2-{4-[({2-[3-fluoro-4-(trifluoromethyl)phenyl]-4-methyl-1,3-thiazol-5-yl}methyl)sulfanyl]-2-methylphenoxy}acetic acid

• ChemBase ID: 154379
• Molecular Formular: C21H17F4NO3S2
• Molecular Mass: 471.4881928
• Monoisotopic Mass: 471.05859829
• SMILES: Cc1cc(ccc1OCC(=O)O)SCc1c(nc(s1)c1ccc(c(c1)F)C(F)(F)F)C
• Canonical SMILES: OC(=O)COc1ccc(cc1C)SCc1sc(nc1C)c1ccc(c(c1)F)C(F)(F)F
• InChI: InChI=1S/C21H17F4NO3S2/c1-11-7-14(4-6-17(11)29-9-19(27)28)30-10-18-12(2)26-20(31-18)13-3-5-15(16(22)8-13)21(23,24)25/h3-8H,9-10H2,1-2H3,(H,27,28)
• InChIKey: HWVNEWGKWRGSRK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[({2-[3-fluoro-4-(trifluoromethyl)phenyl]-4-methyl-1,3-thiazol-5-yl}methyl)sulfanyl]-2-methylphenoxy}acetic acid
• IUPAC Traditional name: 4-[({2-[3-fluoro-4-(trifluoromethyl)phenyl]-4-methyl-1,3-thiazol-5-yl}methyl)sulfanyl]-2-methylphenoxyacetic acid
• Synonyms: 4-[2-(3-Fluoro-4-trifluoromethyl-phenyl)-4-methyl-thiazol-5-ylmethylsulfanyl]- 2-methyl-phenoxy}-acetic acid; GW0742; GW0742; 4-[[[2-[3-Fluoro-4-(trifluoromethyl)phenyl]-4-methyl-5-thiazolyl]methyl]thio]-2-methylphenoxy] Acetic Acid

Database IDs

• CAS Number: 317318-84-6
• MDL Number: MFCD07369423
• PubChem SID: 162248518; 24895123
• PubChem CID: 9934458

CALCULATED PROPERTIES

• Acid pKa: 3.500832
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.0128303
• LogD (pH = 7.4): 2.642582
• Log P: 5.8470445
• Molar Refractivity: 122.0974 cm^3
• Polarizability: 42.117542 Å^3
• Polar Surface Area: 59.42 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO: >5 mg/mL; Ether; Ethyl Acetate; H2O: insoluble; Methanol
• Apperance: Light Yellow Solid; white solid
• Melting Point: 130-132°C; 134.5-135.5 °C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: PPAR
• Gene Information: human ... PPARA(5465), PPARD(5467), PPARG(5468)

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C21H17F4NO3S2

DETAILS

Sigma Aldrich - G3295

Legal Information
Sold for research purposes under agreement from Glaxo-Smith-Kline
Biochem/physiol Actions
GW0742 is a highly selective PPARδ agonist. EC50 = 1 nM vs 1 and 2 mM for PPARα and PPARγ, respectively.

Toronto Research Chemicals - G930000

A small molecule agonist of the human Peroxisome Proliferator-Activated Recept δ (PPAR δ). It shows an EC50 of 1.1 nM against PPAR δ with 100-fold selectivity over the other human subtypes.

REFERENCES

• Sznaidman, M.L., et al.: Bioorganic and Medicinal Chemistry Letters, 13, 1517 (2003)