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Chiral silicon-substituted mesembrine as well as synthesis method and application thereof

A technology of escutelline and a synthesis method, which is applied in the directions of silicon organic compounds, chemical instruments and methods, drug combinations, etc., can solve the problems that a single compound cannot achieve the expected effect and the like

Active Publication Date: 2021-07-06
SICHUAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, at present, in the development and application of mesembrine alkaloid compounds, the mixed extract of mesembryana containing these four compounds is used, and the use of a single compound cannot achieve the desired effect.

Method used

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  • Chiral silicon-substituted mesembrine as well as synthesis method and application thereof
  • Chiral silicon-substituted mesembrine as well as synthesis method and application thereof
  • Chiral silicon-substituted mesembrine as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0126] A kind of synthetic method of chiral silicate mesembrine, is characterized in that, comprises the following steps:

[0127] A. 3,4-dimethoxyphenyl Grignard reagent and tetrahydrofuran solution of dichlorocyclobutane for substitution reaction, then add allylmagnesium bromide for substitution reaction to obtain compound A;

[0128] B. After dissolving S-mandelic acid and alkali and acid-binding agent triethylamine in solvent anhydrous dichloromethane, add tert-butylformyl chloride, S-mandelic acid and tert-butylformyl chloride are esterified to obtain crude product;

[0129] The crude product is condensed with propargyl alcohol under the action of the condensing agent dicyclohexylcarboimide and the catalyst 4-dimethylaminopyridine to obtain compound B;

[0130] C. Compound A and compound B carry out ring expansion reaction under the effect of catalyst divinyl rhodium dichloride dimer and ligand compound L, obtain compound C;

[0131] Wherein, the ligand compound L struct...

Embodiment 2

[0144] This embodiment provides a synthetic method of a class of chiral silamethine to further illustrate the present invention, which specifically includes the following steps:

[0145] A. Preparation of Compound A

[0146]

[0147] Add 7.2g of magnesium powder and two grains of iodine (Chengdu Jinshan Chemical Reagent Co., Ltd., 20180828) into 200mL of anhydrous tetrahydrofuran, mix well; add 3g of 3,4-dimethoxybromobenzene to the mixture, and heat to Iodine fades; then add 18.5g of 3,4-dimethoxybromobenzene, stir and react at room temperature for 30min, and obtain the newly prepared 3,4-dimethoxyphenyl Grignard reagent;

[0148] At 0°C, add the obtained 3,4-dimethoxyphenyl Grignard reagent to a tetrahydrofuran solution containing 14.1 g of dichlorocyclobutylsilyl, react at room temperature for 24 h, and then add 120 mL of Allylmagnesium bromide was reacted at room temperature for 24h; then, it was quenched with 100mL of saturated ammonium chloride solution, diluted with...

Embodiment 3

[0191] Based on Example 2, this example studies the activity of the obtained chiral silicate mesembrine I-a to further illustrate the present invention.

[0192] 1. Animals

[0193] 8-week-old C57BL / 6 male mice (purchased from Chengdu Dashuo Experimental Animal Co., Ltd.) were bred. During the feeding, fluorescent lamps were used to maintain light for 12 hours a day, and the room temperature was kept at 22°C; the mice were given sufficient feed and drinking water (all experimental animals All are implemented in accordance with the provisions on the protection of experimental animals);

[0194] 2. Drugs

[0195] It is prepared from silicene compound Ⅰ-a and sulfobeta cyclodextrin aqueous solution (the mass fraction of sulfobeta cyclodextrin is 20%);

[0196] 3. Establishment of chronic mild stress model in mice

[0197] 8-week-old C57BL / 6 male mice were subjected to continuous chronic mild stress for 4 weeks, and 3 different stresses were given every day, and the stresses we...

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Abstract

The invention discloses chiral silicon-substituted mesembrine as well as a synthesis method and application thereof, and belongs to the technical field of organosilicon compounds. In the invention, sil-(-)-Mesembranol is a lead compound of a product with comprehensive pharmacological characteristics caused by silicon substitution, and chiral silicon substituted mesembrine is synthesized through control of specific conditions, specific reagents, parameters and the like and can be used for preparing a product for treating depression; or, the chiral silicon substituted mesembrine or pharmaceutically acceptable salts thereof as active ingredients, pharmaceutically acceptable carriers, diluents and excipients form a pharmaceutical composition, which is beneficial to drug development and clinical research.

Description

technical field [0001] The invention relates to a class of chiral silicon-substituted mesembrine, a synthesis method and application, and belongs to the technical field of organosilicon compounds. Background technique [0002] "Silicon substitution" in a narrow sense refers to replacing carbon atoms in a specific drug molecular structure with silicon atoms, and in a broad sense refers to the development of functional small molecule entities such as drug molecules containing silicon atoms. Silicon and carbon have many similarities. Both belong to the elements of the main group IV and have the same number of outermost electrons. Therefore, there are many similarities in the way of bonding. However, there are also some differences between the two elements, such as atomic size, electronegativity, lipophilicity, etc. Experimental studies have shown that silicon has many excellent properties after replacing new drugs, such as stronger drug efficacy, higher selectivity and Less to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08A61P25/24
CPCC07F7/0816C07F7/083A61P25/24
Inventor 宋振雷蒋若天高璐罗干陈玲敏范昱李义
Owner SICHUAN UNIV
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