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Stilbene derivative with nitrogen monoxide donor, and preparation method of derivative

A technology of nitric oxide and stilbene, applied in the direction of organic chemistry, etc., can solve problems such as weak activity, and achieve the effects of strong activity, good promotion and application value, and good application effect.

Inactive Publication Date: 2016-12-07
INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Stilbene compounds have a variety of activities, but none of them are strong. Improving their activities will be the focus of drug development in the future.

Method used

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  • Stilbene derivative with nitrogen monoxide donor, and preparation method of derivative
  • Stilbene derivative with nitrogen monoxide donor, and preparation method of derivative
  • Stilbene derivative with nitrogen monoxide donor, and preparation method of derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0056] Embodiment 1: Preparation of brominated stilbene derivatives

[0057] Add 5.12g of pterostilbene, 1.38g of anhydrous potassium carbonate, and 100ml of acetone into a 250ml three-necked reaction flask, and heat to boiling. When the solution is clear, add 8.6ml of 1,2-dibromoethane dropwise. Reflux reaction for 24h. The solution was suction filtered, and the filtrate was concentrated to obtain an oily product. After separation by silica gel column (120 g of 300-400 mesh silica gel) chromatography (eluent: petroleum ether: ethyl acetate = 8:1), 1.86 g of white pure product was obtained, with a yield of 25.6%.

Embodiment 2

[0058] Embodiment 2: Preparation of brominated stilbene derivatives

[0059] Add 5.12g of pterostilbene, 1.38g of anhydrous potassium carbonate, and 100ml of acetone into a 250ml three-necked reaction flask, and heat to boiling. When the solution is clear, add 12ml of 1,4-dibromoethylbutane dropwise. Reflux reaction for 24h. The solution was suction filtered, and the filtrate was concentrated to obtain an oily product. After separation by silica gel column (100 g of 300-400 mesh silica gel) chromatography (eluent: petroleum ether: ethyl acetate = 8:1), 3.06 g of white pure product was obtained, with a yield of 39.1%.

Embodiment 3

[0060] Embodiment 3: Preparation of brominated stilbene derivatives

[0061] Add 2.56g of pterostilbene, 0.69g of anhydrous potassium carbonate, and 50ml of acetone into a 100ml three-necked reaction flask, heat to boiling, when the solution is clear, add 8ml of 1,6-dibromohexane dropwise, and reflux at 56°C 24h. Suction filtration, and the filtrate was concentrated to obtain an oily product. After separation by silica gel column (100 g of 300-400 mesh silica gel) chromatography (eluent: petroleum ether: ethyl acetate = 8:1), 2.90 g of white pure product was obtained, with a yield of 69.2%.

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Abstract

The invention discloses a stilbene derivative with a nitrogen monoxide donor, and a preparation method of the derivative, and belongs to the technical field of medicine synthesis. The stilbene derivative with a nitrogen monoxide donor is formed through splicing a compound represented by structural formula (I) shown in the description and the nitrogen monoxide donor; in the formula (I), R1-R10 are hydroxyl groups, alkyl groups or alkoxy groups, and at least one of R1-R10 is a hydroxyl group; and the nitrogen monoxide donor is -ONO2. The nitrogen monoxide donor is spliced to a stilbene compound in order to enhance the activity of the stilbene compound, so the stilbene derivative with a nitrogen monoxide donor has very good promotion application values.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, and specifically provides a stilbene derivative with a nitric oxide donor and a preparation method thereof. Background technique [0002] Nitric oxide is a short-lived free radical with a half-life of only a few seconds. Due to its small size and lipophilicity, it easily penetrates cell membranes. It is generated in vivo from L-arginine and oxygen molecules under the catalysis of nitric oxide synthase (NOS). Nitric oxide plays a very important role in mammalian physiology and pathophysiology, such as participating in maintaining the dynamic balance of microvessels and large vessels, nerve signal transduction, regulation of immune inflammation, tumorigenesis and metastasis and other physiological and pathological processes. Insufficient nitric oxide production in the body is often closely related to the formation of various diseases, so exogenous nitric oxide is of great significance for ...

Claims

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Application Information

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IPC IPC(8): C07C205/30C07C205/40
CPCC07C205/30C07C205/40
Inventor 孙捷王兵王晓静李娜孙敬勇王英爱吴忠玉刘腾李慧娟殷姝君王鑫鑫李瑞瑞殷冉冉
Owner INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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