Schisanhenol derivative, preparation method and application thereof

A technology of schisandrin and its derivatives, which is applied in the field of schisandrin derivatives and its preparation, and can solve the problems of affecting drug efficacy, poor water solubility, unfavorable compound transport, etc.

Active Publication Date: 2020-09-08
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its poor water solubility, it is not conducive to the transport of compounds in body fluids, reaching the site of action and binding to receptors, thus affecting its efficacy

Method used

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  • Schisanhenol derivative, preparation method and application thereof
  • Schisanhenol derivative, preparation method and application thereof
  • Schisanhenol derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Embodiment 1: The concrete preparation method of intermediate I-III is as follows:

[0077] Intermediate Ⅰ:

[0078]

[0079] Reaction steps: Weigh 200mg (0.50mmoL) schisandrin in a 50mL dry round bottom flask, add appropriate amount of methanol to dissolve the sample completely, then weigh 100mg (0.75mmoL) NCS in the bottle, stir and react at 20°C for 6h, wait for TLC After detecting that the reaction is complete, add water to terminate the reaction, extract 3 times with ethyl acetate, concentrate the ethyl acetate layer, and pass through silica gel column chromatography under reduced pressure (eluent is petroleum ether-ethyl acetate (V / V)=10 ︰1), and intermediate Ⅰ (197.0 mg, yield 90.8%) was prepared.

[0080] Intermediate II:

[0081]

[0082] Reaction steps: Weigh 100mg (0.25mmoL) schisandra phenol and 70mg (0.52mmoL) NCS respectively in a dry 25mL round bottom flask, then add 5mL of methanol (analytical grade) to the round bottom flask, stir and react for ...

Embodiment 2

[0087] Embodiment 2: the preparation method of schisandrin derivative C1:

[0088]

[0089] Reaction steps: Weigh 100mg of Intermediate I (0.23mmoL), 10mg of DMAP (0.08mmoL) and 59mg (0.34mmoL) of p-methoxybenzoyl chloride in a 25mL dry round bottom flask, then add 13mg of EDC·HCl (0.069 mmoL), vacuumize for 10min, under the protection of nitrogen, place in an ice-water bath, add 4mL of dry dichloromethane (DCM) under stirring, remove the ice-water bath, stir for 3h under the protection of nitrogen at room temperature, and wait for the reaction to be detected by thin-layer chromatography After completion, add water to terminate the reaction, extract 3 times with chloroform, concentrate the organic layer, and prepare C1 (121mg , the yield is 92.6%).

[0090] White solid; ESI-MS m / z: 593[M+Na] + ; 1 H-NMR (CDCl 3 , 400MHz) δ: 7.90 (2H, d, J = 8.9Hz), 6.83 (2H, d, J = 8.9Hz), 6.43 (1H, s), 3.98 (3H, s), 3.88 (3H, s), 3.82(3H,s), 3.79(3H,s), 3.70(3H,s), 3.53(3H,s), 2.37(2H...

Embodiment 3

[0091] Embodiment 3: the preparation method of schisandrin derivative C2:

[0092]

[0093] Reaction steps: Weigh 100mg of intermediate Ⅰ (0.22mmoL), 10mg of DMAP (0.08mmoL) and 57mg (0.34mmoL) of cinnamoyl chloride in a 25mL dry round bottom flask, then add 13mg of EDC·HCl (0.069mmoL), and vacuumize 10min, under nitrogen protection, placed in an ice-water bath with stirring, added 4 mL of dry dichloromethane (DCM) to remove the ice-water bath, stirred at room temperature under nitrogen protection, and stirred for 6 hours. After TLC detected that the reaction was complete, add water to terminate the reaction, chloroform Extracted 3 times, concentrated the organic layer, and prepared C2 (118 mg, yield 91.5%) by silica gel column chromatography under reduced pressure (eluent: petroleum ether-ethyl acetate (V / V)=5:1).

[0094] White solid; ESI-MS m / z: 589[M+Na] + ; 1 H-NMR (CDCl 3 , 500MHz) δ: 7.63(1H, m), 7.53(1H, m), 7.53(1H, m), 7.40(1H, m), 7.39(1H, m), 7.38(1H, m), 3.9...

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PUM

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Abstract

The invention provides a schisanhenol derivative with structures represented by general formulas (1), (2), (3) and (4), a preparation method and application thereof. According to the schisanhenol derivative, an active natural product schisanhenol is used as a substrate, and related groups are introduced to synthesize a series of schisanhenol derivatives; it is disclosed for the first time that theschisanhenol derivative has an obvious protective effect on concanavalin A induced HL-7702 human hepatocyte immune injury, it is prompted that the compound can be used for preparing liver protectiondrugs, and the liver protection effect is further explained through biological tests; schisanhenol in the raw materials mainly comes from dried ripe fruits of schisandra chinensis, and is rich in content, high in quality and low in price; and the preparation process is simple in steps, easy to operate and beneficial to large-scale production.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to schisandrin derivatives and their preparation methods and applications. Background technique [0002] The liver is one of the most important organs of human beings, and liver damage has become one of the main factors threatening human life and health. Liver cell damage is mainly caused by three major factors: viruses, alcohol and chemical substances, and is the common pathological basis of various liver diseases. The long-term existence of immune liver damage is an important factor for the development of liver cirrhosis, liver fibrosis and liver tumors. The initiating link is the inflammation of liver tissue caused by immune response, which often exists in liver diseases such as viral hepatitis and autoimmune hepatitis. [0003] Modern medicine has conducted in-depth research on liver damage caused by various inducements. The mechanism of liver damage has been explor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/57C07C69/78C07C67/08C07C201/12C07C69/92C07D213/803C07D333/40C07C69/618C07C323/59C07C319/20C07C303/30C07C309/73C07C205/37C07C211/61C07C209/36A61P37/02A61P1/16
CPCC07C205/57C07C69/78C07C69/92C07D333/40C07C69/618C07C323/59C07C309/73C07C205/37C07C211/61A61P37/02A61P1/16
Inventor 邓璐璐穆淑珍程莎莎郝小江丁同同李江李艳梅范艳华
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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