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
• General Description: 6(5H)-Phenanthridone is a chemical scaffold utilized in the development of retinoic acid receptor-related orphan receptor gamma (RORγ)-selective inverse agonists, demonstrating potential therapeutic relevance for autoimmune diseases and type 2 diabetes. Derived from structural modifications of a liver X receptor (LXR) ligand, this skeleton served as the foundation for optimizing compounds with enhanced RORγ selectivity and inverse agonistic activity, while avoiding LXR agonism. Its derivatives, such as compound **5b**, exhibit high potency and specificity, highlighting its utility as a pharmacophore for targeting RORγ-related pathways.

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:

phenanthridine

6-chlorophenanthridine

bromo-6 phenanthridine

2-chloro-phenanthridin-6-ol

Refernces

Structure-activity relationship-guided development of retinoic acid receptor-related orphan receptor gamma (RORγ)-selective inverse agonists with a phenanthridin-6(5H)-one skeleton from a liver X receptor ligand

10.1016/j.bmc.2014.03.007

The research focused on the development of selective inverse agonists for the retinoic acid receptor-related orphan receptor gamma (RORc) using a phenanthridin-6(5H)-one skeleton, with the aim of addressing autoimmune diseases and type 2 diabetes. The study identified a novel ROR ligand through screening a liver X receptor (LXR) ligand library, leading to the discovery of compound 1 as a weak inverse agonist. Subsequent structure-activity relationship (SAR) studies resulted in the optimization of several compounds, including the lead compound 2h and the highly potent RORc-selective inverse agonist 5b, which demonstrated significant selectivity and lacked LXR agonistic activity. Key chemicals involved in the synthesis included hexa?uoroacetone, various anilines, and phenanthridin-6(5H)-one derivatives, which were synthesized through multiple steps involving condensation, cyclization, and substitution reactions. The findings suggest that these compounds could serve as valuable tools for further elucidation of RORc functions and potential therapeutic agents for related diseases.

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 1015-89-0 6(5H)-Phenanthridone

Send

Send

Metric Ton KG G Pound L ML

Send

Send