158470-95-2

Basic information

• Product Name: 2,5,9,11-tetramethyl-5H-indolo[2,3-b]quinoline
• Synonyms: 2,5,9,11-Tetramethyl-5H-indolo[2,3-b]quinoline; 5H-quinindoline, 2,5,9,11-tetramethyl-
• CAS NO: 158470-95-2
• Molecular Formula: C₁₉H₁₈N₂
• Molecular Weight: 274.3596
• Mol File: 158470-95-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 436.552°C at 760 mmHg
• Flash Point: 217.819°C
• Density: 1.16g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 2,5,9,11-tetramethyl-5H-indolo[2,3-b]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5,9,11-tetramethyl-5H-indolo[2,3-b]quinoline(158470-95-2)
• EPA Substance Registry System: 2,5,9,11-tetramethyl-5H-indolo[2,3-b]quinoline(158470-95-2)

Safety Data

• Hazardous Substances Data: 158470-95-2(Hazardous Substances Data)

Upstream product

• 89-62-3 4-methyl-2-nitroaniline 
• 158470-92-9 4,6-dimethyl-2-(4-methyl-2-nitroanilino)quinoline 
• 158470-93-0 4,6-dimethyl-2-(5-methyl-1-benzotriazolo)quinoline 
• 1026008-36-5 N¹-(4,6-Dimethyl-quinolin-2-yl)-4-methyl-benzene-1,2-diamine 
• 3913-18-6 2-chloro-4,6-dimethylquinoline 
• 77-78-1 dimethyl sulfate 
• 158470-94-1 3,5,7-Trimethyl-11H-10,11-diaza-benzo[b]fluorene 

Relevant articles and documents

Synthesis and structure-activity relationship of methyl-substituted indolo[2,3-b]quinolines: Novel cytotoxic, DNA topoisomerase II inhibitors

In furtherance of our SAR study on the chemistry and antitumor activity of fused nitrogen heteroaromatic compounds, a series of linear, methyl- substituted derivatives of 5H- and 6H-indolo[2,3-b]quinolines were synthesized according to the modified Graebe-Ullmann reaction. To establish the relationship between the physicochemical and biological activities of indolo[2,3-b]quinolines, their lipophilic properties, cytotoxic and antimicrobial activity, and ability to induce topoisomerase II dependent pSP65 DNA cleavage in vitro were investigated. We found that the antimicrobial and cytotoxic activity of indolo[2,3-b]quinolines was strongly influenced by the position, and the number of methyl substituents and the presence of methyl group at pyridine nitrogen was essential for the cytotoxicity of these compounds. All indolo[2,3-b]quinolines belonging to the 5H series, i.e., bearing a methyl group on the pyridine nitrogen, showed significant activity against procaryotic and eucaryotic organisms. They inhibited the growth of Gram-positive bacteria and pathogenic fungi at MIC range 3 x 10-2 to 2.5 x 10-1 μmol/mL, displayed cytotoxicity against KB cells ID50 in the range 2 x 10-3 to 9 x 10-3 μmol/mL, and stimulated the formation of calf thymus topoisomerase II mediated DNA cleavage at concentration between 0.4 and 10 μM. None of the indolo[2,3-b]quinolines belonging to the 6H series, i.e., lacking a methyl group on the pyridine nitrogen, was active in analogous tests. Of the investigated compounds, the most active was 2,5,9,11-tetramethyl-5H-indolo[2,3-b]quinoline, a compound bearing the highest number of symmetrically distributed methyl groups. The interaction of indolo[2,3-b]quinolines with DNA was studied by measuring the increase of calf thymus DNA denaturating temperature (T(m)). The ΔT(m) values for the 5H series were found to be about 10 times as high as those for the 6H compounds. Indolo[2,3-b]quinolines with the highest number of methyl groups had the greatest contribution to the increase in the T(m) of calf thymus DNA. The values of ΔT(m) reached 19 °C and 1.6 °C for the most substituted compounds of both series.