Application of o-(morpholinyl)ethyl derivatives of cleistanone cleistanone in the preparation of antibacterial drugs

A technology of ethyl derivatives and cleus genus, which is applied in the direction of antibacterial drugs, antifungal agents, and medical preparations containing active ingredients, etc., to achieve good antibacterial effect and strong antifungal activity against human body

Inactive Publication Date: 2016-10-19
QINGDAO MUNICIPAL HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, there is no clinically effective drug for antibacterial treatment, and most drugs have unavoidable toxic and side effects while relieving antibacterial symptoms. Find compounds or lead compounds from natural products and carry out structural modification to obtain their derivatives, so as to obtain high-efficiency and low-efficiency drugs. Potential drugs for poisons are of great value

Method used

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  • Application of o-(morpholinyl)ethyl derivatives of cleistanone cleistanone in the preparation of antibacterial drugs
  • Application of o-(morpholinyl)ethyl derivatives of cleistanone cleistanone in the preparation of antibacterial drugs
  • Application of o-(morpholinyl)ethyl derivatives of cleistanone cleistanone in the preparation of antibacterial drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Preparation of Compound Cleistanone

[0026] The preparation method of compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. (Van Trinh Thi Thanh et al., 2011.Cleistanone: A Triterpenoid from Cleistanthus indochinensis with a New Carbon Skeleton. 4111, August2011) approach.

[0027]

Embodiment 2

[0028] Example 2 Synthesis of O-Bromoethyl Derivatives (II) of Cleistanone

[0029] 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%).

[0030] 1H NMR (500MHz, DMSO-d 6...

Embodiment 3

[0034] Example 3 Synthesis of O-(morpholinyl) ethyl derivatives (III) of cleistanone Cleistanone

[0035] 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 antibacterial 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 antibacterial effect and has a value in the development of the antibacterial 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] The spread of pathogenic bacteria and the enhancement of drug resistance seriously threaten human health and life. Antibacterial drugs have been widely used as routine drugs in the treatment of AIDS, organ transplantation and chronic wasting diseases (such as cancer, diabetes, uremia, etc.) Treatment, although antibacterial agents currently used clinically (such as ketoconazole, amikacin, gentamicin, vigorconazole, itraconazole, terbinafine, amphotericin, fluconazole, etc.) The curative effect on skin and superficial infection is good, but these antibacterial drugs have strong accumulation toxicity, often causing liver and kidney damage, gastrointestinal irritation, dizziness, allergies, etc. one of the hotspots. [0003] He...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/58A61P31/04A61P31/06A61P31/10
CPCY02A50/30
Inventor 谢方瑜解祥军
Owner QINGDAO MUNICIPAL HOSPITAL
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