Ellipticine

Base Information

• Chemical Name: Ellipticine
• CAS No.: 519-23-3
• Molecular Formula: C17H14 N2
• Molecular Weight: 246.312
• Hs Code.: 2933990090
• European Community (EC) Number: 208-264-0
• NSC Number: 71795
• UNII: 117VLW7484
• DSSTox Substance ID: DTXSID30199855
• Nikkaji Number: J6.591I
• Wikipedia: Ellipticine
• Wikidata: Q10359556
• Pharos Ligand ID: RG3S8K3291TW
• Metabolomics Workbench ID: 122960
• ChEMBL ID: CHEMBL123
• Mol file: 519-23-3.mol

Synonyms:5,11-dimethyl-6H-pyrido(4,3-b)carbazole;ellipticine;ellipticine hydrochloride;ellipticine tartrate;NSC 71795

Chemical Property of Ellipticine

Chemical Property:

• Vapor Pressure: 1.81E-09mmHg at 25°C
• Melting Point: 316-318°C
• Refractive Index: 1.5794 (estimate)
• Boiling Point: 495.4°Cat760mmHg
• PKA: 16.59±0.40(Predicted)
• Flash Point: 227.1°C
• PSA: 28.68000
• Density: 1.257g/cm³
• LogP: 4.48610
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 246.115698455
• Heavy Atom Count: 19
• Complexity: 342

Purity/Quality:

99%, ^*data from raw suppliers

Ellipticine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C2C=CN=CC2=C(C3=C1NC4=CC=CC=C43)C
• Description: Ellipticine is an alkaloid isolated from Apocyanaceae plants that exhibits antitumor activities by intercalating into DNA and/or inhibiting DNA topoisomerase II. It forms covalent adducts in DNA after being enzymatically activated with cytochrome P450 isoforms (e.g., CYP3A4, CYP1A1, or CYP1A2) or by peroxidases in target tissues. Ellipticine has been shown to inhibit the proliferation of human breast adenocarcinoma MCF-7 cells, leukemia HL-60 and CCRF-CEM cells, neuroblastoma IMR-32, UKF-NB-3, and UKF-NB-4 cells, and U87MG glioblastoma cells with IC50 values ranging from 0.27-4.7 μM.

Technology Process of Ellipticine

There total 166 articles about Ellipticine 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%

C27H32N2O4S (954375-96-3) → ellipticine (519-23-3)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 0.333333h; Heating;

DOI:10.1016/j.tetlet.2007.07.160

Reference yield: 96.0%

6-azido-5,8-dimethyl-7-phenylisoquinoline (123190-46-5) → ellipticine (519-23-3)

Guidance literature:

In various solvent(s); at 180 ℃;

DOI:10.1016/S0040-4039(00)95184-0

Reference yield: 92.0%

1-chloro-5,11-dimethyl-6,11-dihydro-5H-pyrido[4,3-b]carbazole → ellipticine (519-23-3)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In acetic acid; under 760.051 Torr;

DOI:10.1002/1099-0690(200112)2001:23<4543::aid-ejoc4543>3.0.co;2-#

upstream raw materials:

1-[1-acetyl-3-(1,1-di-indol-3-yl-ethyl)-1,4-dihydro-[4]pyridyl]-ethanone

2-(p-methoxbenzyl)-1,2,3,4-tetrahydro-5,11-dimethylpyrido<4,3-b>carbazole

methyllithium

5-hydroxy-5-methyl-indolo<1,2-b><2,7>naphthyridin-12-one

Downstream raw materials:

nitro-9 ellipticine

11-<2-(2,3,5-tribenzoyl-β-D-ribofuranos-1-yl)oxyethyl>-5,6-dimethyl-pyrido<4,3-b>-carbazole

2-acetyl-6-methyl-1,2-dihydroellipticin-1-one

6-methyl-1,2-dihydroellipticin-1-one

Refernces

• 1、 Bergman,Carlsson. "-". . p. 4663,4665. Retrieved 1977.
• 2、 Sainsbury, M.,Watkins, D.,Weerasinghe, D. K.. "Chemistry of 6H-Pyridocarbazoles. Part 10 - Carbon-13 Nuclear Magnetic Resonance Spectra of Ellipticines and some Model Compounds". . p. 117 - 119. Retrieved 1982.
• 3、 Sainsbury,Schinazi. "-". . p. 540. Retrieved 1975.
• 4、 -. "Simple method for preparing ellipticine or substituted ellipticine". Paragraph 0039; 0048; 0049. . Retrieved 2020/05/14.