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:

97% ^*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
• General Description: Ellipticine is a 6H-pyrido[4,3-b]carbazole alkaloid known for its notable anticancer properties. A regiospecific total synthesis of ellipticine was achieved through a nitrene insertion strategy, enabling the efficient preparation of ellipticine and its derivatives. This method involved a phenylboronic acid coupling with a bromoisoquinoline intermediate, followed by carbazole ring formation, yielding ellipticine with confirmed structural integrity via spectroscopic and analytical characterization. The synthesis provides a versatile route for producing ellipticine and related alkaloids with potential therapeutic applications.

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:

6-benzyl-5,11-dimethyl-6H-pyrido[4,3-b]carbazole

2-benzoyl-1-cyano-1,2-dihydroellipticine

2-Benzenesulfonyl-5,11-dimethyl-2,6-dihydro-1H-pyrido[4,3-b]carbazole-1-carbonitrile

6-methylellipticine

Refernces

A REGIOSPECIFIC TOTAL SYNTHESIS OF ELLIPTICINE VIA NITRENE INSERTION

10.1016/S0040-4039(00)95184-0

The research focuses on the regiospecific total synthesis of ellipticine, a 6H-pyrido[4,3-b]carbazole alkaloid with significant anticancer activity. The purpose of the study was to develop a general synthetic approach that would allow for the preparation of a number of ellipticine derivatives. The researchers achieved this by employing a versatile coupling reaction between phenylboronic acid and a substituted bromoisoquinoline, followed by carbazole ring formation via a nitrene insertion reaction. This method successfully yielded ellipticine, and the synthesized compound was confirmed through satisfactory spectroscopic (nmr and ir) and analytical (elemental and/or mass spectral) data. The conclusion of the research was the successful completion of a general and regiospecific synthesis route for ellipticine, which could potentially be adapted for the synthesis of other related alkaloids.