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Schizandrin, schisanhenol and schisandrin-b derivates and application thereof

A technology of schisandrin A and schisandrin B, which is applied in the field of schisandrin and schisandrin derivatives, schisandrin A, can solve the problems of drug withdrawal rebound and achieve low price, significant protective effect, and definite curative effect

Inactive Publication Date: 2012-08-08
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the 1970s and 1990s in our country, a large number of scientists, including academician Liu Gengtao of the Beijing Institute of Materia Medica, Chinese Academy of Medical Sciences, through unremitting efforts, successfully developed a new drug for chronic hepatitis, bifendate ( DDB) and bicyclol have brought good news to the majority of patients with liver diseases in clinical practice, but the fly in the ointment is that drug withdrawal will cause rebound and other phenomena

Method used

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  • Schizandrin, schisanhenol and schisandrin-b derivates and application thereof
  • Schizandrin, schisanhenol and schisandrin-b derivates and application thereof
  • Schizandrin, schisanhenol and schisandrin-b derivates and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: Schisandrin and Schisandrin C 4 、C 11 double chlorination

[0018] Weigh 0.25 mmol of schisandrin (or schisandrin) and 0.52 mmol of N-chlorosuccinimide (NCS) in a dry 25 mL round bottom flask, and then add 5 mL of methanol into the round bottom flask (analytical pure), stirred at room temperature for 1 h, added water to terminate the reaction, extracted three times with chloroform, and the chloroform layer was washed with Na 2 SO 4 Dry, filter, concentrate the organic layer, and prepare compound 1 (yield 44.4%) and compound 2 ( The yield is 98.4%).

[0019]

[0020] EI-MS: m / z 468 [M] + ; 1 H-NMR (CDCl 3 , 400 MHz) δ (ppm): 6.06 (2H, m), 3.94 (6H, s), 3.76 (3H, s), 3.56 (3H, s), 2.48 (1H, m), 2.27 (2H, m), 2.01 (1H, m), 1.77 (1H, m), 1.62 (1H, m), 1.04 (3H, d, J = 7.2 Hz), 0.84 (3H,d, J = 7.2 Hz); 13 C-NMR (CDCl 3 , 100 MHz) δ (ppm): 150.4(s), 149.4(s), 145.6(s), 144.7(s), 139.5(s), 135.0(s), 135.0(s), 133.0(s), 127.1(s), 124.6 (s), ...

Embodiment 2

[0023] Embodiment 2: Schisandrin and Schizandrin C 4 、C 11 double bromination reaction

[0024] Weigh 0.12 mmol of schisandrin (or schisandrin B) into a dry 25 mL round bottom flask, then add an appropriate amount of water-saturated CCl 4 solution, after the sample is dissolved, add 4 drops of bromine (Br 2 ), the mixed system was stirred at room temperature in the dark for 1 h, and then 10 % Na was added dropwise to the reaction system 2 S 2 o 3 , fully stirred until the color of bromine-free water, the reaction solution was extracted three times with chloroform, and the chloroform layer was extracted with Na 2 SO 4 Dry, filter, concentrate the organic layer, and prepare compound 3 (yield: 98%) and compound 4 by preparative thin layer chromatography (petroleum ether-ethyl acetate = (5-3): 1) (97.6% yield).

[0025]

[0026] EI-MS: m / z 560 [M] + ; 1 H-NMR (CDCl 3 , 400 MHz) δ(ppm): 6.05 (2H, m), 3.90 (6H, s), 3.73 (3H, s), 3.54 (3H, s), 2.46 (2H, m), 2.35 (2H...

Embodiment 3

[0029] Embodiment 3: Schisandrin A C 4 、C 11 double bromination reaction

[0030] Weigh 0.25 mmol of Schisandrin A and 0.62 mmol of N-chlorosuccinimide (NBS) respectively in a dry 25 mL round bottom flask, add 5 mL of methanol (analytical grade) into the round bottom flask, and store at room temperature The reaction was stirred for 1 h, extracted three times with water-chloroform, and the chloroform layer was washed with Na 2 SO 4 Dry, filter, concentrate the organic layer, and prepare compound 5 (95.9% yield) by preparative thin-layer chromatography (petroleum ether-ethyl acetate = 6:1 as the developing solvent).

[0031]

[0032] EI-MS: m / z 590 [M] + ; 1 H-NMR (CDCl 3 , 400 MHz) δ (ppm): 3.88 (12H, s), 3.52 (3H, s), 3.39 (3H, s), 3.08 (1H, m), 2.95 (1H, d, J = 14.0 Hz), 2.64 (2H, m), 1.88 (1H, m), 1.26 (3H, s), 0.82 (3H, d, J = 7.2 Hz); 13 C-NMR (CDCl 3 , 100 MHz) δ (ppm): 177.9(s), 150.8(s), 150.5(s), 150.3(s), 144.8(s), 144.4(s), 134.7(s), 133.3(s)...

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Abstract

The invention discloses schizandrin, schisanhenol and schisandrin-b derivates and an application thereof in the preparation of drugs for treating liver cell injury. Compared with the prior art, the schizandrin, the schisanhenol and the schisandrin-b are subjected to structural modification and transformation, 4 substitution positions and / or 11 substitution positions are respectively halogenated and / or oxidized to generate derivates with a structure of a general formula (1), and the derivates have a remarkable protection effect on CC14 human liver HL-7702 cell injury and can serve as candidate compounds of novel anti-liver injury drugs with low screening price and definite and relapse-free treatment effect, particularly anti-chemical injury drugs.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to derivatives of schisandrin A, schisandrin and schisandrin B and uses thereof. Background technique [0002] Hepatocyte injury is the common pathological basis of various liver diseases, including liver injury caused by three major factors: viruses, alcohol and chemical substances. Among them, the liver injury caused by chemical hepatotoxic substances, that is, chemical liver injury, is an important initiating link for various liver diseases, and has become the second largest cause of liver disease after viral liver injury. -More than 1,000 kinds of Chinese and Western medicines and various chemicals can cause different degrees of liver disease. According to reports at home and abroad, 20% of fulminant liver failure is caused by chemical drugs. In recent years, chemical liver injury has been increasing, which seriously threatens people's life and health. However, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/70C07C43/23C07C41/22C07C41/01C07C41/16C07C41/18C07C69/157C07C67/00C07C67/08C07C50/34C07C46/06A61K31/357A61K31/122A61K31/09A61K31/222A61P1/16
Inventor 穆淑珍郝小江贺涛时京珍
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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