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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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Ganesh Pandey et al.
Chemical communications (Cambridge, England), (6)(6), 624-625 (2002-07-18)
A new strategy towards the synthesis of phenanthridone alkaloids has been reported through the synthesis of (+)-2,7-dideoxypancratistatin from D-(-)-quinic acid employing PET initiated carbocyclization of an electron rich aromatics by silylenol ether as a key step.
F Moroni et al.
Cell death and differentiation, 8(9), 921-932 (2001-08-30)
An excessive activation of poly(ADP-ribose) polymerase (PARP) has been proposed to play a key role in post-ischemic neuronal death. We examined the neuroprotective effects of the PARP inhibitors benzamide, 6(5H)-phenanthridinone, and 3,4-dihydro-5-[4-1(1-piperidinyl)buthoxy]-1(2H)-isoquinolinone in three rodent models of cerebral ischemia. Increasing
Miriam León Paumen et al.
Environmental science & technology, 42(9), 3434-3440 (2008-06-05)
This study aimed to monitor PAC availability to the oligochaete Lumbriculus variegatus during 28 days of exposure to spiked sediments, in order to obtain reliable chronic effect concentrations for reproduction. Sediment toxicity tests were performed using three pairs of PAC
Prakash Jagtap et al.
Critical care medicine, 30(5), 1071-1082 (2002-05-15)
To synthesize novel inhibitors of the nuclear enzyme poly(adenosine 5'-diphosphate [ADP]-ribose) synthetase (PARS), also known as poly(ADP-ribose) polymerase (PARP), and to test them in in vitro models of oxidant-induced cytotoxicity and in endotoxin and splanchnic occlusion-reperfusion-induced shock. Randomized, prospective laboratory
Alberto Chiarugi
British journal of pharmacology, 137(6), 761-770 (2002-11-02)
1. In the presence of genotoxic stress poly(ADP-ribose) polymerase-1 (PARP-1) leads to NAD(+) and ATP depletion, participating in the pathogenesis of several disorders including inflammation. Accordingly, chemical inhibitors of PARP-1 are efficacious anti-inflammatories, albeit the underlying molecular mechanisms are still
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