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

• ChemBase ID: 169818
• Molecular Formular: C21H18F3NO3S2
• Molecular Mass: 453.4977296
• Monoisotopic Mass: 453.0680201
• SMILES: c1(ccc(cc1C)SCc1c(nc(s1)c1ccc(cc1)C(F)(F)F)C)OCC(=O)O
• Canonical SMILES: OC(=O)COc1ccc(cc1C)SCc1sc(nc1C)c1ccc(cc1)C(F)(F)F
• InChI: InChI=1S/C21H18F3NO3S2/c1-12-9-16(7-8-17(12)28-10-19(26)27)29-11-18-13(2)25-20(30-18)14-3-5-15(6-4-14)21(22,23)24/h3-9H,10-11H2,1-2H3,(H,26,27)
• InChIKey: YDBLKRPLXZNVNB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-methyl-4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)sulfanyl]phenoxy}acetic acid
• IUPAC Traditional name: 2-methyl-4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)sulfanyl]phenoxyacetic acid
• Synonyms: GW1516; GSK-516; GW-501516; GW501516; 2-[2-Methyl-4-[[[4-methyl-2-[4-(trifluoromethyl)phenyl]-5-thiazolyl]methyl]thio]phenoxy]acetic Acid; Methyl-methyl-trifluoromethylphenyl-thiazolyl-methylsulfanyl-phenoxy-acetic Acid; GW 1516; GW 501516; 2-(2-methyl-4-((4-methyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)methylthio)phenoxy)acetic acid; 2-(4-((2-(4-(Trifluoromethyl)phenyl)-4-methylthiazol-5-yl)methylthio)-2-methylphenoxy)acetic acid

Database IDs

• CAS Number: 317318-70-0
• MDL Number: MFCD09033000
• PubChem SID: 162263950
• PubChem CID: 9803963

CALCULATED PROPERTIES

• Acid pKa: 3.5055158
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.8718119
• LogD (pH = 7.4): 2.500396
• Log P: 5.697541
• Molar Refractivity: 121.881 cm^3
• Polarizability: 42.32812 Å^3
• Polar Surface Area: 59.42 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 134-136°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Target: PPAR

Product Information

• Purity: 95+%; 98%
• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - G931500

An experimental drug meant to control lipids and increase the level of HDL, or good cholesterol, in the bloodstream.A cell-permeable, thiazolyl compound that acts as a potent, high affinity, PPARδ agonist. Exhibits selectivity for PPARδ compared to PPARα

REFERENCES

• Oliver, W.R., et al.: Proc. Natl. Acad. Sci., USA, 98, 5306 (2001)
• Sznaidman, M.L., et al.: Bioorg. Med. Chem. Lett., 13, 1517 (2001)
• Wang, Y.X., et al.: Cell, 113, 159 (2001)