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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:
Molecular Weight:
195.22
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

Quality Level

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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E Perkins et al.
Cancer research, 61(10), 4175-4183 (2001-05-19)
Multicellular organisms must have means of preserving their genomic integrity or face catastrophic consequences such as uncontrolled cell proliferation or massive cell death. One response is a modification of nuclear proteins by the addition and removal of polymers of ADP-ribose
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.
Denise Campisi Hegan et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(5), 2201-2206 (2010-02-06)
Inhibitors of poly(ADP-ribose) polymerase (PARP) are in clinical trials for cancer therapy, on the basis of the role of PARP in recruitment of base excision repair (BER) factors to sites of DNA damage. Here we show that PARP inhibition to
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)
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

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