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

• 5784-95-2 2-(4-methoxyphenyl)-1H-indole 
• 95-20-5 2-methyl-1H-indole 
• 5670-66-6 1-nitro-2-(2-nitrovinyl)benzene 
• 450380-19-5 11-trimethylsilylneocryptolepine 
• 197524-37-1 1-methyl-3-(o-aminophenyl)-1H-quinoline-2-one 
• 243-38-9 6H-quinindoline 
• 77-78-1 dimethyl sulfate 
• 1093116-12-1 2-((1H-indol-3-yl)methyl)aniline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 586-96-9 Nitrosobenzene 
• 91-22-5 quinoline 
• 3947-76-0 N-methylquinolinium iodide 
• 140-29-4 phenylacetonitrile 
• 16714-25-3 2-azidobenzaldehyde 

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.

Synthetic studies towards benzofuro[2,3-b]quinoline and 6H-indolo[2,3-b]quinoline cores: Total synthesis of norneocryptolepine and neocryptolepine

An innovative acid-assisted cascade transformation of indoles with 2-nitrostyrenes was developed, allowing for the one-pot assembly of heterocyclic scaffolds with four fused rings. This strategy was subsequently employed for the concise total synthesis of two natural products, the alkaloids norneocryptolepine and neocryptolepine.

Design, Synthesis, and Antifungal Evaluation of Neocryptolepine Derivatives against Phytopathogenic Fungi

Neocryptolepine is an alkaloid isolated from traditional African herbal medicine Cryptolepis sanguinolenta, and its broad spectrum of biological activities has been illuminated in past decades. In this study, neocryptolepine and its derivatives (1-49) were designed and synthesized from economical and readily available starting materials. Their structures were confirmed by proton nuclear magnetic resonance, carbon nuclear magnetic resonance, and mass spectrometry. The synthesized compounds were screened for their antifungal profile against six agriculturally important fungi Rhizoctonia solani, Botrytis cinerea (B. cinerea), Fusarium graminearum, Mycosphaerella melonis, Sclerotinia sclerotiorum, and Magnaporthe oryzae. The results of in vitro assay revealed that compounds 5, 21, 24, 35, 40, 45, and 47 presented remarkable antifungal activity against the fungi tested with EC50 values lower than 1 μg/mL. Significantly, compound 24 displayed the most effective inhibitory potency against B. cinerea (EC50 = 0.07 μg/mL), and the data from in vivo experiments revealed that compound 24 demonstrated comparable protective activity with the positive control boscalid. Preliminary mechanism studies indicated that compound 24 showed impressive spore germination inhibitory effectiveness and lower cytotoxicity than azoxystrobin, imparted on normal function of the cell membrane and cell wall, and arrested the normal function of the nucleus. Besides the excellent inhibitory activity against agriculturally important phytopathogenic fungi tested, the designed assemblage possesses several benefits with a high profile of variation in synthesized molecules, the ease of synthesis, and good cost-effectiveness of commercially available synthetic reagents, all of these have highlighted the potential worth of compound 24 as a new and highly efficient agricultural fungicide.