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A kind of method of biomimetic synthesis of indirubin and its derivatives

A technology for biomimetic synthesis and derivatives is applied in the field of synthesis of indirubin and derivatives thereof, and can solve the problems of difficult source of 3-acetoxyindole, complicated process route, and difficulty in obtaining raw materials, and achieves high yield, Simple synthetic route and environmentally friendly effect

Inactive Publication Date: 2016-06-15
NORTHWEST UNIV
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AI Technical Summary

Problems solved by technology

[0007] 2) 3-Acetoxyindole Condensation Method: At present, the widely used method for the synthesis of indirubin is to obtain indole quinone and 3-acetoxyindole condensation under stirring at room temperature with sodium carbonate or sodium bicarbonate to obtain indirubin Yuhong (Scheme 2) (A.Beauchard, H.Laborie, H.Rouillard, O.Lozach, Y.Ferandin, R.L.Guével, C.Guguen-Guillouzo, L.Meijer, T.Besson, V.Thiéry.synthesis and kinase inhibitory activity of novel substituted indigoids [J ]. Bioorganic & Medicinal Chemistry, 2009, 17, 6257-6263.), the reaction conditions of this method are simple, but the source of raw material 3-acetoxyindole is not easy to obtain (indole is hydrolyzed under the action of mercuric acetate and acetic acid after 3-iodination , to get 3-acetoxyindole)
[0009] Although the above-mentioned method for synthesizing indirubin is relatively simple, there are problems such as raw materials are not easy to obtain, the process route is complicated or the reaction yield is low.

Method used

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  • A kind of method of biomimetic synthesis of indirubin and its derivatives
  • A kind of method of biomimetic synthesis of indirubin and its derivatives
  • A kind of method of biomimetic synthesis of indirubin and its derivatives

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Experimental program
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Effect test

Embodiment 1

[0035] Embodiment 1. synthetic indirubin

[0036] Weigh 1.47g of indoloquinone into a 100ml three-neck flask, add 40ml of dichloromethane and 1.62g of potassium borohydride respectively, reaction method: stirring and reflux, reaction time: 3.0h, reaction temperature: 40°C, the reaction ends Finally, the solvent was removed by rotary evaporation, and 0.81 g of crude indirubin solid was obtained after crystallization, with a yield of 61.8%. Recrystallization from ethanol gave purple-red needle-like crystals, mp356.2-357.8°C (the thermometer was not corrected).

[0037] Molecular formula: C 16 h 10 N 2 o 2 . Structural characterization of indirubin:

[0038] 1H NMR (400MHz, DMSO-d6) δ (ppm): 11.04 (s, 1H, NH); 10.91 (s, 1H, NH); 8.77 (d, 1H, CH); 7.66 (d, 1H, CH); 7.59 (t,1H,CH); 7.43(d,1H,CH); 7.26(t,1H,CH); 7.03(t,2H,2CH); 6.91(d,1H,CH).

Embodiment 2

[0039] Embodiment 2. synthetic indirubin

[0040] Weigh 1.47g of indoloquinone into a 100ml three-neck flask, add 40ml of xylene and 1.62g of potassium borohydride respectively, reaction method: stirring and reflux, reaction time: 3.0h, reaction temperature: 140°C, after the reaction , the solvent was removed by rotary evaporation, and 0.67 g of crude indirubin was obtained as a purple solid after crystallization, with a yield of 51.1%.

Embodiment 3

[0041] Embodiment 3. synthetic indirubin

[0042] Weigh 1.47g of indoloquinone into a 100ml three-neck flask, add 40ml of dichloromethane and 1.62g of potassium borohydride respectively, reaction method: stirring and reflux, reaction time: 5.0h, reaction temperature: 40°C, the reaction is over Finally, the solvent was removed by rotary evaporation, and 0.78 g of crude indirubin was obtained as a purple solid after crystallization, with a yield of 59.5%.

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Abstract

A method for biomimetic synthesis of indirubin, including the following steps: adding organic solvent and reducing agent to indolequinone for reaction, reaction temperature: -10.0~150.0°C, reaction time: 0.5~72.0h, stirring, refluxing or solvent-free grinding Indirubin is obtained through post-extraction. The ratio of the reducing agent to indolequinone is (amount of substance) (50:1)? ~(?0.001:1), the ratio of indolequinone to organic solvent is 1:(3~6)? (Amount of substance (mol): Volume (L)); The method for synthesizing indirubin derivatives is the same as the method for synthesizing indirubin. The invention has a simple synthesis route, cheap and easily available raw materials, mild reaction conditions, high yield and simple operation.

Description

technical field [0001] The invention belongs to the technical field of synthesis of indirubin and derivatives thereof, and in particular relates to a method for biomimetic synthesis of indirubin and derivatives thereof. Background technique [0002] Indirubin (Fig.1), also known as cannonballine and Yuhong tablet, belongs to the bisindole compound and is the main active ingredient of the traditional Chinese medicine Qingdai, Radix Isatidis and Folium Folium. [0003] [0004] In the 1970s, Chinese scientific researchers isolated and extracted indirubin from the traditional Chinese medicine compound "Danggui Aloe Pills" for the treatment of chronic myeloid leukemia, and successfully used it in clinical treatment of chronic myeloid leukemia, with an effective cure rate of 72.7%. Because it is difficult to extract and isolate indirubin from traditional Chinese medicines Folium Folium, Indigo Daisy and Radix Isatidis, medicinal indirubin is mainly obtained from synthesis. Th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/36
CPCC07D209/36
Inventor 王翠玲刘建利赵丹青刘竹兰张宁
Owner NORTHWEST UNIV