114414-78-7

Basic information

• Product Name: 5-methyl-5H-indolo[2,3-b]quinoline
• Synonyms: 5H-quinindoline, 5-methyl-; Cryptotackieine
• CAS NO: 114414-78-7
• Molecular Formula: C₁₆H₁₂N₂
• Molecular Weight: 232.2799
• Mol File: 114414-78-7.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 393.8°C at 760 mmHg
• Flash Point: 191.9°C
• Density: 1.21g/cm³
• Vapor Pressure: 2.08E-06mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: 5-methyl-5H-indolo[2,3-b]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-5H-indolo[2,3-b]quinoline(114414-78-7)
• EPA Substance Registry System: 5-methyl-5H-indolo[2,3-b]quinoline(114414-78-7)

Safety Data

• Hazardous Substances Data: 114414-78-7(Hazardous Substances Data)

Upstream product

• 243-38-9 6H-quinindoline 
• 77-78-1 dimethyl sulfate 
• 5468-85-9 N-phenylquinolin-2-amine 
• 23308-83-0 (2-nitrobenzyl)triphenylphosphonium bromide 
• 103-82-2 phenylacetic acid 
• 101-97-3 Ethyl 2-phenylethanoate 
• 621-06-7 2,N-diphenylacetamide 
• 2859-30-5 2-chloro-3-phenyl-quinoline 
• 95-20-5 2-methyl-1H-indole 
• 5670-66-6 1-nitro-2-(2-nitrovinyl)benzene 
• 5784-95-2 2-(4-methoxyphenyl)-1H-indole 
• 1093116-12-1 2-((1H-indol-3-yl)methyl)aniline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 586-96-9 Nitrosobenzene 

Relevant articles and documents

An efficient synthesis of indoloquinoline alkaloid - Neocryptolepine (cryptotackieine)

A short and convenient method for the synthesis of neocryptolepine (cryptotackieine) is described using Wittig reaction and one-pot reduction-cyclization-dehydration approach as the key steps.

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Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate

A convenient approach toward the indoloquinolines neocryptolepine and 6-methylquinindoline from a common intermediate, is reported. Both sequences, designed for maximum use of accessible reagents and robust conditions, are straightforward and efficient. They involved the amidation of 2-aminobenzaldehyde (prepared by iron-mediated reduction of 2-nitrobenzaldehyde) with 2-nitrophenylacetic acid, followed by a K2CO3-assisted cyclization to form a 3-(2-nitrophenyl)quinolin-2-one as the common precursor. Me2CO3-mediated N-methylation of the lactam, reduction of the nitro moiety and final cyclization resulted in 55% overall yield of neocryptolepine, whereas cyclocondensation and N-methylation afforded 79% overall yield of 6-methyl quinindoline. Thus, the sequences toward the targets entailed two POCl3-promoted C-N bond forming reactions, two Fe-mediated nitro group reductions and two base-promoted transformations.

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).

Acid mediated coupling of aliphatic amines and nitrosoarenes to indoles

Traditionally, amines react with nitrosoarenes to provide the corresponding imines or azo compounds. Herein, we report an acid mediated annulation reaction of aliphatic amines and nitrosoarenes to provide indole derivatives. The elusive direct annulation of aliphatic amines and nitrosoarenes via simultaneous C-C and C-N bond formation was achieved under metal free conditions. This conceptually novel method for indole synthesis does not require pre-functionalization steps for the new C-C and C-N bond formation. The method has been applied for an elegant synthesis of nor-neocryptolepine and neocryptolepine.