14-bromo-8,18-diazatetracyclo[9.7.0.02,7.012,17]octadeca-1(11),2,4,6,12,14,16-heptaen-9-one

• ChemBase ID: 153739
• Molecular Formular: C16H11BrN2O
• Molecular Mass: 327.17534
• Monoisotopic Mass: 326.00547498
• SMILES: c1ccc2c(c1)c1c(c3cc(ccc3[nH]1)Br)CC(=O)N2
• Canonical SMILES: O=C1Nc2ccccc2c2c(C1)c1cc(Br)ccc1[nH]2
• InChI: InChI=1S/C16H11BrN2O/c17-9-5-6-14-11(7-9)12-8-15(20)18-13-4-2-1-3-10(13)16(12)19-14/h1-7,19H,8H2,(H,18,20)
• InChIKey: QQUXFYAWXPMDOE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 14-bromo-8,18-diazatetracyclo[9.7.0.0^2,^7.0^1^2,^1^7]octadeca-1(11),2,4,6,12,14,16-heptaen-9-one; 14-bromo-8,18-diazatetracyclo[9.7.0.0^2,^7.0^1^2,^1^7]octadeca-1(11),2(7),3,5,12,14,16-heptaen-9-one
• IUPAC Traditional name: 14-bromo-8,18-diazatetracyclo[9.7.0.0^2,^7.0^1^2,^1^7]octadeca-1(11),2,4,6,12,14,16-heptaen-9-one; 14-bromo-8,18-diazatetracyclo[9.7.0.0^2,^7.0^1^2,^1^7]octadeca-1(11),2(7),3,5,12,14,16-heptaen-9-one
• Synonyms: 9-Bromo-7,12-dihydro-indolo-[3,2-d]-[1]benzazepin-6(5H)-one; NSC 664704; Kenpaullone; 9-Bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one; 9-Bromopaullone; Kenpaullone

Database IDs

• CAS Number: 142273-20-9
• MDL Number: MFCD02683595
• PubChem SID: 162247878; 24278507
• PubChem CID: 3820

CALCULATED PROPERTIES

• Acid pKa: 12.954072
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): 3.5067914
• LogD (pH = 7.4): 3.5067902
• Log P: 3.5067914
• Molar Refractivity: 83.3079 cm^3
• Polarizability: 33.262077 Å^3
• Polar Surface Area: 44.89 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble18 mg/mL, clear, yellow; Ethyl Acetate
• Apperance: Dark Yellow Solid; yellow
• Melting Point: >300°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CDC2(983)mouse ... Gsk3b(56637)rat ... Gsk3b(84027)

Product Information

• Purity: ≥99%
• Empirical Formula (Hill Notation): C16H11BrN2O

DETAILS

Sigma Aldrich - K3888

Biochem/physiol Actions
Kenpaullone is a potent inhibitor of CDK1/cyclin B (IC50 = 400 nM), CDK2/cyclin A (IC50 = 680 nM), CDK2/cyclin E (IC50 = 7.5 uM) and CDK5/p25 (IC50 = 850 nM).
Packaging
Store under argon

Toronto Research Chemicals - K162500

The paullones are a novel class of kinase inhibitors, initially identified as CDK inhibitors. Kenpaullone has been found to be a useful GSK-3β inhibitor (IC50=23nM).

REFERENCES

• Zaharevitz, D.W., et al.: Cancer Res., 59, 2566 (1999)
• Leclerc, S., et al.: J. Biol. Chem., 276, 251 (1999)
• Bain, J., et al.: Biochem. J., in press.