Preparation method and application of cleistanone derivative

A technology of cleusenone and its derivatives, applied in the direction of drug combinations, steroids, and resistance to vector-borne diseases, can solve the problems of non-standard treatment and management of tuberculosis patients, difficulties in tuberculosis prevention and control, and achieve good antibacterial effects Effect

Inactive Publication Date: 2016-11-23
虞定生
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Preparation method and application of cleistanone derivative
  • Preparation method and application of cleistanone derivative
  • Preparation method and application of cleistanone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation of Example 1 Compound Cleistanone

[0026] The preparation method of compound Cleistanone (I) refers to the method published by VanTrinhThiThanh et al. (VanTrinhThiThanh et al., 2011.Cleistanone:ATriterpenoidfromCleistanthusindochinensiswithaNewCarbonSkeleton.Volume2011, Issue22, pages4108-4111, August2011).

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

[0035] Compound II (273mg, 0.5mmol) was dissolved in 20mL of acetonitrile, anhydrous potassium carbonate (345mg, 2.5mmol), potassium iodide (84mg, 0.5mmol) and dimethylamine (900mg, 20mmol) were added thereto, and the mixture was heated to reflux for 16h . 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. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1, v / v), and the light yellow concentrated elution band was collected to obtain compound III as a light yellow solid (160.7 mg, ...

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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 antibacterial drugs. The novel cleistanone derivative is synthesized, and the preparation method of the cleistanone derivative is disclosed. Pharmacological experiments show that the cleistanone derivative has an antibacterial effect and an antibacterial drug development value.

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] 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61P31/04A61P31/10A61P1/04A61P31/06
CPCC07J63/00C07J63/008Y02A50/30
Inventor 不公告发明人
Owner 虞定生
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