Theanyl amino acid benzyl ester modified curcumin, its synthesis, activity and application
A technology of oxyacetyl theanyl and oxyacetyl benzyl ester group is applied in the field of biomedicine, and can solve the problems of unsatisfactory clinical efficacy of tumor chemotherapy, worsening prognosis of tumor patients, affecting the effect of chemotherapy and the like.
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Embodiment 1
[0018] Example 1 Preparation of 6-(4-hydroxy-3-methoxyphenyl)-5,6-hexene-2,4-dione (1)
[0019] Reflux 45.0 mL (437.7 mmol) of acetylacetone, 21.0 g (301.6 mmol) of boron oxide and 150.0 mL of anhydrous ethyl acetate at 60° C. for 1 h. Then, 22.5 g (148.0 mmol) of vanillin and 41 mL (293.0 mmol) of tributyl borate were added thereto. The reaction mixture was stirred at 70 °C for 30 min. Continue to add a solution of 15 mL (205.1 mmol) of n-butylamine and 135 mL of ethyl acetate within 30 min. The mixture was stirred at 100°C for 3 h, then cooled to room temperature, and 150 mL of hydrochloric acid (1M) was added dropwise thereto. The mixture was stirred at 50°C for 30 min, allowed to stand, and the layers were fully separated, and the aqueous layer was extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with saturated NaCl solution until neutral, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated to dryness under...
Embodiment 2
[0020] Example 2 Preparation of 3-methoxy-4-(oxyl-2-acetylbenzyl)benzaldehyde (2)
[0021] Dissolve 10 g (65.8 mmol) of vanillin in 100 mL of anhydrous tetrahydrofuran. To this solution was added portionwise 10.9 g (79.0 mmol) potassium carbonate and stirred for 3 h. Then, 9.3 mL benzyl bromoacetate was added dropwise to the solution, stirred at room temperature for 48 h, and TLC monitoring (petroleum ether / ethyl acetate=3 / 1) showed that the reaction was complete. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was washed with 100 mL of ether and allowed to stand for 12 h, then poured off the ether and washed with 10 mL of ether three times to obtain 15.4 g (78%) of the title compound as a colorless solid. ESI-MS(m / e): 301[M+H] + ; 1 H NMR (300MHz, DMSO-d 6 ):δ / ppm=9.86(s,1H),7.50(dd,J 1 =8.4Hz,J 2 =1.8Hz,1H),7.44(d,J=1.8Hz,1H),7.39(s,5H),7.11(d,J=8.4Hz,1H),5.21(s,2H),5.03(s,2H ), 3.84(s,3H).
Embodiment 3
[0022] Example 3 Preparation of 1-(4-hydroxy-3-methoxyphenyl)-7-(4-oxoacetylbenzyl-3-methoxyphenyl)-1,6-heptadiene-3, 5-diketone(3)
[0023] 5.55 g (23.7 mmol) of 6-(4-hydroxy-3-methoxyphenyl)-5,6-hexene-2,4-dione (1), 0.83 g (11.9 mmol) of boron oxide and 100 mL of acetic acid The ethyl ester suspension was refluxed at 70°C for 1h. After that, it was concentrated under reduced pressure. The residue was dissolved with 100 mL of anhydrous DMF. To the resulting solution were added 10.67 g (35.6 mmol) of 3-methoxy-4-(oxy-2-acetylbenzyl)benzaldehyde (2) and 11.15 mL (41.0 mmol) of tributyl borate. The resulting solution was stirred at 80 °C for 30 min. Afterwards, 0.98 mL (6.4 mmol) of n-butylamine was added dropwise in 4 times for 1 h, and the resulting solution was stirred at 80° C. for 3 h. After that, 200 mL of 10% aqueous acetic acid solution preheated to 60° C. was added thereto. The resulting solution was stirred for an additional 1 h at 80 °C. The reaction mixture w...
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