Application of O-(imidazolyl) ethyl derivative of cleistanone in preparation of antibacterial drug

A technology of ethyl derivatives and cleus genus, which is applied in the direction of antibacterial drugs, drug combinations, antifungal agents, etc., to achieve strong anti-fungal activity and good antibacterial effect

Active Publication Date: 2015-04-22
煌途医药(无锡)有限公司
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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-(imidazolyl) ethyl derivative of cleistanone in preparation of antibacterial drug
  • Application of O-(imidazolyl) ethyl derivative of cleistanone in preparation of antibacterial drug
  • Application of O-(imidazolyl) ethyl derivative of cleistanone in preparation of antibacterial drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Preparation of 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] 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-(imidazolyl)ethyl derivatives (III) of cleistanone Cleistanone

[0035] Compound II (273 mg, 0.5 mmol) was dissolved in 35 mL of acetonitrile, anhydrous potassium carbonate (690 mg, 5.0 mmol), potassium iodide (252 mg, 1.5 mmol) and imidazole (870 mg, 10 mmol) were added thereto, and the mixture was heated to reflux for 3 h. After the reaction was completed, the reaction solution was poured into 45 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=100:0.2, v / v), and the brown concentrated elution band was collected to obtain the brown solid of the O-(imidazolyl)ethyl ...

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry, and particularly relates to an O-(imidazolyl) ethyl derivative of cleistanone, as well as a preparation method and application thereof in preparation of an antibacterial drug. The invention synthesizes a novel O-(imidazolyl) ethyl derivative of the cleistanone and discloses the preparation method thereof. Pharmacological experiments show that the O-(imidazolyl) ethyl derivative of the cleistanone has an antibacterial effect and has a value for developing antibacterial drugs.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to an O-(imidazolyl) ethyl derivative of Cleustanone, a preparation method and an application thereof. Background technique [0002] Helicobacter pylori (Hp) is a Gram-negative spiral bacterium. Studies have shown that Helicobacter pylori is the main cause of acute and chronic gastritis and gastric and duodenal ulcers, and may be related to gastric cancer and gastric mucosa-associated lymphoid tissue (MALT) malignant lymphoma. Recently, the World Health Organization classified Hp as a class I carcinogen, which plays a leading role in the development of gastric cancer. The current popular treatment for Hp infection is the triple therapy of taking proton pump inhibitor (PPI) plus two kinds of antibiotics (clarithromycin, amoxicillin, tetracycline, metronidazole, etc.) at the same time. The most important factor affecting triple therapy is considered to be th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/58A61P31/10A61P31/04A61P31/06A61P1/04C07J63/00
CPCA61K31/58C07J63/008Y02A50/30
Inventor 黄蓉吴俊艺吴俊华
Owner 煌途医药(无锡)有限公司
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