(10S)-10-amino-8-azatricyclo[9.4.0.02,7]pentadeca-1(11),2(7),3,5,12,14-hexaen-9-one

• ChemBase ID: 159993
• Molecular Formular: C14H12N2O
• Molecular Mass: 224.25788
• Monoisotopic Mass: 224.09496301
• SMILES: c12c3c([C@@H](C(=O)Nc1cccc2)N)cccc3
• Canonical SMILES: N[C@@H]1C(=O)Nc2c(c3c1cccc3)cccc2
• InChI: InChI=1S/C14H12N2O/c15-13-11-7-2-1-5-9(11)10-6-3-4-8-12(10)16-14(13)17/h1-8,13H,15H2,(H,16,17)/t13-/m0/s1
• InChIKey: NIDGAHURPWFSKR-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S)-10-amino-8-azatricyclo[9.4.0.0^2,^7]pentadeca-1(11),2(7),3,5,12,14-hexaen-9-one
• IUPAC Traditional name: (10S)-10-amino-8-azatricyclo[9.4.0.0^2,^7]pentadeca-1(11),2(7),3,5,12,14-hexaen-9-one
• Synonyms: (7S)-7-Amino-5,7-dihydro-6H-dibenz[b,d]azepin-6-one; (S)-7-Amino-5H,7H-dibenzo[b,d]azepin-6-one

Database IDs

• CAS Number: 847926-88-9
• PubChem SID: 162254128
• PubChem CID: 25067537

CALCULATED PROPERTIES

• Acid pKa: 12.6074915
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.38408706
• LogD (pH = 7.4): 1.3063357
• Log P: 1.8972353
• Molar Refractivity: 67.7168 cm^3
• Polarizability: 27.008585 Å^3
• Polar Surface Area: 55.12 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A604380

A building block for γ-secretase inhibitors for treatment of Alzheimer's disease. Several γ-secretase inhibitors have been described that contain this compound.

REFERENCES

• Beher, D., et al.: Exp. Opin. Investig. Drugs, 14, 1385 (2005)
• Fauq, A., et al.: Bioorg. Med. Chem. Lett., 17, 6392 (2005)