10371-86-5

Basic information

• Product Name: 9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
• Synonyms: 9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole;9-methoxyellipticine;9-Methoxyellipticin;ICIG-772;NSC-69187
• CAS NO: 10371-86-5
• Molecular Formula: C₁₈H₁₆N₂O
• Molecular Weight: 276.33244
• EINECS: 233-812-0
• Mol File: 10371-86-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 286.5°C (rough estimate)
• Boiling Point: 419.24°C (rough estimate)
• Flash Point: 168.4°C
• Appearance: /
• Density: 1.1318 (rough estimate)
• Vapor Pressure: 1.41E-10mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• CAS DataBase Reference: 9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole(10371-86-5)
• EPA Substance Registry System: 9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole(10371-86-5)

Safety Data

• Hazardous Substances Data: 10371-86-5(Hazardous Substances Data)

Usage

Description

An Ochrosia alkaloid present in O. oppositifolia and O. sandwicensis Gray, it occurs mainly in the bark of these species. It forms light yellow crystals and gives an ultraviolet spectrum in EtOH with absorption maxima at 242, 275, 290 and 335 mil. It may be characterized as the hydrochloride which has m.p. 288- 290°C following a change in crystal form at 255-265°C, or as the picrate, m.p. 273-5°C. The structure has been elucidated from the mass spectrum fragmentation pattern.

Synthesis Reference(s)

The Journal of Organic Chemistry, 72, p. 7106, 2007 DOI: 10.1021/jo070774z

References

Buzas, Osowiecki, Schindler., Cornpt. Rend., 247, 1390 (1958) Goodwin, Smith, Horning.,!. Arner. Chern. Soc., 81,1903 (1959) Mass spectrum: Loder., Austral. J. Chern., 19, 1947 (1966) Synthesis: Dalton et aI., Austral. J. Chern., 20, 2715 (1967)

InChI:InChI=1/C18H16N2O.ClH/c1-10-15-9-19-7-6-13(15)11(2)18-17(10)14-8-12(21-3)4-5-16(14)20-18;/h4-9,20H,1-3H3;1H

Upstream product

• 917-54-4 methyllithium 
• 81589-46-0 1-acetyl-3-<1-<3-(4-cyanopyridyl)>ethyl>-5-methoxyindole 
• 84537-57-5 5-Methoxy-1-(5,8-Dimethylisoquinolin-6-yl)-1H-benzotriazole 
• 156055-61-7 ethyl 9-methoxy-5,11-dimethyl-6H-pyrido<4,3-b>carbazole-1-carboxylate 
• 952303-63-8 C₁₈H₁₆N₄O 
• 103771-52-4 2,2-diethoxy-N-((6-methoxy-1,4-dimethyl-9H-carbazol-3-yl)methyl)ethanamine 
• 952303-56-9 2-(4-bromo-2,5-dimethylbenzyl)malonic acid diethyl ester 
• 900027-21-6 3-(4-bromo-2,5-dimethylphenyl)propionic acid 
• 952303-57-0 6-bromo-4,7-dimethylindan-1-one 
• 952303-61-6 6-bromo-4,7-dimethylindan-1-ol 
• 952303-58-1 5-bromo-4,7-dimethyl-1H-indene 
• 952303-59-2 7-bromo-5,8-dimethylisoquinoline 
• 1074-24-4 2,5-dibromo-p-xylene 
• 88111-74-4 bromo-4 dimethyl-2,5 benzaldehyde 

Downstream Products

• 78287-42-0 2-(2-chloromethylbenzoyl)-1-cyano-9-methoxy-1,2-dihydroellipticine 
• 74606-38-5 2-benzoyl-1-cyano-9-methoxy-1,2-dihydroellipticine 
• 67-56-1 methanol 
• 76004-29-0 9-oxoellipticine 
• 51131-85-2 9-hydroxyellipticine 
• 18073-32-0 9-Methoxy-5,6,11-trimethyl-6H-pyrido<4,3-b>carbazol 
• 56501-52-1 6-methyl-9-hydroxyellipticine 
• 78287-44-2 C₂₆H₂₀N₂O₂ 
• 124040-08-0 Acetate₉-methoxy-5,11-dimethyl-2-(4-{3-[4-((5Z,10Z,14Z,19Z)-10,15,20-tri-p-tolyl-porphyrin-5-yl)-phenoxy]-propylcarbamoyl}-butyl)-6H-pyrido[4,3-b]carbazol-2-ium; 
• 124040-06-8 N²-valeric acid-9-methoxyellipticinium chloride 

Relevant articles and documents

Ellipticines and 9-acridinylamines as inhibitors of d-alanine:d-alanine ligase

d-Alanine:d-alanine ligase (Ddl), an intracellular bacterial enzyme essential for cell wall biosynthesis, is an attractive target for development of novel antimicrobial drugs. This study focused on an extensive evaluation of two families of Ddl inhibitors encountered in our previous research. New members of both families were obtained through similarity search and synthesis. Ellipticines and 9-acridinylamines were both found to possess inhibitory activity against Ddl from Escherichia coli and antimicrobial activity against E. coli and Staphylococcus aureus. Ellipticines with a quaternary methylpyridinium moiety were the most potent among all studied compounds, with MIC values as low as 2 mg/L in strains with intact efflux mechanisms. Antimicrobial activity of the studied compounds was connected to membrane damage, making their development as antibacterial drug candidates unlikely unless analogues devoid of this nonspecific effect can be discovered.

Simple method for preparing ellipticine or substituted ellipticine

The invention relates to a synthesis process for preparing ellipticine. Ellipticine is obtained through six steps of reaction and three steps of crystallization separation, the target product total yield is high, column chromatography separation is not needed for an intermediate product and the target product, and the method is particularly suitable for large-scale preparation.

Friedel-crafts cyclodehydration approach toward the synthesis of ellipti-cine and 9-methoxyellipticine

An expedient synthesis of biologically important pyrido[4,3-b]carbazole alkaloids, ellipticine and 9-methoxyellipticine, is reported. Our synthetic approach applies a key H3PO4-mediated Friedel-Crafts cyclodehydration to construct the pyridine core.