Phenanthridin-6(5H)-one

Names

[ Name ]:
Phenanthridin-6(5H)-one

[Synonym ]:
phenanthridone
6-phenanthridinol
phenanthridin-6(5H)-one
EINECS 213-804-3
phenanthridin-6-ol
6-(5H)-Phenanthridinone
MFCD00004988
6-Hydroxyphenanthridine
5,6-dihydrophenanthridin-6-one
6(5H)-Phenanthridinone
6(5H)-Phenanthridone
5H-phenanthridin-6-one

Biological Activity

[Description]:

6(5H)-Phenanthridinone is a potent PARP-1 inhibitor and immunomodulator. 6(5H)-Phenanthridinone inhibits cell proliferation and can be used in cancer research[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Epigenetics >> PARP

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Cell Cycle/DNA Damage >> PARP

[References]

[1]. Weltin D, et al. Immunosuppressive activities of 6(5H)-phenanthridinone, a new poly(ADP-ribose)polymerase inhibitor. Int J Immunopharmacol. 1995 Apr;17(4):265-71.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
274.8±7.0 °C at 760 mmHg

[ Melting Point ]:
290-292 °C(lit.)

[ Molecular Formula ]:
C₁₃H₉NO

[ Molecular Weight ]:
195.22

[ Flash Point ]:
158.7±3.1 °C

[ Exact Mass ]:
195.068420

[ PSA ]:
32.86000

[ LogP ]:
2.81

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.642

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SG0370000

CHEMICAL NAME :: 6(5H)-Phenantridinone

CAS REGISTRY NUMBER :: 1015-89-0

LAST UPDATED :: 199410

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C13-H9-N-O

MOLECULAR WEIGHT :: 195.23

WISWESSER LINE NOTATION :: T B666 HMVJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 10 ug/plate

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: LMF-84

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
SG0370000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Molecular design, synthesis and docking study of benz[b]oxepines and 12-oxobenzo[c]phenanthridinones as topoisomerase 1 inhibitors.

Bioorg. Med. Chem. Lett. 19 , 2444-7, (2009)

Benz[b]oxepines 4a-g and 12-oxobenzo[c]phenanthridines 5a-d were designed and synthesized as constrained forms of 3-arylisoquinolines through an intramolecular radical cyclization reaction. Radical cy...

Novel isoquinolinone-derived inhibitors of poly(ADP-ribose) polymerase-1: pharmacological characterization and neuroprotective effects in an in vitro model of cerebral ischemia.

J. Pharmacol. Exp. Ther. 305(3) , 943-9, (2003)

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 A...

Total synthesis of 7-deoxypancratistatin-1-carboxaldehyde and carboxylic acid via solvent-free intramolecular aziridine opening: phenanthrene to phenanthridone cyclization strategy.

Org. Lett. 10(3) , 361-4, (2008)

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 derivat...