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299634

Sigma-Aldrich

6-(5H)-Phenanthridinone

technical grade

Synonym(s):

NSC 11021, NSC 40943, NSC 61083

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About This Item

Empirical Formula (Hill Notation):
C13H9NO
CAS Number:
1015-89-0
Molecular Weight:
195.22
EC Number:
213-804-3
MDL number:
MFCD00004988
UNSPSC Code:
12352100
PubChem Substance ID:
24858050
NACRES:
NA.22

grade

technical grade

form

powder

mp

290-292 °C (lit.)

SMILES string

O=C1Nc2ccccc2-c3ccccc13

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)

InChI key

RZFVLEJOHSLEFR-UHFFFAOYSA-N

Gene Information

human ... PARP1(142)

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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.

Application

Reactant involved in:
  • Synthesis of 5,6-dihydrophenanthridine sulfonamides
  • Oxidative coupling with diphenylacetylene
  • Direct copper acetate-catalyzed N-cyclopropylation of cyclic amides

Reactant involved in the synthesis and/or pharmacological activity of biologically active molecules including:
  • Potassium channel KV1.3 and IK-1 inhibitors
  • HIV-1 integrase inhibitors

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Alberto Chiarugi et al.
The Journal of pharmacology and experimental therapeutics, 305(3), 943-949 (2003-02-28)
Excessive activation of poly(ADP-ribose) polymerase-1 (PARP-1), a nuclear enzyme catalyzing the transfer of ADP-ribose units from NAD to acceptor proteins, induces cellular energy failure by NAD and ATP depletion and has been proposed to play a causative role in a
One-pot formation of C-C and C-N bonds through palladium-catalyzed dual C-H activation: synthesis of phenanthridinones.
Guan-Wu Wang et al.
Angewandte Chemie (International ed. in English), 50(6), 1380-1383 (2011-02-04)
J S Ungerstedt et al.
Clinical and experimental immunology, 131(1), 48-52 (2003-01-10)
The present study investigates the modulating effects of nicotinamide on the cytokine response to endotoxin. In an in vitro model of endotoxaemia, human whole blood was stimulated for two hours with endotoxin at 1 ng/ml, achieving high levels of the
Wan-Ju Kim et al.
Toxicology and applied pharmacology, 202(1), 84-98 (2004-12-14)
One of the cellular responses to DNA damaging events is the activation of programmed cell death, also known as apoptosis. Apoptosis is an important process in limiting tumorigenesis by eliminating cells with damaged DNA. This view is reinforced by the
Jonathan Collins et al.
Organic letters, 10(3), 361-364 (2008-01-01)
Solid-state silica-gel-catalyzed opening of aziridine 6 provided phenanthrene 7, whose oxidative cleavage, recyclization, and further elaboration furnished the C-1 aldehyde and carboxylic acid derivatives of 7-deoxypancratistatin for potential analogue synthesis.
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