O-(piperazinyl) ethyl derivative of cleistanone, preparation method of O-(piperazinyl) ethyl derivative of cleistanone and use of O-(piperazinyl) ethyl derivative of cleistanone

A technology of cleistanone and derivatives, which is applied in the field of preparation of O-ethyl derivatives of cleistanone, can solve problems such as indigestion and destruction of bacterial flora in the digestive tract, and achieve good antibacterial effect

Active Publication Date: 2015-03-25
NANJING UNIV
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  • Application Information

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Problems solved by technology

The most important factor affecting triple therapy is considered to be the resistance of Hp to antibacterial agents; another serious problem is ...

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  • O-(piperazinyl) ethyl derivative of cleistanone, preparation method of O-(piperazinyl) ethyl derivative of cleistanone and use of O-(piperazinyl) ethyl derivative of cleistanone
  • O-(piperazinyl) ethyl derivative of cleistanone, preparation method of O-(piperazinyl) ethyl derivative of cleistanone and use of O-(piperazinyl) ethyl derivative of cleistanone
  • O-(piperazinyl) ethyl derivative of cleistanone, preparation method of O-(piperazinyl) ethyl derivative of cleistanone and use of O-(piperazinyl) ethyl derivative of cleistanone

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Embodiment 1

[0025] Preparation of Example 1 Compound Cleistanone

[0026] 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).

[0027]

Embodiment 2

[0028] Synthesis of O-bromoethyl derivatives (II) of cleistanone Cleistanone of embodiment 2

[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 ...

Embodiment 3

[0034] Synthesis of O-(piperazinyl) ethyl derivative (III) of cleistanone Cleistanone of embodiment 3

[0035] Compound II (273mg, 0.5mmol) was dissolved in 30mL of acetonitrile, anhydrous potassium carbonate (690mg, 5.0mmol), potassium iodide (168mg, 1.0mmol) and anhydrous piperazine (3446mg, 40mmol) were added thereto, and the mixture was heated to reflux 3h. After the reaction, the reaction solution was poured into ice water, extracted twice 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=100:1.5, v / v), and the light brown concentrated elution band was collected to obtain compound III as a light brown solid (196.9 mg, 71%).

[003...

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry, and particularly relates to an O-(piperazinyl) ethyl derivative of cleistanone, a preparation method of the O-(piperazinyl) ethyl derivative of cleistanone and use of the O-(piperazinyl) ethyl derivative in preparing an antibacterial drug. In the invention, the novel cleistanone derivative is synthesized and the preparation method of the novel cleistanone derivative is disclosed. A pharmacology experiment shows that the cleistanone derivative has an antibacterial effect and a value for developing the antibacterial drug.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to O-(piperazinyl)ethyl derivatives of cleistanone, a preparation method and uses 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] In recent years...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/58A61P31/04A61P31/06A61P31/10
CPCC07J63/008Y02A50/30
Inventor 王慧吴俊艺黄蓉吴俊华
Owner NANJING UNIV
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