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Application of O-(1H-tetrazole)ethyl derivative of Cleistanone to preparation of liver injury prevention and treatment medicine

A technology for ethyl derivatives and liver damage, which is applied in the field of preparation of O-ethyl derivatives of Cleistanone, can solve the problems of high toxicity, aggravation, and low safety of liver damage, and achieve good resistance to liver damage Effect

Inactive Publication Date: 2015-08-05
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

4. Other reasons: primary and secondary liver tumors, liver congestion caused by cardiac insufficiency, certain congenital liver diseases, high-priced intravenous nutrition, etc., can all cause liver damage to varying degrees. The early manifestations of these liver damage are often Elevation of ALT (transaminase) or bilirubin, if the cause is not eliminated, the liver damage will be further aggravated
[0003] The existing drugs for the treatment of liver damage have the problems of high toxicity and low safety. It is of great value to find compounds or lead compounds from natural products and carry out structural modification to obtain their derivatives, so as to obtain potential drugs with high efficiency and low toxicity

Method used

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  • Application of O-(1H-tetrazole)ethyl derivative of Cleistanone to preparation of liver injury prevention and treatment medicine
  • Application of O-(1H-tetrazole)ethyl derivative of Cleistanone to preparation of liver injury prevention and treatment medicine
  • Application of O-(1H-tetrazole)ethyl derivative of Cleistanone to preparation of liver injury prevention and treatment medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 Preparation of Compound Cleistanone

[0018] The preparation method of the compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. , pages 4108–4111, August 2011).

[0019]

Embodiment 2

[0020] Example 2 Synthesis of O-Bromoethyl Derivatives (II) of Cleistanone

[0021] Compound I (440 mg, 1.00 mmol) was dissolved in 10 mL of benzene, and tetrabutylammonium bromide (TBAB) (0.04 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 25 °C for 24 h. After 24 hours, the reaction solution was poured into ice water, extracted twice with dichloromethane immediately, and the organic phase solutions were combined. Then the organic phase solution was washed with water and saturated brine three times successively, then dried with anhydrous sodium sulfate, and finally concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1, v / v), and the yellow concentrated elution band was collected to obtain compound II as a yellow solid (344 mg, 63%).

[0022] 1H NMR (500MHz, DMSO-d 6...

Embodiment 3

[0026] Example 3 Synthesis of O-(1H-tetrazolyl)ethyl derivatives (III) of cleistanone Cleistanone

[0027] Compound II (273mg, 0.5mmol) was dissolved in 15mL of acetonitrile, anhydrous potassium carbonate (345mg, 2.5mmol), potassium iodide (84mg, 0.5mmol) and 1H-tetrazolium (1401mg, 20mmol) were added thereto, and the mixture was heated Reflux 10h. After the reaction was completed, the reaction solution was poured into ice water, extracted three times with an equal amount of dichloromethane, and the organic phases were combined. The combined organic phases were successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to obtain a crude product. Because of tautomerism, two substitution products, 1H-tetrazolyl and 2H-tetrazolyl, will be generated under the reaction conditions. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:...

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry, in particular to a Cleistanone derivative, a preparation method and application of a O-(1H-tetrazole)ethyl derivative of Cleistanone to preparation of a liver injury prevention and treatment medicine. A novel O-(1H-tetrazole)ethyl derivative of Cleistanone is synthesized, and a preparation method of the novel 0-(1H-tetrazole)ethyl derivative of Cleistanone is disclosed. Pharmacology experiments show that the O-(1H-tetrazole)ethyl derivative of Cleistanone has a liver injury prevention and treatment function and has the value of developing a liver injury prevention and treatment medicine.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to O-(1H-tetrazolyl)ethyl derivatives of cleistanone, a preparation method and uses thereof. Background technique [0002] There are multiple reasons for causing liver damage: 1. Viral infection: caused by a variety of hepatitis viruses, with strong infectivity, complex transmission routes, wide epidemic range, and high incidence rate. 2. Drugs or chemical poisons: Many drugs and chemical poisons can cause liver damage, drug-induced hepatitis or toxic hepatitis. 3. Alcoholism: Alcohol damages the liver very seriously. The consequences of the damage include alcoholic hepatitis, alcoholic fatty liver, and alcoholic cirrhosis, mainly due to the toxicity of alcohol (ethanol) and its metabolite acetaldehyde on liver cells. caused by direct damage. 4. Other reasons: primary and secondary liver tumors, liver congestion caused by cardiac insufficiency, certain con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/58A61P1/16
Inventor 吴俊华王慧黄蓉
Owner NANJING UNIV
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