(9E)-9-[2-(4-bromophenyl)hydrazin-1-ylidene]-5H,6H,7H,8H,9H-pyrido[3,2-b]azepin-6-one

• ChemBase ID: 167541
• Molecular Formular: C15H13BrN4O
• Molecular Mass: 345.19392
• Monoisotopic Mass: 344.02727306
• SMILES: N1C(=O)CC/C(=N\Nc2ccc(cc2)Br)/c2c1cccn2
• Canonical SMILES: O=C1CC/C(=N\Nc2ccc(cc2)Br)/c2c(N1)cccn2
• InChI: InChI=1S/C15H13BrN4O/c16-10-3-5-11(6-4-10)19-20-13-7-8-14(21)18-12-2-1-9-17-15(12)13/h1-6,9,19H,7-8H2,(H,18,21)/b20-13+
• InChIKey: AEELCBKXLYOXEY-DEDYPNTBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9E)-9-[2-(4-bromophenyl)hydrazin-1-ylidene]-5H,6H,7H,8H,9H-pyrido[3,2-b]azepin-6-one
• IUPAC Traditional name: (9E)-9-[2-(4-bromophenyl)hydrazin-1-ylidene]-5H,7H,8H-pyrido[3,2-b]azepin-6-one
• Synonyms: 7,8-Dihydro-9-[2-(4-bromophenyl)hydrazone]-5H-pyrido[3,2-b]azepine-6,9-dione

Database IDs

• CAS Number: 676596-64-8
• PubChem SID: 162261674
• PubChem CID: 46781303

CALCULATED PROPERTIES

• Acid pKa: 12.136649
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.8679945
• LogD (pH = 7.4): 2.8685648
• Log P: 2.8686073
• Molar Refractivity: 86.405 cm^3
• Polarizability: 31.501827 Å^3
• Polar Surface Area: 66.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 213-217°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D448600

A GSK-3 inhibitor; use to maintain potency of cultured multipotent non-embryonic progenitor cells. An intermediate of 1-Azakenpaullone and other Kenpaullone derivatives.

REFERENCES

• Kunick, C., et al.: Bioorg. Med. Chem. Lett., 14, 413 (2004)
• Stukenbrock, H., et al.: J. Med. Chem., 51, 2196 (2004)