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
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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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