Application of 0-(1H-tetrazole)ethyl derivative of Cleistanone to preparation of anti-heart-failure medicine

A technology of cleorogenes and derivatives, which is applied in the direction of drug combinations, medical preparations containing active ingredients, and pharmaceutical formulas, etc.

Inactive Publication Date: 2015-08-05
NANJING GUANGKANGXIE BIOLOGICAL MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 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 compound

Method used

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  • Application of 0-(1H-tetrazole)ethyl derivative of Cleistanone to preparation of anti-heart-failure medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Preparation of Example 1 Compound Cleistanone

[0018] The preparation method of compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. –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-(1H-tetrazolyl)ethyl derivatives (III) of 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=100:1, v / v), and...

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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 the Cleistanone derivative to preparation of an anti-heart-failure medicine. A novel Cleistanone derivative is synthesized, and a preparation method of the novel Cleistanone derivative is disclosed. Pharmacology experiments show that the Cleistanone derivative has an anti-heart-failure function and has the value of developing an anti-heart-failure medicine.

Description

technical field [0001] The present invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a Cleistanone derivative, 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.); after the 1990s, it ...

Claims

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Application Information

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IPC IPC(8): A61K31/58A61P9/04C07J63/00
Inventor 王慧罗东君江春平吴俊华
Owner NANJING GUANGKANGXIE BIOLOGICAL MEDICAL TECH
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