6H-indolo[2,3-b]quinoxaline derivative, and preparation method and application thereof

A 3-b, quinoxaline technology, applied in organic chemistry, drug combination, anti-tumor drugs, etc., can solve the problem of anti-tumor activity that has not been reported in the literature, and achieve good anti-tumor activity and good inhibitory activity in vitro

Inactive Publication Date: 2019-12-06
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

6H-indolo[2,3-b]quinoxaline derivatives are an important class of heterocyclic compounds. Currently, there are relatively few reports on their synthesis methods, and the research on their biological activities mainly focuses on antiviral activi

Method used

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  • 6H-indolo[2,3-b]quinoxaline derivative, and preparation method and application thereof
  • 6H-indolo[2,3-b]quinoxaline derivative, and preparation method and application thereof
  • 6H-indolo[2,3-b]quinoxaline derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
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Example Embodiment

[0027] Example 1 Synthesis of compound 3a

[0028] Under electromagnetic stirring, sequentially add o-phenylenediamine (2.16g, 20.0mmol), isatin (2.94g, 20.0mmol) and acetic acid (50mL) into a 250mL round bottom flask; 2 Under protection, place the round-bottomed flask in an electromagnetic stirrer at 120°C and react for 12h (TLC monitors the reaction progress, developing solvent: V DCM :V EA :V MeOH =9:3:1), cool, remove most of the acetic acid under reduced pressure, add water (50mL) dropwise to the reaction mixture, stir, a yellow solid precipitates, filter, and wash the filter cake with water (3×20mL) to obtain Compound 3a 3.94g, bright yellow solid, crude yield 90.0%.

Example Embodiment

[0029] Example 2 Synthesis of Compound 3b

[0030] Replace the isatin in Example 1 with 5-methylisatin, the experimental operation is the same as that in Example 1, to obtain compound 3b The yield was 96.9%, and the melting point was 295-296°C.

Example Embodiment

[0031] Example 3 Synthesis of Compound 3c

[0032] Replace the isatin in Example 1 with 6-methoxyisatin. The experimental operation is the same as that in Example 1, to obtain compound 3c The yield was 96.0%, and the melting point was 295-297°C.

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Abstract

The invention provides a 6H-indolo[2,3-b]quinoxaline derivative, and a preparation method and application thereof. The general formula is as shown in the specification. The preparation method comprises a step of preparing the 6H-indolo[2,3-b]quinoxaline derivative by taking o-phenylenediamine, indoldione, dihaloalkane and amine compounds as raw materials. The compounds provided by the invention show good antitumor activity.

Description

technical field [0001] The present invention relates to the technical fields of organic chemistry and medicinal chemistry, in particular to 6H-indolo[2,3-b]quinoxaline derivatives and their preparation methods and applications. These compounds exhibit good antitumor activity in vitro . Background technique [0002] Malignant tumors are a serious threat to human health and are the second leading cause of death in the world. At present, the incidence of tumors in my country is increasing year by year, seriously endangering human health and a better life. The discovery of new anti-tumor lead compounds has very important research significance. 6H-indolo[2,3-b]quinoxaline derivatives are an important class of heterocyclic compounds. Currently, there are relatively few reports on their synthesis methods, and the research on their biological activities mainly focuses on antiviral activity. (Bioorganic & Medicinal Chemistry Letters 27(2017) 3915-3919; European Journal of Medicina...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61P35/00
CPCA61P35/00C07D487/04
Inventor 潘成学李晓娟苏桂发王增博李昕蔚
Owner GUANGXI NORMAL UNIV
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