Tryptanthrin derivatives, synthesis method and medicinal use thereof

A kind of derivative, tryptamine technology, applied in the field of synthesis, tryptamine derivatives, can solve the problem of difficult to obtain, isatoic anhydride derivatives difficult to obtain and the like

Active Publication Date: 2018-10-30
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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  • Tryptanthrin derivatives, synthesis method and medicinal use thereof
  • Tryptanthrin derivatives, synthesis method and medicinal use thereof
  • Tryptanthrin derivatives, synthesis method and medicinal use 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 tryptanthr...

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] 8-fluoro-9-chloroin...

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] 7,8-...

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Abstract

New derivatives, synthesis methods and medicinal uses of tryptamine (indole[2,1‑b]quinazoline‑6,12‑dione), with the following general structural formula: Tryptamine was synthesized through a biomimetic synthesis pathway New derivatives, the chemical formula of such new derivatives is shown in Figure 1, where: R, R1, R2, R3 = halogen, nitro, amino, hydroxyl, alkyl, alkoxy, etc.; aromatic Base: R1=morpholine, piperidine, N-methylpiperidine, N-ethylpiperidine, isopipericolic acid, piperazine, 1-(2-pyridyl)piperazine, dimethylamine, diethylamine , 1-(2-hydroxyethyl)piperazine, 1-(2-furanoyl)piperazine, composed of anthranilic acid derivatives and indolequinone derivatives in toluene, methanol, ethanol, dichloromethane, iso It is prepared by reacting in solvents such as propanol. Through MTT experiments and antibacterial experiments, new tryptophan compounds with good inhibitory effects on cancer cells and good antibacterial effects were initially screened. This type of drugs is used in anti-tumor, antibacterial, and anti-inflammatory properties. It has pharmacological effects.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a tryptanthrin derivative, a synthesis method and a medicinal use thereof. Background technique [0002] Tryptanthrin belongs to indole quinazoline alkaloids, chemical name is indole[2,1-b]quinazoline-6,12-dione (indolo[2,1-b]quinazolin-6,12 -dione), which is one of the main components of the traditional Chinese medicine Qingdai and Daqingye and its medicinal plants Strobilanthes cusia, Polygonum tinctorum Lour and Isatis Einetorial. Tryptanthrin and its derivatives have good antibacterial, anti-inflammatory and anti-cancer effects. [0003] [0004] The 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 as raw material...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/519A61P35/00A61P29/00A61P31/04
CPCC07D487/04
Inventor 侯宝龙王翠玲梁海华刘建利
Owner NORTHWEST UNIV
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