Colacea-4-O-acetyl-Gly-Asp-Val salt, its synthesis, activity and application
A curcumin, -val-obzl technology, applied in the field of biomedicine, can solve the problems of strontium ranelate with large side effects, large clinical dosage, and poor solubility
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Embodiment 1
[0016] Example 1 Preparation of 3-methoxy-4-(benzyl acetateoxy)benzaldehyde (1)
[0017] Dissolve 15.2 g (100 mmol) of vanillin in 100 mL of anhydrous tetrahydrofuran, add 6.9 g (50 mmol) of anhydrous potassium carbonate, stir at room temperature for 2 h, after the solution changes from pale yellow to milky white turbid state, add 15 mL (76 mmol) of benzyl bromoacetate Ester, stirred at 60 ° C for 48 h. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the residue was dissolved in 100 mL of ethyl acetate. The resulting solution was prepared with 5% KHSO 4 Washed with aqueous solution (30mL×3) and saturated NaCl aqueous solution (30mL×3), washed with anhydrous Na 2 SO 4 Dry for 12 h, filter, and concentrate the filtrate under reduced pressure. The residue is placed in anhydrous ether to precipitate 27.6 g (92%) of the title compound as colorless crystals. ESI-MS(m / e):301[M+H] + .
Embodiment 2
[0018] Example 2 Preparation of 6-(4-hydroxy-3-methoxyphenyl)-5,6-hexene-2,4-dione (2)
[0019] Disperse 9.9 mL (97.0 mmol) of acetylacetone in 50 mL of anhydrous ethyl acetate, add 4.6 g (66.7 mmol) of boron anhydride, and stir at 60 °C for 1 h. After that, 5.06 g (33.3 mmol) of vanillin and 9 mL (33.5 mmol) of tri-n-butyl borate were added successively, and the mixture was stirred at 80° C. for 0.5 h. After that, add 34 mL of n-butylamine in anhydrous ethyl acetate solution (1 / 10, v / v), and stir at 80 °C for 2 h. Cool to 60 ℃, add 34 mL of dilute hydrochloric acid (1 M), stir for 0.5 h, and cool to room temperature. Filter, filtrate with 5% KHSO 4 Washed with aqueous solution (30mL×3) and saturated NaCl aqueous solution (30mL×3), washed with anhydrous Na 2 SO 4 It was dried for 12 h, filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 3.1 g (40%) of the title compound as a pale yellow ...
Embodiment 3
[0020] Example 3 Preparation of 1-(4-hydroxy-3-methoxyphenyl)-7-(4-oxyacetylbenzyl ester-3-methoxyphenyl)-1,6-heptadiene-3, 5-Dione (3)
[0021] 5 g (21.4 mmol) of 6-(4-hydroxy-3-methoxyphenyl)-5,6-hexene-2,4-dione (2), 3 g (42.8 mmol) of boronic anhydride and 30 mL of Water and ethyl acetate suspension. The suspension was stirred at 60 °C for 1 h, 6.4 g (21.4 mmol) of 3-methoxy-4-(benzyl acetateoxy)benzaldehyde and 5.7 mL (21.2 mmol) of tri-n-butyl borate were added, and the mixture was stirred at 80 °C for 0.5 h , Add 21 mL of n-butylamine in anhydrous ethyl acetate (1 / 10, v / v), and stir for 2h. Cool to 60 ℃, add 42.7 mL of dilute hydrochloric acid (1 M), stir for 0.5 h, and cool to room temperature. Filter, filtrate with 5% KHSO 4 Washed with aqueous solution (30mL×3) and saturated NaCl aqueous solution (30mL×3), washed with anhydrous Na 2 SO 4 It was dried for 12 h, filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica...
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