239-09-8

Basic information

• Product Name: 11H-indolo[3,2-c]quinoline
• Synonyms: 11H-Indolo(3,2-c)quinoline; TCMDC-131258
• CAS NO: 239-09-8
• Molecular Formula: C₁₅H₁₀N₂
• Molecular Weight: 218.2533
• Mol File: 239-09-8.mol

Chemical Properties

• Boiling Point: 472.2°C at 760 mmHg
• Flash Point: 219.7°C
• Density: 1.336g/cm³
• Vapor Pressure: 1.25E-08mmHg at 25°C
• Refractive Index: 1.839
• CAS DataBase Reference: 11H-indolo[3,2-c]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 11H-indolo[3,2-c]quinoline(239-09-8)
• EPA Substance Registry System: 11H-indolo[3,2-c]quinoline(239-09-8)

Safety Data

• Hazardous Substances Data: 239-09-8(Hazardous Substances Data)

Usage

Class

Indole alkaloids

Structure

Complex polycyclic

Biological and pharmacological activities

Studied for potential as an antitumor agent and for its anti-inflammatory properties

Potential drug lead

Investigated for the treatment of various diseases

Research focus

Exploring potential applications and mechanisms of action in various biological processes

Chemical compound

Yes

Number of carbon atoms

15

Number of hydrogen atoms

10

Number of nitrogen atoms

2

Applications

Potential use in the development of new drugs for cancer, inflammation, and other diseases

Ongoing research

Actively being studied to better understand its properties and potential therapeutic uses.

Upstream product

• 412300-21-1 4-(1-benzotriazolyl)quinoline 
• 56-23-5 tetrachloromethane 
• 6417-52-3 5,14b-diaza-benzo[b]benzo[5,6]cyclohepta[1,2,3-lm]fluorene-10,15-dione 
• 4295-36-7 2,3-dihydroquinolin-4(1H)-one 
• 59-88-1 phenylhydrazine hydrochloride 
• 865-33-8 potassium methanolate 
• 112330-79-7 4-azido-3-phenylquinoline 
• 108832-13-9 6-Chlor-11H-indolo<3,2-c>chinolin 
• 197524-30-4 3-(2-azidophenyl)quinoline 
• 22394-31-6 N-(3-indolylmethylene)aniline 
• 569328-31-0 N-(2-chlorophenyl)quinolin-4-amine 
• 611-35-8 4-chloroquinoline 
• 5332-24-1 3-bromoquinoline 
• 17266-98-7 methyl 3-[N-phenyl-N-(p-toluenesulfonyl)amino]propionate 

Downstream Products

• 79979-37-6 5-(2-chloromethylbenzoyl)-6-cyano-5,6-dihydro-11H-indolo<3,2-c>quinoline 

Relevant articles and documents

An efficient new route towards biologically active isocryptolepine and γ-carboline derivatives using an intramolecular thermal electrocyclization strategy

An efficient and short route is established for biologically active 11H-indolo[3,2-c]quinoline 1, naturally occurring antiplasmodial isocryptolepine 2 and 5-methyl-11H-indolo[3,2-c]quinoline-5-inium iodide 3 using intramolecular thermal electrocyclization

Synthesis of Benzofuroquinolines via Phosphine-Free Direct Arylation of 4-Phenoxyquinolines in Air

A palladium-catalysed, phosphine-free, direct arylation of 4-phenoxyquinolines, in air is described. Using an intramolecular approach, the ring-closed products are formed in yields of up to 95 %. This approach allows access to a range of benzofuroquinolines. An array of functional groups on both the quinoline and phenoxy rings are tolerated.

Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents

Novel isocryptolepine analogues have been conveniently synthesized and evaluated for antimalarial and antiproliferative activities. We have found 3-fluoro-8-bromo-isocryptolepine (1n) to have the highest activities against chloroquine-resistant K1, chloro

Synthesis and evaluation of the tetracyclic ring-system of isocryptolepine and regioiso-mers for antimalarial, antiproliferative and antimicrobial activities

A series of novel quinoline-based tetracyclic ring-systems were synthesized and evaluated in vitro for their antiplasmodial, antiproliferative and antimicrobial activities. The novel hydroiodide salts 10 and 21 showed the most promising antiplasmodial inhibition, with compound 10 displaying higher selectivity than the employed standards. The antiproliferative assay revealed novel pyridophenanthridine 4b to be significantly more active against human prostate cancer (IC50 = 24 nM) than Puromycin (IC50 = 270 nM) and Doxorubicin (IC50 = 830 nM), which are used for clinical treatment. Pyridocarbazoles 9 was also moderately effective against all the employed cancer cell lines and moreover showed excellent biofilm inhibition (9a: MBIC = 100 μM; 9b: MBIC = 100 μM).

Access to γ-Carbolines: Synthesis of Isocryptolepine

A new method to synthesize γ-carboline derivatives has been developed starting from 3,5-dibromo-4-pyridinamine by monoarylation using the Suzuki–Miyaura cross-coupling reaction followed by the base-mediated ring closure to pyrrole formation. Synthesis of

Triflic acid-mediated N-heteroannulation of β-anilino-β-(methylthio)acrylonitriles: a facile synthesis of 4-amino-2-(methylthio)quinolines

Various functionalised 4-amino-2-(methylthio)quinolines are synthesised through triflic acid-mediated N-heteroannulation of α-functionalized-β-anilino-β-(methylthio)acrylonitriles for the first time. The N-heteroannulation process is highly chemoselective and has mild reaction conditions. However, this process fails in the absence of the β-methylthio group in the acrylonitriles. In addition, a new double N-heteroannulation process is demonstrated to synthesise indolo[3,2-c]quinolines from non-heterocyclic precursors. Natural product isocryptolepine is synthesised in four steps from an acyclic precursor.

Substrate or Solvent-Controlled PdII-Catalyzed Regioselective Arylation of Quinolin-4(1H)-ones Using Diaryliodonium Salts: Facile Access to Benzoxocine and Aaptamine Analogues

Regioselective C3, C5, and C8 arylation of quinolin-4(1H)-ones have been accomplished either by substrate-control or by tuning the reaction solvent. A variety of aryl(mesityl)iodonium triflates could smoothly deliver arylated products in good to excellent yields. Additionally, it offers great flexibility by arylating medicinally potent quinolone related heterocycles such as acridin-9(10H)-one, and phenanthridin-6(5H)-one under standard reaction conditions. This strategy was further extended with diphenyleneiodonium triflate to access oxacine fused quinolines. The post-modifications of synthesized products enhance the further utility of this protocol in organic synthesis. To the best of our knowledge, this is the first report on C5 arylation of quinolin-4(1H)-ones using iodine(III) reagents.

Synthesis of 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed cyclization of indole-3-carbaldehyde oximes

A new method for synthesizing 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed intramolecular electrophilic amination of 2-arylindole-3-carbaldehyde O-acetyl oximes was developed.

Novel convenient one-pot method for the synthesis of indoloquinolines

A novel one-pot method based on the sequence of the Fisher reaction between nitroacetophenone and phenylhydrazines, the reduction with metallic tin directly in polyphosphoric acid, and acylation has been developed for the synthesis of indoloquinolines. Th

A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities

A second generation polyphosphoric acid-mediated one-pot three-component synthesis of indoloquinoline scaffold is developed. This improved version of the process involves electrophilically activated nitroalkanes for the installation of strategic C-C and C-N bonds and ring C assembly. This modification allows the elimination of unnecessary solvent change operations and all steps are carried out in a true, uninterrupted one-pot manner. A further improvement involves the possibility to install an ortho-amino group in situ. A synthetic application of this method is showcased by the concise synthesis of an isocryptolepine alkaloid and its synthetic analogs with potent anticancer activities.