-23-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 155°C
• Boiling Point: 514.4°Cat760mmHg
• Flash Point: 264.9°C
• Appearance: /
• Density: 1.2984 (rough estimate)
• Vapor Pressure: 2.1E-11mmHg at 25°C
• Refractive Index: 1.5630 (estimate)
• Storage Temp.: Store at RT
• Solubility: Soluble in DMSO (up to 40 mg/ml).
• PKA: 2.99±0.10(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 6 months.
• CAS DataBase Reference: WY-14643(CAS DataBase Reference)
• NIST Chemistry Reference: WY-14643(50892-23-4)
• EPA Substance Registry System: WY-14643(50892-23-4)

Safety Data

• Hazard Codes: T
• Statements: 45-22-36/37/38
• Safety Statements: 53-26-36/37/39-45
• WGK Germany: 3
• RTECS: AG2915000
• Hazardous Substances Data: 50892-23-4(Hazardous Substances Data)

Usage

Description

WY-14643 is a selective peroxisome proliferator-activated receptor alpha (PPARα) agonist with an EC50 value of 0.63, 32, and >100 μM for PPARα, γ, and δ, respectively. It exhibits anti-inflammatory activity, reduces LPS-induced inflammation in alveolar epithelial cells, induces "browning" of white adipocytes in combined treatment with retinoic acid, stimulates ADAM10-mediated proteolysis of amyloid precursor protein in a mouse model, and downregulates NFkB transcriptional activity.

Uses

Used in Pharmaceutical Research:
WY-14643 is used as a highly potent PPARα agonist for various pharmaceutical research applications, including the study of its anti-inflammatory properties and its effects on adipocyte browning and amyloid precursor protein proteolysis.
Used in Transfection and Luciferase Assay:
WY-14643 serves as a positive control in transfection and luciferase assays, helping researchers evaluate the efficiency of gene delivery and expression in various cell types.
Used in Autophagic Flux Analysis:
In the field of cell biology, WY-14643 is used to stimulate bone marrow-derived macrophages (BMDM) for autophagic flux analysis, providing insights into the regulation of autophagy and its role in cellular processes.
Used in Fatty Acid Metabolism-Immune Nexus (FAMIN) Expression Analysis:
WY-14643 is utilized in cell culture to analyze the regulation of FAMIN expression, contributing to the understanding of the interplay between fatty acid metabolism and immune responses.

Biological Activity

Selective PPAR α agonist (EC 50 values are 0.63, 32 and > 100 μ M at PPAR α , PPAR γ and PPAR δ respectively). Negatively inhibits NF- κ B transcriptional activity and decreases the inflammatory response in vitro and in vivo .

Biochem/physiol Actions

Selective PPARα agonist.

Safety Profile

Moderately toxic by ingestion. Suspected carcinogen with experimental carcinogenic and tumorigenic data. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cl-, NOx and SOx

References

1) Forman et al. (1997), Hypolipidemic drugs, polyunsaturated fatty acids and eicosanoids are ligands for peroxisome proliferator-activated receptors alpha and delta; Proc. Natl. Acad. Sci. USA, 94 4312 2) Devchand et al. (1996), The PPARalpha-leukotriene B4 pathway to inflammation control; Nature, 384 39 3) Heckler et al. (2015), PPAR-a activation reduced LPS-induced inflammation in alveolar epithelial cells; Exp. Lung Res., 41 393 4) Wang et al. (2015), WY14643 combined with all-trans retinoic acid acts via p38 MAPK to induce “browning” of white adipocytes in mice; Genet. Mol. Res., 14 6978 5) Corbett et al. (2015), Activation of peroxisome proliferator-activated receptor alpha stimulates ADAM10-mediated proteolysis of APP; Proc. Natl. Acad. Sci. USA, 112 8445 6) Merk et al. (2015), Pirinixic acids: flexible fatty acid mimetics with various biological activities; Future Med. Chem., 7 1597

InChI:InChI=1/C14H14ClN3O2S/c1-8-4-3-5-10(9(8)2)16-12-6-11(15)17-14(18-12)21-7-13(19)20/h3-6H,7H2,1-2H3,(H,19,20)(H,16,17,18)

Upstream product

• 91759-33-0 ethyl <<4-chloro-6-<(2,3-dimethylphenyl)oxy>-2-pyrimidinyl>thio>acetate 
• 50892-49-4 ethyl [(4,6-dihydroxypyrimidin-2-yl)-sulfanyl]acetate 
• 50892-12-1 ethyl <<4,6-dichloro-2-pyrimidinyl>thio>acetate 
• 87-59-2 2,3-Dimethylaniline 

Downstream Products

• 65089-17-0 <<4-chloro-6-<(2,3-dimethylphenyl)amino>-2-pyrimidinyl>thio>-N-(2-hydroxyethyl)acetamide 
• 86627-11-4 <<4-ethoxy-6-<(2,3-dimethylphenyl)amino>-2-pyrimidinyl>thio>acetic acid 
• 86627-49-8 ({4-ethoxy-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl}thio)-N-(2-hydroxyethyl)acetamide 
• 91759-34-1 <<4-chloro-6--2-pyrimidinyl>thio>-N-(2-hydroxyethyl)acetamide 

Relevant articles and documents

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Novel pyrimidine and 1,3,5-triazine hypolipidemic agents

New compounds were synthesized by changing the substituents of a trisubstituted pyrimidine, i.e., [[4-chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl]thio]acetic acid, a potent hypolipidemic agent, impaired, however, by a marked hepatomegaly-inducing effect. The structural variations led to the subsidence (14b, i.e., 4-chloro-2-(dimethylamino)-6-[(2,3-dimethylphenyl)amino]pyrimidine) or to the reduction (18b, [[4-chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl]amino]acetic acid) of said untoward effect but still maintained the hypolipidemic effect that, although markedly decreased, still proves significant for serum cholesterol and triglycerides (18b) or for serum triglycerides only (14b).