2-bromo-5,6-dihydrophenanthridin-6-one

• ChemBase ID: 163005
• Molecular Formular: C13H8BrNO
• Molecular Mass: 274.11272
• Monoisotopic Mass: 272.97892588
• SMILES: c1c(cc2c(c1)[nH]c(=O)c1c2cccc1)Br
• Canonical SMILES: Brc1ccc2c(c1)c1ccccc1c(=O)[nH]2
• InChI: InChI=1S/C13H8BrNO/c14-8-5-6-12-11(7-8)9-3-1-2-4-10(9)13(16)15-12/h1-7H,(H,15,16)
• InChIKey: OJWSCRAZKRSYIB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromo-5,6-dihydrophenanthridin-6-one
• IUPAC Traditional name: 2-bromo-5H-phenanthridin-6-one
• Synonyms: 2-Bromo-6(5H)-phenanthridinone; NSC 112910; SG 00589; 2-Bromophenanthridone

Database IDs

• CAS Number: 27353-48-6
• PubChem SID: 162257140
• PubChem CID: 185610

CALCULATED PROPERTIES

• Acid pKa: 11.0184355
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.5078616
• LogD (pH = 7.4): 3.5077634
• Log P: 3.5078628
• Molar Refractivity: 68.2925 cm^3
• Polarizability: 26.23614 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B686395

2-Bromophenanthridone is a 2-bromo substituted derivative of phenathridinone that exhibits aryl hydrocarbon (Ah) receptor antagonist activity. It is also used in the preparation of potential HIV-1 integrase inhibitors.

REFERENCES

• Santostefano, M. et al.: Organohalo. Comp., 93, 253 (1993)
• Patil, S. et al.: Bioorg. Med. Chem., 15, 1212 (1993)