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Merck
CN

299634

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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
213-804-3
MDL number:
Form:
powder
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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)

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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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
Sajjad Ahmad et al.
Organic & biomolecular chemistry, 10(19), 3937-3945 (2012-04-06)
A new synthetic approach has been developed for the preparation of 7-deoxypancratistatin analogues bearing a syn-(4aS,10bS)-phenanthridone ring junction. A one-pot tandem process involving a substrate-directed Overman rearrangement and ring closing metathesis reaction was developed for the stereoselective synthesis of a
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



Global Trade Item Number

SKUGTIN
299634-1G04061826238905