Schiff base and preparation method thereof as well as application serving as cigarette free-radical scavenger
A Schiff base and free radical technology, applied in the field of compound synthesis and preparation, can solve problems such as tissue damage and oxygen stress, and achieve strong anti-oxidation, harm reduction, and suppression of harmful substances in cigarettes
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Embodiment 1
[0039] Example 1 Synthesis of Schiff's Base
[0040] The synthetic route design is as follows:
[0041]
[0042] The preparation steps are as follows:
[0043] S1. First add anhydrous methanol as a solvent in a 100mL Erlenmeyer flask, then add diamine reactants and hydroxyaldehydes in a molar ratio of 1:2, stir at room temperature for 3 to 4 hours, and use TLC (thin-layer chromatography method) ) to track the progress of the reaction;
[0044] S2.S1 When the reaction is complete, solids are precipitated, left to stand, filtered with suction to obtain solids, washed with anhydrous methanol for 3 times, and dried by infrared to obtain the product.
[0045] The structural formula of the prepared compound is as follows:
[0046]
[0047]
[0048]
[0049]
[0050] The structures of the synthesized compounds are characterized as follows:
[0051] Compound 1: 1 H NMR (300 MHz, DMSO- d 6 ): 8.09 (s, 2H), 7.17 (s, 2H), 6.94 (d, J = 8.1 Hz, Hz, 2H), 6.73 (d, J...
Embodiment 2
[0071] Example 2 Activity experiment of inhibiting and scavenging free radicals
[0072] 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, Biochemistry and Biophysics Progress, 1996,23 (6): 553-555] introduced the method and made appropriate improvements, using the Fenton reaction to complete the determination.
[0073] 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.
[0074] Calculation method: free radical scavenging rate EC 50 =(A s -A 0 ) / (A 1 -A 0 )
[0075] Among them, As is the addition of the sample to be tested and H 2 o 2...
Embodiment 3
[0080] Example 3 Experiments using cigarettes
[0081] 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 0.012% 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 numbe...
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