5,6-dihydrophenanthridin-6-one

• ChemBase ID: 68417
• Molecular Formular: C13H9NO
• Molecular Mass: 195.21666
• Monoisotopic Mass: 195.06841391
• SMILES: c1cccc2[nH]c(=O)c3ccccc3c12
• Canonical SMILES: O=c1[nH]c2ccccc2c2c1cccc2
• InChI: InChI=1S/C13H9NO/c15-13-11-7-2-1-5-9(11)10-6-3-4-8-12(10)14-13/h1-8H,(H,14,15)
• InChIKey: RZFVLEJOHSLEFR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,6-dihydrophenanthridin-6-one
• IUPAC Traditional name: 5H-phenanthridin-6-one
• Synonyms: 6(5H)-Phenanthridinone; 5H-Phenanthridin-6-one; 6-Phenanthridinol; 6-Phenanthridinone; 6-Phenanthridone; PJ 97A; 6(5H)-Phenanthridinone; WD 99-004344; 6-Phenanthridone; phenanthridin-6(5H)-one; 6-(5H)-Phenanthridinone; 6(5H)-Phenanthridinone; NSC 11021; NSC 40943; NSC 61083; 6-(5H)-Phenanthridinone; 6(5H)-5-氮杂菲酮; 6-(5H)-菲啶酮

Database IDs

• CAS Number: 1015-89-0
• EC Number: 213-804-3
• MDL Number: MFCD00004988
• Beilstein Number: 140641
• PubChem SID: 162034148; 24858050
• PubChem CID: 1853

CALCULATED PROPERTIES

• Acid pKa: 13.477064
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.7391102
• LogD (pH = 7.4): 2.7391098
• Log P: 2.7391102
• Molar Refractivity: 60.6697 cm^3
• Polarizability: 23.630543 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 288-294°C; 290 - 292°C; 290-292 °C(lit.)
• Hydrophobicity(logP): 2.196

Safety Information

• Storage Warning: IRRITANT
• RTECS: SG0370000
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... PARP1(142)

Product Information

• Purity: 95%; 95+%; 96%; 98%
• Grade: technical grade
• Empirical Formula (Hill Notation): C13H9NO

DETAILS

Sigma Aldrich - 299634

Packaging
1 g in glass bottle
Application
Reactant involved in:
• Synthesis of 5,6-dihydrophenanthridine sulfonamides1
• Oxidative coupling with diphenylacetylene2
• Direct copper acetate-catalyzed N-cyclopropylation of cyclic amides3Reactant involved in the synthesis and/or pharmacological activity of biologically active molecules including:
• Potassium channel KV1.3 and IK-1 inhibitors4
• HIV-1 integrase inhibitors5

Toronto Research Chemicals - P294900

6-Phenanthridone is a poly(ADP-ribose) polymerase (PARP) inhibitor with immunosuppressive effects. 6-Phenanthridone has been shown to inhibit concanavalin A-induced lymphocyte proliferation.

REFERENCES

• Chiarugi, A. et al.: Br. J. Pharmacol., 137, 761 (2002)
• Nasrabady, S.E. et al.: Cell. Mol. Neurobiol., 31, 503 (2002)
• Weltin, D. et al.: Int. J. Immunopharmacol., 17, 265 (2002)