5-{[4-(pyridin-4-yl)quinolin-6-yl]methylidene}-1,3-thiazolidine-2,4-dione

• ChemBase ID: 169781
• Molecular Formular: C18H11N3O2S
• Molecular Mass: 333.36384
• Monoisotopic Mass: 333.05719761
• SMILES: c1(ccc2c(c1)c(ccn2)c1ccncc1)C=C1C(=O)NC(=O)S1
• Canonical SMILES: O=C1NC(=O)C(=Cc2ccc3c(c2)c(ccn3)c2ccncc2)S1
• InChI: InChI=1S/C18H11N3O2S/c22-17-16(24-18(23)21-17)10-11-1-2-15-14(9-11)13(5-8-20-15)12-3-6-19-7-4-12/h1-10H,(H,21,22,23)
• InChIKey: QDITZBLZQQZVEE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[4-(pyridin-4-yl)quinolin-6-yl]methylidene}-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-{[4-(pyridin-4-yl)quinolin-6-yl]methylidene}-1,3-thiazolidine-2,4-dione
• Synonyms: (5Z)-5-[[4-(4-Pyridinyl)-6-quinolinyl]methylene]-2,4-thiazolidinedione; GSK 1059615

Database IDs

• CAS Number: 958852-01-2
• PubChem SID: 162263913
• PubChem CID: 71317162

CALCULATED PROPERTIES

• Acid pKa: 7.903143
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.331355
• LogD (pH = 7.4): 2.3185601
• Log P: 2.4371665
• Molar Refractivity: 93.1216 cm^3
• Polarizability: 37.883358 Å^3
• Polar Surface Area: 71.95 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G797450

GSK 1059615 is a potent inhibitor of PI 3-kinase α (PI3Kα). GSK 1059615 inhibits proliferation in BT474 cells and attenuates MAPK signaling.

REFERENCES

• Saadia, et al.: Clin. Cancer Res., 15, 3029 (2009)
• Knight, et al.: ACS Med. Chem. Lett., 1, 39 (2009)