Heterocyclic matrine derivatives and preparation methods and applications thereof

A technology for matrine and derivatives, which is applied in the field of heterocyclic matrine derivatives and their preparation, can solve problems such as structural modification not yet carried out, and achieve the effect of obvious timeliness

Active Publication Date: 2017-10-24
ZHONGKAI UNIV OF AGRI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Matrine is an excellent lead compound for the creation of new environmentally friendly pesticides. However, for agricultural pests, research on structural modification and screening of new active derivatives using matrine as a lead compound has not yet been carried out.

Method used

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  • Heterocyclic matrine derivatives and preparation methods and applications thereof
  • Heterocyclic matrine derivatives and preparation methods and applications thereof
  • Heterocyclic matrine derivatives and preparation methods and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1 Indolylmatrine (Ind-Mat) preparation

[0052] S01. Preparation of crude product

[0053] 100mL three-neck flask, filled with N 2 After 5 minutes, 1.23 g of sophocarpine, 0.585 g of indole, 0.76 g of cesium fluoride and 12 mL of petroleum ether were added. Adjust N 2 Flow rate, start glycerin oil bath heating after 5 minutes, keep constant temperature 80°C, add 0.5mL tetramethoxysilane dropwise; stop heating after 6 hours of reaction. During the reaction process, the amount of solvent should be kept at 4-5mL, and 2-3mL can be added if it is insufficient. After the reaction, cool slightly, add 10mL of dichloromethane, stir and filter, evaporate the filtrate to get the crude product.

[0054] S02. Separation, purification and structural characterization

[0055] The crude product obtained in step S01 was separated and purified by silica gel column chromatography.

[0056] (1) Separation conditions

[0057] Stationary phase: 200-300 mesh silica gel 230mL...

Embodiment 2

[0067] Embodiment 2 cyclohexylaminomatrine (Cyc-Mat) preparation

[0068] S11. Preparation of crude product

[0069] Add 0.62g of sophocarpine, 0.55mL of cyclohexylamine, and 4mL of water into a 50mL single-necked flask, and heat in an oil bath at a constant temperature of 60°C for 6 hours under magnetic stirring. After the reaction, cool slightly, add 10mL of dichloromethane, stir and filter, evaporate the filtrate to get the crude product.

[0070] S12. Separation, purification and structural characterization

[0071] The crude product obtained in step S11 was subjected to silica gel column chromatography.

[0072] (1) Separation conditions

[0073] Stationary phase: 200-300 mesh silica gel 230mL;

[0074] Screen the elution system: TLC method screens the elution solvent system, and finally determines that the column chromatography separation mobile phase is ethyl acetate: ethanol = 1:8.

[0075] Column packing and activation: After the wet column packing is completed, ...

Embodiment 3

[0084] Embodiment 3 Bioactivity analysis of two derivatives of the present invention

[0085] 1. Experiment of the inhibitory activity of two derivatives on tumor Hela229 cells

[0086] (1) Experimental plan:

[0087] Test compound: lead compound matrine (Mat) before modification; synthetic experiment raw material, matrine derivative sophocarpine (Sop); two new matrine derivatives of the present invention indolylmatrine (derivative Substance II Ind-Mat) and cyclohexylaminomatrine (derivative III Cyc-Mat).

[0088] Cell culture: The human cervical cancer cells Hela229 to be tested were routinely cultured in a cell incubator with 5% carbon dioxide, 37°C and appropriate humidity with MEM basal medium plus 10% fetal bovine serum.

[0089] MTT detection of cell viability: select cells in good condition and adjust the cell suspension density to 8×10 4 ~1×10 5 cells / mL, inoculated into 96-well plates with 100 μL per well, and the effect of Mat and other drugs on cell proliferatio...

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Abstract

The invention discloses heterocyclic matrine derivatives and preparation methods and applications thereof. Structural formulas of the heterocyclic matrine derivatives are as shown in a formula (I). Two obtained matrine derivatives have an obvious inhibition effect on tumor cells or insect cells, the technical disadvantages in the field are filled, and the matrine derivatives can be applied to research and development of anti-tumor drugs or insecticides. Therefore, a candidate compound is provided for development of novel anti-tumor matrine derivatives or matrine derivatives with insecticidal activity, and the matrine derivatives are of great significance in overall development of the medical activity and the agricultural activity of matrine. The invention further provides preparation methods of the two derivatives. Indole or cyclohexane heterocyclic ring is introduced to the 13th key of a lead compound matrine, so that the biological activity of the matrine is significantly improved; and the preparation method is mild, simple and feasible. The formula is as shown in the specification.

Description

technical field [0001] The present invention relates to the technical field of compound and its separation and preparation, more specifically, to a heterocyclic matrine derivative and its preparation method and application. Background technique [0002] For a long time, malignant tumors have become one of the main diseases that seriously endanger human life and quality of life, and have become the leading cause of death for human beings. Moreover, with the development of the economy and people's ineffective environmental protection, the fatality rate of malignant tumors is still increasing. The World Health Organization predicts that by 2020, there will be 20 million new cases of malignant tumors, of which 12 million will die, most of which will occur in developing countries. For the treatment of malignant tumors, natural products and their derivatives play an important role. According to reports, from 1981 to 2008, anti-tumor drugs derived from natural products accounted f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/22A61P35/00A01P7/04
Inventor 程杏安刘展眉蒋旭红吴波
Owner ZHONGKAI UNIV OF AGRI & ENG
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