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5,6-dihydrobenzo[f]indole[2,3-b]quinoline type compound and synthesis method thereof

A synthesis method and technology of dihydrobenzene, applied in the direction of organic chemistry, etc., can solve the problems of insufficient diversity of biological activity, difficulty in obtaining raw materials, high reaction temperature, etc., achieve excellent thermal stability, improve physiological activity, and expand the effect of application range

Active Publication Date: 2018-06-08
SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] For the above-mentioned deficiencies existing in the prior art, the object of the present invention is to provide a kind of 5,6-dihydrobenzo[f]indolo[2,3-b]quinoline compound, solve the existing α-carboline The problem of insufficient diversity in the skeleton structure and biological activity of its derivatives; also provide the synthesis method of the above-mentioned compound, solve the problem that the raw material of the existing synthesis method is difficult to obtain, use expensive metal catalysts, the reaction temperature is high, the scope of application of the substrate is narrow, and the conditions Issues such as harshness and low yield

Method used

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  • 5,6-dihydrobenzo[f]indole[2,3-b]quinoline type compound and synthesis method thereof
  • 5,6-dihydrobenzo[f]indole[2,3-b]quinoline type compound and synthesis method thereof
  • 5,6-dihydrobenzo[f]indole[2,3-b]quinoline type compound and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Example 1 The synthetic method of 5,6-dihydrobenzo[f]indolo[2,3-b]quinoline

[0026] Add 1.45g (5mmol) 1-((3-indolyl)methylene)-2-tetralone and 50mL dichloromethane into the dry reaction flask, stir well to dissolve, and then continue to 1.07 g (6 mmol) of NBS (N-bromosuccinimide) and 1.34 g (12 mmol) of DABCO (triethylenediamine) were added to the above reaction solution, and the reaction was fully stirred. It is detected that the reactants are completely converted into products by thin-layer chromatography (the silica gel is: GF254, the developing agent is petroleum ether: ethyl acetate (v / v) = 3: 1, and the developed thin-layer plate is dried. , under ultraviolet light or iodine for color judgment). After the reaction was completed, dichloromethane was removed by rotary evaporation under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate (v / v) = 3:1) to...

Embodiment 2

[0034] Example 2 The synthetic method of 12-chloro-5,6-dihydrobenzo[f]indolo[2,3-b]quinoline

[0035] Add 1.62g (5mmol) 1-((4-chloro-3-indolyl) methylene)-2-tetralone and 50mL 1,2-dichloroethane in the dry reaction flask, room temperature ( 20-25°C) under full stirring, continue to add 1.07g (6mmol) NBS (N-bromosuccinimide) and 1.47g (12mmol) DMAP (4-dimethylaminopyridine) successively to the above reaction solution, fully Stir the reaction. It is detected by thin-layer chromatography that the reactants are completely converted into products, which means that the reaction is complete (silica gel is: GF254, the developing agent is petroleum ether: ethyl acetate (v / v)=5:2, and the thin-layer plate after development is dried. , under ultraviolet light or iodine for color judgment). After the reaction was completed, 1,2-dichloroethane was removed by rotary evaporation under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel co...

Embodiment 3

[0043] Example 3 The synthetic method of 5,6-dihydrobenzo[f]indolo[2,3-b]quinoline-11-carboxylic acid methyl ester

[0044] Add 1.74g (5mmol) 1-((5-methoxycarbonyl-3-indolyl) methylene)-2-tetralone and 50mL acetonitrile in the dry reaction flask, fully stir to dissolve, and then At ℃, continue to add 1.78g (10mmol) NBS and 2.07g (15mmol) potassium carbonate successively to the above reaction solution, and fully stir the reaction. It is detected by thin-layer chromatography that the reactants are completely converted into products, which means that the reaction is complete (silica gel: GF254, the developer is petroleum ether: ethyl acetate (v / v) = 2: 1, and the developed thin-layer plate is dried. , under ultraviolet light or iodine for color judgment). After the reaction was completed, acetonitrile was removed by rotary evaporation under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel column chromatography (eluent: petro...

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Abstract

The invention discloses a 5,6-dihydrobenzo[f]indole[2,3-b]quinoline type compound and a synthesis method thereof. 1-((3-indolyl)methylene)-2-tetranap ketoxime is used as a raw material; the 1-((3-indolyl)methylene)-2-tetranap ketoxime is subjected to electrophilic activation through NBS; the intramolecular bromination / cyclization process is realized; then, under the alkali effect, single molecularhydrogen bromide is removed; further, single molecular water is removed through the aromatization process to generate the 5,6-dihydrobenzo[f]indole[2,3-b]quinoline type compound; the beta-tetranap ketoxime intramolecular cyclization / aromatization is realized in the mild system. The method has the advantages that the conditions are mild; the green effect is achieved; a metal catalytic system is not needed; the operation is simple; the cost is low; the safety coefficient is high; the reaction yield is high; the technological process is short; the product separation is simple; the method is applicable to industrial production.

Description

technical field [0001] The invention belongs to the fields of synthetic medicine, chemical industry and application of organic photoelectric materials, and specifically relates to a 5,6-dihydrobenzo[f]indolo[2,3-b]quinoline compound and a synthesis method thereof. Background technique [0002] α-carboline and its derivatives, as an important heterocyclic skeleton, widely exist in some natural products. For example, natural products such as grossularine-1, grossularine-2, and neocryptolepine all contain α-carboline structural units. Due to the planar structure characteristics and the functional groups in the molecule, this kind of compound can be used as a DNA intercalator to inhibit the replication and transcription of DNA, and has important application value in the fields of biology and medicine. Therefore, α-carboline and its derivatives exhibit various biological activities such as anti-inflammatory, anxiolytic, and kinase inhibition. In addition, α-carboline derivative...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 蒋燕袁伟成张晓梅刘应乐杨义鲁越
Owner SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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