Icariin derivatives
A technology of icariin and derivatives is applied in the directions of sugar derivatives, sugar derivatives, sugar derivatives preparation, etc., to achieve the effect of excellent medicinal effect.
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Embodiment 1
[0035] Example 1 Preparation of Icariin Derivatives (Compounds 7, 8) of the present invention
[0036] Dissolve 5 g (7.4 mmol, 1 equiv) of ICA in 30 mL of DMF, add 5.7 g (51.8 mmol, 7 equiv) of triethylamine in an ice bath, stir for 10 min, add 5.7 g (51.8 mmol, 7 equiv) of acetic anhydride dropwise, and Stirred in the bath for 6h, quenched with ice water, filtered, washed with water, dissolved in ethyl acetate, dried over anhydrous MgSO4, concentrated in vacuo, and column chromatographed to obtain an alcoholic hydroxyl-protected icariin derivative (1 g, 15%). Dissolve 0.5 g (0.52 mmol, 1 equiv) of the protected product in 2 mL of anhydrous acetone, add appropriate amount of anhydrous K2CO3, catalytic amount of KI, stir for 10 min, add 0.55 mmol (1.1 equiv) of 1,3-dibromopropane or Ethyl bromoacetate, stirred at room temperature for 1-3h, and monitored the reaction by TLC. After the reaction was completed, the solid was removed by filtration, and the filtrate was concentrated ...
Embodiment 2
[0039] Example 2 Synthesis of Nitrogenous Derivatives of Icariin (Compounds 9 and 10)
[0040] Take 0.19g (0.17mmol, 1equiv) of compound 7 and dissolve it in anhydrous acetone, add an appropriate amount of K 2 CO 3 and catalytic amount KI, stirred at room temperature for 10 min, added piperidine or piperazine, stirred at room temperature for 30 min, filtered to remove solids, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography to obtain products 9 and 10.
[0041]Compound 9: Yellow powder, yield 90%.Mp.120~121℃; 1H NMR (400MHz, CDCl3) δ7.82(d, 2H, J=8.80Hz), 7.06(d, 2H, J=8.80Hz) ,6.92(s,1H),5.67(t,1H,J=2.08Hz),5.52(d,1H,J=7.04Hz),5.45(s,1H),5.32~5.40(m,2H),5.23~ 5.03(m, 2H), 5.06(t, 1H, J=6.56Hz), 4.96(t, 1H, J=10.08Hz), 4.64(bs, 1H), 4.39~4.31(m, 4H), 3.90(s ,3H),3.71~3.77(bs,4H),3.38~3.48(m,2H),2.50(d,2H,J=5.12Hz),2.13(s,3H),2.03(s,3H),2.00( d, 6H, J=3.84Hz), 1.68(s, 3H), 1.66(s, 3H), 1.63(s, 15H), 1.22~1.26(m, 3H), 0.81(d...
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