Application of Cleistanone O-(morpholinyl)ethyl derivative in preparation of anti-hypoxia drugs

A technology of ethyl derivatives and anti-hypoxic drugs, which is applied in the direction of drug combinations, medical preparations containing active ingredients, anti-toxic agents, etc., to achieve a good anti-hypoxic effect

Active Publication Date: 2014-12-10
徐州三禾饲料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Currently, there is no clinically effective drug for the treatment of heart failure. Most of the drugs have unavoidable side effects while relieving the symptoms of heart failure. 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 are of great value

Method used

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  • Application of Cleistanone O-(morpholinyl)ethyl derivative in preparation of anti-hypoxia drugs
  • Application of Cleistanone O-(morpholinyl)ethyl derivative in preparation of anti-hypoxia drugs
  • Application of Cleistanone O-(morpholinyl)ethyl derivative in preparation of anti-hypoxia drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 Preparation of Compound Cleistanone

[0019] The preparation method of the compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. –4111, August 2011).

[0020]

Embodiment 2

[0021] Example 2 Synthesis of O-Bromoethyl Derivatives (II) of Cleistanone

[0022] 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%).

[0023] 1H NMR (500MHz, DMSO-d 6...

Embodiment 3

[0027] Example 3 Synthesis of O-(morpholinyl) ethyl derivatives (III) of cleistanone Cleistanone

[0028] Compound II (273 mg, 0.5 mmol) was dissolved in 20 mL of acetonitrile, anhydrous potassium carbonate (345 mg, 2.5 mmol), potassium iodide (84 mg, 0.5 mmol) and morpholine (1742 mg, 20 mmol) were added thereto, and the mixture was heated to reflux for 8 h. After the reaction was completed, the reaction solution was poured into 30 mL of 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. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:0.5, v / v), and the yellow concentrated elution band was collected to obtain the yellow color of the O-(morpholino)e...

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Abstract

The invention relates to the field of organic synthesis and pharmaceutical chemistry and particularly relates to a Cleistanone O-(morpholinyl)ethyl derivative, a preparation method thereof and application thereof in the preparation of anti-hypoxia drugs. According to the invention, a novel Cleistanone O-(morpholinyl)ethyl derivative is synthesized, and a preparation method of the novel Cleistanone O-(morpholinyl)ethyl derivative is disclosed. Shown by pharmacological experiments, the Cleistanone O-(morpholinyl)ethyl derivative disclosed by the invention has an anti-hypoxia effect and has a value in the development of the anti-hypoxia drugs.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to an O-(morpholinyl) ethyl derivative of cleistanone, a preparation method and an application thereof. Background technique [0002] Oxygen is an important condition for the survival of human beings and many organisms. Hypoxia refers to the insufficient supply of oxygen required by the body's life activities. Oxygen and hypoxia are the most important key factors in life activities, and are important topics in the basic theory of life sciences. The formation of hypoxia can be divided into three categories: the first category is that the oxygen content of the external environment is reduced, so that the normal physiological activities cannot take in enough oxygen, such as plateau and aviation hypoxia; the second category is the normal oxygen level caused by diseases, etc. Can not fully reach the body, causing hypoxia in the heart, brain and respiratory syst...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/58A61P39/00
Inventor 王慧黄蓉吴俊华
Owner 徐州三禾饲料有限公司
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