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Application of composition of tetrahydropyrrolyl and morpholinyl derivatives of Virosaine A in antibacterial medicines

A technology of antibacterial drugs and compositions, which is applied in the direction of antibacterial drugs, drug combinations, antifungal agents, etc., and can solve problems such as difficulties in tuberculosis prevention and control, and non-standard treatment and management of tuberculosis patients

Inactive Publication Date: 2016-09-07
NANJING FUHAIAOSAI PHARMA 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 tetrahydropyrrolyl and morpholinyl derivatives of Virosaine A in antibacterial medicines
  • Application of composition of tetrahydropyrrolyl and morpholinyl derivatives of Virosaine A in antibacterial medicines
  • Application of composition of tetrahydropyrrolyl and morpholinyl derivatives of Virosaine A in antibacterial medicines

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Experimental program
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Effect test

Embodiment 1

[0018] The preparation of embodiment 1 compound Virosaine A

[0019] The preparation method of compound Virosaine A (I) refers to the literature (Bing-Xin Zhao et al., 2012. Virosaines A and B, Two New Birdcage-Shaped Securinega Alkaloids with an Unprecedented Skeleton from Flueggea virosa. Organic Methods of Letters 14 (2012) 3096–3099).

[0020]

Embodiment 2

[0021] The synthesis of the O-bromoethyl derivative (II) of embodiment 2 Virosaine A

[0022] 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

[0027] Example 3 Synthesis of O-(tetrahydropyrrolyl) ethyl derivatives (III) of Virosaine A

[0028] Compound II (171 mg, 0.5 mmol) was dissolved in 15 mL of acetonitrile, anhydrous potassium carbonate (345 mg, 2.5 mmol), potassium iodide (84 mg, 0.5 mmol) and pyrrolidine (1420 mg, 20 mmol) were added thereto, and the mixture was heated to reflux for 1 h. 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 yellow concentrated elution band was collected to obtain the O-(tetrahydropyrrolyl)ethyl derivative of Virosaine A Compoun...

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Abstract

The invention discloses an application of a composition of tetrahydropyrrolyl and morpholinyl derivatives of Virosaine A in antibacterial medicines. The invention relates to the fields of organic synthesis and medicinal chemistry, and in particular to the composition, a preparation method and the application of the composition in preparing the antibacterial medicines. The invention discloses the composition and the preparation method thereof. Pharmacological experiments show that the composition disclosed by the invention has an antibacterial effect, and the composition has a value of developing the antibacterial medicines.

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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IPC IPC(8): A61K31/5377A61K31/439C07D498/22A61P31/04A61P31/06A61P31/10A61P1/04
CPCA61K31/439A61K31/5377C07D498/22A61K2300/00Y02A50/30
Inventor 王卓婷
Owner NANJING FUHAIAOSAI PHARMA CO LTD
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