3-{5-[4-(2-hydroxy-2-methylpropanoyl)piperazin-1-yl]-2-(trifluoromethyl)phenyl}-4-(1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione

• ChemBase ID: 178103
• Molecular Formular: C27H25F3N4O4
• Molecular Mass: 526.5070096
• Monoisotopic Mass: 526.18278996
• SMILES: c1ccc2c(c1)[nH]cc2C1=C(C(=O)NC1=O)c1c(ccc(c1)N1CCN(CC1)C(=O)C(O)(C)C)C(F)(F)F
• Canonical SMILES: O=C(C(O)(C)C)N1CCN(CC1)c1ccc(c(c1)C1=C(C(=O)NC1=O)c1c[nH]c2c1cccc2)C(F)(F)F
• InChI: InChI=1S/C27H25F3N4O4/c1-26(2,38)25(37)34-11-9-33(10-12-34)15-7-8-19(27(28,29)30)17(13-15)21-22(24(36)32-23(21)35)18-14-31-20-6-4-3-5-16(18)20/h3-8,13-14,31,38H,9-12H2,1-2H3,(H,32,35,36)
• InChIKey: CLGRAWDGLMENOD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{5-[4-(2-hydroxy-2-methylpropanoyl)piperazin-1-yl]-2-(trifluoromethyl)phenyl}-4-(1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: 3-{5-[4-(2-hydroxy-2-methylpropanoyl)piperazin-1-yl]-2-(trifluoromethyl)phenyl}-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione
• Synonyms: 3-[5-[4-(2-Hydroxy-2-methyl-1-oxopropyl)-1-piperazinyl]-2-(trifluoromethyl)phenyl]-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione; TCS 21311; TCS-21311

Database IDs

• CAS Number: 1260181-14-3
• PubChem SID: 164234013
• PubChem CID: 50925411

CALCULATED PROPERTIES

• Acid pKa: 8.965879
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.042815
• LogD (pH = 7.4): 3.031711
• Log P: 3.043223
• Molar Refractivity: 134.9751 cm^3
• Polarizability: 50.937084 Å^3
• Polar Surface Area: 105.74 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T012650

A potent JAK3 inhibitor; selective for JAK3 over JAK1, JAK2 and TYK2. It also inhibits GSK-3β, PKCα and PKCθ.

REFERENCES

• Thoma, G. et al.: J. Med. Chem., 54, 284 (2011)