Application of Cleistanone O-(morpholinyl)ethyl derivative in preparation of heart failure resisting drugs

A technology of ethyl derivatives and cylinone, which is applied in the directions of drug combination, medical preparations containing active ingredients, pharmaceutical formulas, etc., to achieve the effect of good anti-heart failure effect

Active Publication Date: 2014-12-10
北京宽厚医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 compoun

Method used

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  • Application of Cleistanone O-(morpholinyl)ethyl derivative in preparation of heart failure resisting drugs
  • Application of Cleistanone O-(morpholinyl)ethyl derivative in preparation of heart failure resisting drugs
  • Application of Cleistanone O-(morpholinyl)ethyl derivative in preparation of heart failure resisting 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-d6) ...

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 heart failure resisting 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 a heart failure resisting effect and has a value in the development of the heart failure resisting 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] Heart failure (HF) refers to a pathophysiological state in which abnormal cardiac function causes the pumping volume of the heart to fail to meet the needs of tissue metabolism. The etiology is cardiac overload, limited relaxation of the myocardium itself, and initial myocardial damage caused by any reason; while infection, anemia, pregnancy, childbirth, cardiac rhythm disorder, pulmonary embolism, hyperthyroidism, diabetes, and heart inhibitors induce aggravated HF. Pathogenesis In the past, it was believed that the mechanism of HF development was abnormal hemodynamics; in the late 1980s, it was recognized that the activation of neuroendocrine hormones played an important role (activation of sympathetic ↑ NE ↑ RAS ↑ etc.); af...

Claims

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Application Information

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IPC IPC(8): A61K31/58A61P9/04
Inventor 吴俊艺黄蓉吴俊华
Owner 北京宽厚医药科技有限公司
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