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Novel tryptanthrin derivative, synthetic method and medicinal application thereof

A kind of derivative, tryptamine technology, applied in the field of medicine, can solve problems such as difficult to obtain, difficult to obtain isatoic anhydride derivatives and the like

Active Publication Date: 2016-02-17
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, isatoic anhydride derivatives are not easy to obtain, so tryptanthrin 1-4 derivatives are difficult to obtain

Method used

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  • Novel tryptanthrin derivative, synthetic method and medicinal application thereof
  • Novel tryptanthrin derivative, synthetic method and medicinal application thereof
  • Novel tryptanthrin derivative, synthetic method and medicinal application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0118] Embodiment 1. synthetic tryptanthrin

[0119] Add 0.01 mol of anthranilic acid into a three-necked bottle equipped with a reflux condenser, a magnet, and a thermometer, add 15 mL of toluene, dry SOCl 2 3mL, reflux for 1.0h, stop the reaction, remove the solvent and excess SOCl by rotary evaporation under reduced pressure 2 . Then add 0.01 mol of indoloquinone and 15 mL of dichloromethane to the flask, continue the reflux reaction for 1 h, cool to room temperature, and filter to obtain a yellow solid, which is recrystallized with methanol, dichloromethane or toluene. m.p. 268-269°C (thermometer uncalibrated). Yield 90%. In this way, the following target products were synthesized.

[0120] The obtained compound is used as an active ingredient to form a pharmaceutical composition, or to prepare a pharmaceutical preparation. The compound obtained is characterized as follows:

[0121] Molecular formula: C 15 h 8 N 2 o 2 . Structural characterization of tryptanthri...

Embodiment 2

[0125] Example 2. Synthesis of 8-fluoro-9-chloroindole[2,1-b]quinazoline-6,12-dione / 8-fluoro-7-chloroindole[2,1-b]quinazole Phenyl-6,12-dione

[0126] Add 0.01mol of anthranilic acid into a three-necked flask equipped with a reflux condenser, a magnet, and a thermometer, add 15mL of toluene, dry SOCl 2 3mL, reflux for 1.0h, stop the reaction, and remove the solvent and excess SOCl by rotary evaporation under reduced pressure 2 . Then add 0.01moL of 4-chloro-5-fluoroindolequinone and 15mL of dichloromethane to the flask, continue the reflux reaction for 1.0h, cool to room temperature, filter to obtain a yellow solid, wash with methanol, dichloromethane or Toluene recrystallized. In this way, the following target products were synthesized.

[0127] The obtained compound is used as an active ingredient to form a pharmaceutical composition, or to prepare a pharmaceutical preparation. The compound obtained is characterized as follows:

[0128]

[0129] Fig.28-Fluoro-9-chlo...

Embodiment 3

[0131] Example 3. Synthesis of 7,8-dichloroindole[2,1-b]quinazoline-6,12-dione / 8,9-dichloroindole[2,1-b]quinazoline- 6,12-diketone

[0132] Add 0.01 mol of anthranilic acid into a three-necked bottle equipped with a reflux condenser, a magnet, and a thermometer, add 15 mL of toluene, dry SOCl 2 3mL, reflux for 1.0h, stop the reaction, and remove the solvent and excess SOCl by rotary evaporation under reduced pressure 2 . Add 0.01moL of 4,5-dichloroindolequinone (5,6-dichloroindolequinone) and 15mL of dichloromethane to the flask, continue the reflux reaction for 1.0h, cool to room temperature, and filter to obtain a yellow solid , recrystallized with methanol wash, dichloromethane or toluene. In this way, the following target products were synthesized.

[0133] The obtained compound is used as an active ingredient to form a pharmaceutical composition, or to prepare a pharmaceutical preparation. The compound obtained is characterized as follows:

[0134]

[0135] Fig.3...

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PUM

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Abstract

The invention relates to a novel tryptanthrin (indole[2,1-b] quinazoline-6,12-diketone) derivative, a synthetic method and a medicinal application thereof. A general structural formula is as follows (see the description). The novel tryptanthrin derivative is synthesized through biomimetic synthesis, the general chemical structural formula of the novel derivative is shown in Figure 1, wherein in the formula, R,R1,R2,R3 are halogen, nitro, amido, hydroxy, alkyl, alkoxy and aryl, R1is morpholine, piperidine, N-methylpiperidine, N-ethylpiperidine, isonipecotic acid, piperazine, 1-(2-pyridyl) piperazine, dimethylamine, diethylamine, 1-(2-ethoxy) piperazine and 1-(2-furoyl) piperazine, and an o-aminobenzoic acid derivative reacts with an indole quinone derivative in solvents of methylbenzene, methyl alcohol, ethyl alcohol, dichloromethane, isopropanol and the like, so as to prepare the novel tryptanthrin derivative. The novel tryptanthrin derivative which has a good inhibiting effect and a good antibacterial effect on cancer cells is preliminarily screened through an MTT experiment and an antibacterial experiment, and the medicine has pharmacological effects in the aspects of tumor resistance, antibiosis and inflammation diminishing.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a new tryptanthrin derivative, a synthesis method and a medicinal use thereof. Background technique [0002] Tryptanthrin (Fig.1), belongs to the indole quinazoline alkaloids, the chemical name is indole[2,1-b]quinazoline-6,12-dione (indolo[2,1-b] quinazolin-6,12-dione), is one of the main components of the traditional Chinese medicine Qingdai and Daqingye and its medicinal plants Strobilanthescusia, Polygonum tinctorum Lour and Isatis Einetorial. Tryptanthrin and its derivatives have good antibacterial, anti-inflammatory and anti-cancer effects. [0003] [0004] Fig.1 Structure of tryptanthrin. [0005] There are few natural sources of tryptanthrin and it is mainly obtained synthetically. The synthesis method of tryptanthrin and its derivatives is mainly based on indole quinone and its substituted indole quinone and isatoic anhydride and its substituted isatoic anhydride...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/519A61P35/00A61P29/00A61P31/04
CPCC07D487/04
Inventor 候宝龙王翠玲
Owner NORTHWEST UNIV
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