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A kind of coumarin derivative and its preparation method and application

A technology for coumarin derivatives and cigarettes, which is applied in the field of coumarin derivatives and its preparation, can solve problems such as tissue damage and oxygen stress, and achieve strong anti-oxidation, inhibit free radical scavenging, and mild preparation conditions Effect

Active Publication Date: 2016-09-07
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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  • A kind of coumarin derivative and its preparation method and application
  • A kind of coumarin derivative and its preparation method and application
  • A kind of coumarin derivative and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0039] The synthesis of embodiment 1 compound

[0040] Chemicals of the present invention can be synthesized by any of the following methods:

[0041] (1) Method 1:

[0042]

[0043] The specific preparation steps are as follows: first add absolute ethanol as a solvent in a 100mL Erlenmeyer flask, then add coumarin reactants and hydroxyaldehydes in a molar ratio of 1:1, stir for 3 to 4 hours under reflux, and then test with TLC (thin layer chromatography method) to track the reaction process, when the reaction is complete, solids are precipitated. Let stand for 1 hour, filter with suction, wash the solid three times with anhydrous methanol, and dry by infrared to obtain the product.

[0044] or (2) Method 2:

[0045]

[0046] Concrete preparation steps are:

[0047] In a 100mL conical flask, first add 30mL of anhydrous methanol as a solvent, then add coumarin compounds and hydroxyaldehydes in a molar ratio of 1:1, stir at room temperature for 12 hours, and track the ...

Embodiment 2

[0055] Example 2 Research experiments on the activity of inhibiting and scavenging free radicals

[0056] References [Jin Ming, Cai Yaxin, et al. O-phenanthroline-Fe 2+ Oxidation method to detect H 2 o 2 , Fe 2+ Hydroxyl free radicals produced, Progress in Biochemistry and Biophysics, 1996, 23 (6): 553-555] introduced the method, using the Fenton reaction to complete the determination.

[0057] Operation steps: In a 10mL volumetric flask, add 1.5mL of 5mmol / L o-phenanthroline, the pH is 7.4, 3mL of 0.5mol / L phosphate buffer, 7.5mmol / L of FeSO 4 1.0mL, mix immediately. Then add 3 mL of the sample to be tested, 0.1% H 2 o 2 1.0mL, dilute to 10mL with distilled water. After mixing, heat in a water bath at 37°C for 1 hour, and then measure its absorbance at a wavelength of 510nm.

[0058] Calculation method: free radical scavenging rate EC 50 =(A s -A 0 ) / (A 1 -A 0 )

[0059] Among them, A s In order to add the sample to be tested and H 2 o 2 The absorbance val...

Embodiment 3

[0063] Example 3 Experiments using cigarettes

[0064] Choose a certain brand of cigarette leaves and divide them into two groups, and add the compound of the present invention into shredded tobacco respectively during the shredded tobacco rolling process. The amount of the compound added accounts for 0.01% of the total mass of the shredded tobacco. Specifically, the compound is dissolved in ethanol, and the ethanol in which the compound is dissolved is evenly sprayed on the shredded tobacco, and the ethanol volatilizes subsequently. The shredded tobacco is rolled to make test sample cigarettes. 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 weight and average draw resistance were selected, and gas phase free radicals were detected by electron spin resonance method. The average gas phase free radicals of the control group cigarettes was about 9.52 (spin number...

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Abstract

The invention discloses a coumarin derivative and a preparation method and application thereof. The coumarin derivative has strong antioxidant ability, free radical formation inhibiting ability and free radical scavenging ability, can suppress and scavenge free radicals by adding of the coumarin derivative into cigarette tobacco, and can reduce the harm brought to human body by smoking. The structural formula of the coumarin derivative is shown as a formula (I);R is -OH or -H, R1 is a group shown as formula (a) or formula (b) or formula (c) (shown in the specification), R2, R3 and R4 are -H, -OH or -OCH3.

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): C07D311/56C07D405/06A24B15/40
CPCA24B15/403C07D311/56C07D405/06
Inventor 李峰胡静汪军霞韩冰
Owner CHINA TOBACCO GUANGDONG IND
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