6(5H)-Phenanthridinone

Base Information

• Chemical Name: 6(5H)-Phenanthridinone
• CAS No.: 1015-89-0
• Molecular Formula: C13H9NO
• Molecular Weight: 195.221
• Hs Code.: 29337900
• European Community (EC) Number: 213-804-3
• NSC Number: 61083,40943,11021
• UNII: AVQ13AUB5J
• DSSTox Substance ID: DTXSID0074423
• Nikkaji Number: J69.574B
• Wikidata: Q27145196
• Pharos Ligand ID: 1ZKYVX2ADJHZ
• ChEMBL ID: CHEMBL45245
• Mol file: 1015-89-0.mol

Synonyms:6(5H)-phenanthridinone;phenanthridone

Chemical Property of 6(5H)-Phenanthridinone

Chemical Property:

• Vapor Pressure: 0.005mmHg at 25°C
• Melting Point: 290-292 °C(lit.)
• Refractive Index: 1.642
• Boiling Point: 274.843 °C at 760 mmHg
• PKA: 13.27±0.20(Predicted)
• Flash Point: 158.663 °C
• PSA: 32.86000
• Density: 1.231 g/cm³
• LogP: 2.68130
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in DMSO (5 mg/ml). Insoluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 195.068413911
• Heavy Atom Count: 15
• Complexity: 263

Purity/Quality:

99% ^*data from raw suppliers

6-Phenanthridone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3NC2=O
• Uses: 6-Phenanthridone is a poly(ADP-ribose) polymerase (PARP) inhibitor with immunosuppressive effects. 6-Phenanthridone has been shown to inhibit concanavalin A-induced lymphocyte proliferation. 6(5H)-Phenanthridinone is used as a probe into the role of PARP in cellular response to irradiation. Treatment of cells with 6(5H)-Phenanthridinone and various DNA-damaging agents showed a resistance to apoptosis. It acts as a reactant in the synthesis of 5,6-dihydrophenanthridine sulfonamides, oxidative coupling with diphenylacetylene, direct copper acetate-catalyzed N-cyclopropylation of cyclic amides. It is used as HIV-1 integrase inhibitor.

Technology Process of 6(5H)-Phenanthridinone

There total 232 articles about 6(5H)-Phenanthridinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

9-fluorenone oxime (2157-52-0) → 6(5H)-phenanthridinone (1015-89-0)

Guidance literature:

With polyphosphoric acid (PPA); at 20 - 150 ℃; for 16h;

Reference yield: 97.0%

N-(pivaloyloxy)-[1,1'-biphenyl]-2-carboxamide → 6(5H)-phenanthridinone (1015-89-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(II) bis(trifluoromethanesulfonate); In isopropyl alcohol; at 20 ℃; for 5h; Inert atmosphere;

Reference yield: 97.0%

carbon monoxide (201230-82-2) + 2'-iodo-[1,1'-biphenyl]-2-amine (54147-90-9) → 6(5H)-phenanthridinone (1015-89-0)

Guidance literature:

With palladium complexed dendrimer; N-ethyl-N,N-diisopropylamine; In toluene; at 80 ℃; for 22h; under 5171.48 Torr;

DOI:10.1021/ja053650h

upstream raw materials:

N-phenyl benzoyl amide

phenanthridine

monoperoxyphthalic acid

6-ethylphenanthridine

Downstream raw materials:

2-nitrophenanthridin-6(5H)-one

Refernces

• 1、 Labriola. "-". . p. 329,331. Retrieved 1940.
• 2、 Hagelin, Helena,Oslob, Johan D.,Akermark, Bjoern. "Oxygen as oxidant in palladium-catalyzed inter- and intramolecular coupling reactions". . p. 2413 - 2416. Retrieved 1999.
• 3、 Mosby. "-". . p. 936. Retrieved 1954.
• 4、 Chen, Wei-Lin,Jhang, Yuan-Ye,Hsieh, Jen-Chieh. "Copper-catalyzed intramolecular C–N coupling reaction of aryl halide with amide". . p. 3517 - 3526. Retrieved 2017.
• 5、 Taylor,Kalenda. "-". . p. 1699. Retrieved 1954.
• 6、 Fujita, Reiko,Yoshisuji, Toshiteru,Wakayanagi, Sota,Wakamatsu, Hideaki,Matsuzaki, Hisao. "Synthesis of 5(6H)-phenanthridones using Diels-Alder reaction of 3-nitro-2(1H)-quinolones acting as dienophiles". . p. 204 - 208. Retrieved 2006.
• 7、 Kanaoka,Itoh. "-". . p. 647. Retrieved 1973.
• 8、 Snyder et al.. "-". . p. 2014. Retrieved 1953.
• 9、 Ding, Xiaojuan,Duan, Jindian,Guo, Kai,Mao, Yiyang,Rong, Binsen,Zhang, Lei,Zhu, Ning. "Synthesis of Phenanthridinones by Palladium-Catalyzed Cyclization of N -Aryl-2-aminopyridines with 2-Iodobenzoic Acids in Water". . p. 280 - 284. Retrieved 2020.
• 10、 Fujita, Reiko,Wakayanagi, Sota,Wakamatsu, Hideaki,Matsuzaki, Hisao. "Novel Diels-Alder reaction of 4-nitro-1(2H)-isoquinolones". . p. 209 - 212. Retrieved 2006.