Coumarin derivative and its preparation method and application

A technology for coumarin derivatives and cigarettes, applied in the field of coumarin derivatives and their preparation, can solve problems such as tissue damage and oxidative stress, and achieve the effects of strong anti-oxidation, inhibition of free radical scavenging and harm reduction

Active Publication Date: 2015-12-02
CHINA TOBACCO GUANGDONG IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when the human body is attacked by more free radicals from outside, the metabolic balance of free radical production and removal is broken, and oxygen stress occurs, which leads to tissue damage in the human body and causes diseases.

Method used

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  • Coumarin derivative and its preparation method and application
  • Coumarin derivative and its preparation method and application
  • Coumarin derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthesis of Example 1 Compound

[0051] The design synthetic route is as follows:

[0052] (1) Method 1:

[0053]

[0054] The specific preparation steps are as follows: first add 40 mL of anhydrous methanol as a solvent in a 100 mL conical flask, add coumarin reactants and hydroxy aldehydes at a molar ratio of 1:2, stir under reflux for 3 to 4 hours, and use TLC (thin Layer chromatography method) to track the reaction process, when the reaction is complete, a solid will precipitate. Let stand, filter with suction, wash the solid three times with anhydrous methanol, and dry by infrared to obtain the product.

[0055] (2) Or method 2:

[0056]

[0057] The specific preparation steps are as follows: first add 40 mL of anhydrous methanol as a solvent in a 100 mL conical flask, add coumarin and aldehyde at a molar ratio of 1:2, then add 0.5 mL of triethylamine, and stir for 8 hours at room temperature. Use TLC (Thin Layer Chromatography) to track the progress of the reaction, and...

Embodiment 2

[0077] Example 2 Research experiment to inhibit and clear the activity of free radicals

[0078] References [Jin Ming, Cai Yaxin, etc. Phenanthroline-Fe 2+ Oxidation method to detect H 2 O 2 , Fe 2+ The generated hydroxyl radicals, Progress in Biochemistry and Biophysics, 1996,23(6):553-555] introduced the method, and used Fenton reaction to complete the determination.

[0079] Operation steps: In a 10mL volumetric flask, add 5mmol / L 1.5mL o-phenanthroline, pH 7.4, 0.5mol / L phosphate buffer 3mL, 7.5mmol / L FeSO 4 1.0mL, mix immediately. Then add 3mL of the sample to be tested, 0.1%H 2 O 2 1.0mL, distilled water to make up to 10mL. After mixing, heat in a water bath at 37°C for 1 hour, and then measure the absorbance at a wavelength of 510nm.

[0080] Calculation method: free radical scavenging rate EC 50 = (A s -A 0 ) / (A 1 -A 0 )

[0081] Among them, A s To add the sample to be tested and H 2 O 2 The measured absorbance of the solution, A 1 For no sample and H 2 O 2 The measured abso...

Embodiment 3

[0085] Example 3 Experiments using cigarettes

[0086] Select a certain brand of cigarette leaf components into two groups, and add the compound of the invention to the shredded tobacco during the process of rolling the shredded tobacco. The amount of added compound accounts for 0.01% of the total mass of cut tobacco. Specifically, the compound is dissolved in ethanol, and the ethanol in which the compound is dissolved is uniformly sprayed on the tobacco, and then the ethanol is volatilized. The shredded tobacco is rolled into test sample cigarettes. The cigarettes of the same brand without adding this compound were used as the blank control group. After the cigarettes were balanced, cigarettes with similar average quality and average resistance were selected, and the electron spin resonance method was used to detect gas-phase free radicals. The average gas-phase free radical of the control cigarette is about 9.52 (spin number 10 14 / Pc), the average gas-phase free radicals of ...

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Abstract

The invention discloses a coumarin derivative and its preparation method and application. The coumarin derivatives of the present invention have a strong ability to resist oxidation, inhibit the formation of free radicals, and scavenge free radicals. When added to shredded cigarettes, they can inhibit and scavenge free radicals and reduce the effects of smoking on the human body. harm. The structural formula of the coumarin derivative is shown in formula (I): (I); the R1 is or, the R2, R3 and R4 are -H, -OH or -OCH3, and the R5 is -H or -OH.

Description

technical field [0001] The present invention relates to the technical field of compound synthesis and the technical field of tobacco, in particular to an antioxidant, more specifically to a coumarin derivative and its preparation method and application. Background technique [0002] As we all know, smoking is harmful to the human body. Smoking causes some terrible diseases such as bronchial and lung disease and cardiovascular disease, yet many people still smoke. [0003] It used to be believed that the toxicity of smoking comes from nicotine, but it is not the only toxic substance of smoking. The process of smoking is a complex combustion process. There are a large number of free radicals in the gaseous substances and tar produced by smoking, which can directly or indirectly attack human tissues and cause various diseases. [0004] Under normal conditions, the free radicals produced in the human body can be removed by itself, so the generation and removal of free radicals...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/56C07D405/14A24B15/40A24B15/36
CPCA24B15/403C07D311/56C07D405/14
Inventor 李峰胡静汪军霞
Owner CHINA TOBACCO GUANGDONG IND
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