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Usage

Uses

Used in Pharmaceutical Industry:
10H-indolo[3,2-b]quinoline is used as an active pharmaceutical ingredient for its antimicrobial, antitumor, and anti-inflammatory activities, making it a promising candidate for the development of new drugs to treat various diseases.
Used in Cancer Treatment:
10H-indolo[3,2-b]quinoline is used as a photosensitizer in photodynamic therapy for the treatment of cancers, where it can generate reactive oxygen species upon light activation, leading to the destruction of cancer cells.
Used in Bioimaging:
10H-indolo[3,2-b]quinoline is used as a fluorescent dye for bioimaging, owing to its fluorescent properties, which allow for the visualization of cellular structures and processes in biological research.
Used in Organic Synthesis:
10H-indolo[3,2-b]quinoline is used as a building block for the synthesis of other complex organic molecules, contributing to the development of new compounds with potential applications in various fields.

InChI:InChI=1/C15H10N2/c1-3-7-12-10(5-1)9-14-15(17-12)11-6-2-4-8-13(11)16-14/h1-9,16H

Upstream product

• 7647-01-0 hydrogenchloride 
• 3260-61-5 indolin-3-one 
• 529-23-7 o-aminobenzaldehyde 
• 848086-11-3 N-(2-bromophenyl)quinolin-3-amine 
• 107468-25-7 3-azido-2-phenyl-3-quinoline 
• 250593-14-7 2'-(3-bromoquinolin-2-yl)aniline 

Downstream Products

• 109130-61-2 10-benzyl-10H-indolo[3,2-b]quinoline 
• 480-26-2 cryptolepine 

Relevant academic research and scientific papers

A concise Friedl?nder/Buchwald-Hartwig approach to the total synthesis of quindoline, a bioactive natural indoloquinoline alkaloid, and toward the unnatural 10-methylquindoline

A new approach toward the synthesis of quindoline, a recognized indoloquinoline alkaloid, is reported. The sequence comprises the synthesis of 2-(2-nitrophenyl)quinoline through an optimized Friedl?nder condensation of 2-amino benzaldehyde with 2-nitroacetophenone, followed by the selective C-3 bromination of the quinoline moiety to direct the cyclization, reduction of the nitro group and a final Buchwald-Hartwig cyclization. In addition, quindoline was also converted to the unnatural 10-methylquindoline by reaction with dimethyl carbonate under DBU promotion. It was found that the non-directed reductive cyclization of 2-(2-nitrophenyl)quinoline results in indazolo[2,3-a]quinoline, instead of yielding quindoline. DFT calculations were employed to explain this reaction outcome; this finding suggested that the result of a previously reported total synthesis of quindoline should be revised.

3-Pyridylnitrene, 2- and 4-pyrimidinylcarbenes, 3-quinolylnitrenes, and 4-quinazolinylcarbenes. Interconversion, ring expansion to diazacycloheptatetraenes, ring opening to nitrile ylides, and ring contraction to cyanopyrroles and cyanoindoles

Precursors of 3-pyridylnitrene and 2- and 4-pyrimidinylcarbenes all afford mixtures of 2- and 3-cyanopyrroles on flash vacuum thermolysis, but 3-cyanopyrroles are the first-formed products. 3-Quinolylnitrenes and 4-quinazolinylcarbenes similarly afford 3-cyanoindoles. 2-Pyrimidinylcarbenes rearrange to 3-pyridylnitrenes, but 4-pyrimidinylcarbenes and 4-quinazolinylcarbenes do not necessarily rearrange to the corresponding 3-pyridylnitrenes or 3-quinolylnitrenes. The ring contraction reactions are interpreted in terms of ring opening of either the nitrenes or the diazacycloheptatetraenes to nitrile ylides.

Synthesis of the benzo-β-carboline isoneocryptolepine: The missing indoloquinoline isomer in the alkaloid series cryptolepine, neocryptolepine and isocryptolepine

7H-Indolo[2,3-c]quinoline has been synthesized in two steps via a new approach starting from commercially available 3-bromoquinoline and 2-bromoaniline. The new methodology consists of two consecutive palladium-catalyzed reactions: a selective Buchwald/Ha