Application of composition of Virosaine A piperazinyl and imidazolyl derivatives in antibacterial agents

A technology of antibacterial drugs and compositions, which is applied in the direction of antibacterial drugs, antifungal agents, and medical preparations containing active ingredients.

Inactive Publication Date: 2016-08-31
ZHENJIANG MAKERAO BIOPHARM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the irregular treatment and management of tuberculosis patients, irregular chemotherapy and abuse of anti-tuberculosis drugs, the drug resistance of tuberculosis is becoming more and more serious, and the change of drug resistance tends to be multi-drug resistance at the same time. great difficulty at work

Method used

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  • Application of composition of Virosaine A piperazinyl and imidazolyl derivatives in antibacterial agents
  • Application of composition of Virosaine A piperazinyl and imidazolyl derivatives in antibacterial agents
  • Application of composition of Virosaine A piperazinyl and imidazolyl derivatives in antibacterial agents

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The preparation of embodiment 1 compound Virosaine A

[0018] The preparation method of compound Virosaine A (I) refers to the literature published by Bing-Xin Zhao et al. (Bing-Xin Zhao et al., 2012.Virosaines A and B, Two New Birdcage-Shaped Securinega Alkaloids with an Unprecedented Skeleton from Flueggea virosa.Organic Letters 14(2012) 3096–3099).

[0019]

Embodiment 2

[0020] The synthesis of the O-bromoethyl derivative (II) of embodiment 2 Virosaine A

[0021] Compound I (235 mg, 1.00 mmol) was dissolved in 20 mL of benzene, tetrabutylammonium bromide (TBAB) (0.08 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 5 mL of 50% sodium hydroxide solution. The mixture was stirred at 35 °C for 8 h. After 8 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=100:1.0, v / v), the brown concentrated elution band was collected and the solvent was evaporated to obtain a brown powder of Compound II (261mg, 78%) .

...

Embodiment 3

[0026] The synthesis of the O-(piperazinyl) ethyl derivative (III) of embodiment 3 Virosaine A

[0027] Compound II (171mg, 0.5mmol) was dissolved in 20mL 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=100:1.0, v / v), the brown concentrated elution band was collected and the solvent was evaporated to obtain compound III as a light brown solid (123.2mg, ...

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Abstract

The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a composition, a preparation method and application of the composition in preparing antibacterial agents. The invention discloses a composition and a preparation method thereof. Pharmacological experiments prove that the composition has antibacterial effect and has the value in developing the antibacterial agents.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a composition, 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] Helicobacter pylori (Hp) is a Gram-nega...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/496A61P31/04A61P31/10A61P31/06C07D498/22A61K31/439
CPCA61K31/439A61K31/496C07D498/22A61K2300/00Y02A50/30
Inventor 蒋登旭
Owner ZHENJIANG MAKERAO BIOPHARM TECH CO LTD
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