Tyrosinase inhibitor based on natural product framework, preparation method of inhibitor and application of inhibitor
A technology of tyrosinase and natural products, which is applied in the preparation of organic compounds, carboxylate esters, skin care preparations, etc., can solve the problems of high price, poor activity, and inability to use in large quantities, and the method is easy to achieve , good application prospects, mild preparation conditions
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Embodiment 1
[0038] Synthesis of (E)-3-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)acrylic acid (intermediate A)
[0039]
[0040] At -5°C, tert-butyldimethylsilyl chloride (3.62g, 24.0mmol) was added to a solution of ferulic acid (3.88g, 20.0mmol) in dichloromethane (50mL), then triethylamine was added to react The pH of the solution was adjusted to 9-10. The reaction solution was stirred at room temperature for 5 hours. After the reaction was completed, the reaction solution was washed successively with 1N hydrochloric acid solution, saturated sodium bicarbonate solution and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure to obtain the intermediate as pale yellow oil. Then this intermediate was dissolved in MeOH / THF (6.0 mL, 1 / 2), and saturated sodium carbonate solution was added at room temperature and stirred for 2 hours. Then the solvent was removed, and the residue was diluted with dichloromethane, washe...
Embodiment 2
[0054] Synthesis of (E)-3-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)acrylic acid (intermediate A)
[0055]
[0056] At 10°C, tert-butyldimethylsilyl chloride (9.04g, 60.00mmol) was added to a solution of ferulic acid (3.88g, 20.00mmol) in dichloromethane (50mL), then pyridine was added to adjust the pH of the reaction solution to Adjust the value to 9~10. The reaction solution was stirred at room temperature for 15 hours. After the reaction was completed, the reaction solution was washed successively with 1N hydrochloric acid solution, saturated sodium bicarbonate solution and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure to obtain the intermediate as pale yellow oil. Then this intermediate was dissolved in MeOH / THF (6.0 mL, 1 / 2), and saturated potassium carbonate solution was added at room temperature and stirred for 6 hours. Then the solvent was removed, and the residue was diluted with dich...
Embodiment 3
[0070] Synthesis of (E)-3-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)acrylic acid (intermediate A)
[0071]
[0072]At 25°C, tert-butyldimethylsilyl chloride (15.07g, 100.0mmol) was added to a solution of ferulic acid (3.88g, 20.0mmol) in chloroform (50mL), and then N,N-diisopropyl Ethylamine adjusted the pH value of the reaction solution to 9-10. The reaction solution was stirred at room temperature for 24 hours. After the reaction was completed, the reaction solution was washed successively with 1N hydrochloric acid solution, saturated sodium bicarbonate solution and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure to obtain the intermediate as pale yellow oil. Then this intermediate was dissolved in MeOH / THF (6.0 mL, 1 / 2), and saturated sodium bicarbonate solution was added at room temperature and stirred for 10 hours. Then the solvent was removed, the residue was diluted with chloroform, and w...
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