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O-(piperidinyl) ethyl derivative of Cleistanone as well as preparation method and application thereof

A technology of ethyl derivatives and cleistanone, which is applied in the field of preparation of O-ethyl derivatives of cleistanone to achieve good anti-heart failure effect

Inactive Publication Date: 2014-10-15
NORTH CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there is no clinically effective drug for the treatment of heart failure. Most drugs have unavoidable toxic and side effects while relieving the symptoms of heart failure. Search for 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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  • O-(piperidinyl) ethyl derivative of Cleistanone as well as preparation method and application thereof
  • O-(piperidinyl) ethyl derivative of Cleistanone as well as preparation method and application thereof
  • O-(piperidinyl) ethyl derivative of Cleistanone as well as preparation method and application thereof

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] Synthesis of O-bromoethyl derivatives (II) of cleistanone Cleistanone of embodiment 2

[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 ...

Embodiment 3

[0026] Example 3 Synthesis of O-(piperidinyl)ethyl derivative (III) of cleistanone Cleistanone

[0027] 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 piperidine (852 mg, 10 mmol) were added , and the mixture was heated to reflux for 16 h. After the reaction, the reaction solution was poured into 20 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-(piperidinyl)ethyl derivative of Cl...

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry, particularly to an O-(piperidinyl) ethyl derivative of Cleistanone as well as a preparation method for the O-(piperidinyl) ethyl derivative of the Cleistanone and the application of the O-(piperidinyl) ethyl derivative of the Cleistanone in preparing drugs for resisting heart failure. The invention synthesizes a novel O-(piperidinyl) ethyl derivative of the Cleistanone and discloses the preparation method thereof. Pharmacological experiment results show that the O-(piperidinyl) ethyl derivative of the Cleistanone has the function of resisting heart failure and has the value of developing drugs for resisting heart failure.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to O-(piperidinyl)ethyl derivatives of cleistanone, a preparation method and uses 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.); after the 1990s...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/58A61P9/04
Inventor 吴俊艺王慧吴俊华
Owner NORTH CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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