6(5H)-Phenanthridone

Synonym(s):NSC 11021;NSC 40943;NSC 61083

CAS NO.：1015-89-0
Empirical Formula: C13H9NO
Molecular Weight: 195.22
MDL number: MFCD00004988
EINECS: 213-804-3
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-21 22:41:43

What is 6(5H)-Phenanthridone?

The Uses of 6(5H)-Phenanthridone

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.

The Uses of 6(5H)-Phenanthridone

6(5H)-Phenanthridinone is used as a probe into the role of PARP in cellular response to irradiation. Treatment of cells with 6(5H)-Phenanthridinone and various DNA-damaging agents showed a resistance to apoptosis. It acts as a reactant in the synthesis of 5,6-dihydrophenanthridine sulfonamides, oxidative coupling with diphenylacetylene, direct copper acetate-catalyzed N-cyclopropylation of cyclic amides. It is used as HIV-1 integrase inhibitor.

What are the applications of Application

6(5H)-Phenanthridinone is an immunosuppressant PARP inhibitor

Definition

ChEBI: A member of the class of phenanthridines that is phenanthridine with an oxo substituent at position 6. A poly(ADP-ribose) polymerase (PARP) inhibitor, it has been shown to exhibit immunosuppressive activity.

Synthesis Reference(s)

Canadian Journal of Chemistry, 35, p. 180, 1957 DOI: 10.1139/v57-027
Journal of the American Chemical Society, 79, p. 1245, 1957 DOI: 10.1021/ja01562a054

General Description

6-(5H)-Phenanthridinone is an inhibitor of poly(ADP-ribose)polymerase (PARP)-1 activity. The ability of 6-(5H)-phenanthridinone to potentiate the effect of ionizing radiation on tumour cells was evaluated. Action of 6-(5H)-phenanthridinone, one of the most potent PARP inhibitor, on RDM4 murine lymphoma cells in culture was evaluated.

Properties of 6(5H)-Phenanthridone

Melting point:	290-292 °C(lit.)
Boiling point:	435 °C
Density	1.230±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
solubility	DMF: 1mg/mL; DMF:PBS (pH 7.2) (1:5): 0.16mg/mL
pka	13.27±0.20(Predicted)
form	powder to crystal
color	White to Light yellow to Light orange
Water Solubility	Soluble in DMSO (5 mg/ml). Insoluble in water.
λmax	338nm(EtOH)(lit.)
BRN	140641
CAS DataBase Reference	1015-89-0(CAS DataBase Reference)
NIST Chemistry Reference	6(5H)-phenanthridinone(1015-89-0)
EPA Substance Registry System	6-Phenanthridinone (1015-89-0)

Safety information for 6(5H)-Phenanthridone

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H332:Acute toxicity,inhalation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.