Rutin ester compound and application thereof in medicaments
A technology of ester compounds and compounds, applied in drug combinations, medical preparations containing active ingredients, sugar derivatives, etc.
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Embodiment 1
[0242] Example 1 (2R, 4S, 6R)-2-((5,7-diacetoxy-2-(3,4-diacetoxyphenyl)-4-oxo-4H-benzopyran- 3-yl)oxy)-6-((((2R,3R,4R)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy )methyl)tetrahydro-2H-pyran-3,4,5-triacetate
[0243]
[0244] synthetic route:
[0245]
[0246] In a dry 500mL round bottom flask, dissolve 30.5g of rutin in 200mL of pyridine, add 600mg of DMAP (4-dimethylaminopyridine), stir at room temperature for 10 minutes, slowly add 61.0g of Ac 2 O (acetic anhydride), continue to stir for 16 hours, evaporate most of the pyridine under reduced pressure, slowly pour the residue into cold water with vigorous stirring, and precipitate a yellow-white powder solid, filter, wash the solid and dry to obtain the target compound 50.5 g, the yield is 97.3%, and the HPLC purity is 95%.
[0247] MS(ESI,pos.ion)m / z:1053.1[M+Na];
[0248] 1 H-NMR (CDCl 3 )δ1.08(d,J=6.4Hz,3H),1.94(s,3H),1.96(s,3H),2.02(s,6H),2.09(s,3H),2.14(s,3H), 2.30(s,3H),2.33(s,3H),2.34(s,3H),2.43...
Embodiment 2
[0249] Example 2 (2R,4S,6R)-2-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-benzopyran-3-yl) Oxy)-6-((((2R,3R,4R)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl) Tetrahydro-2H-pyran-3,4,5-triacetate
[0250]
[0251] synthetic route:
[0252]
[0253] (2R,4S,6R)-2-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-benzopyran-3-yl)oxy )-6-((((2R,3R,4R)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro -2H-pyran-3,4,5-triacetate (20.6g) was dissolved in 100mL of methanol, 5.85g of imidazole was added, stirred at room temperature for 12 hours, the raw material disappeared, part of the methanol was evaporated, and adjusted to Weakly acidic, white turbidity appeared, extracted with dichloromethane, washed twice with saturated brine, dried over anhydrous sodium sulfate and evaporated to obtain the crude product, purified by column chromatography (eluent: petroleum ether: ethyl acetate = 2:3 ), the target compound was obtained as yellow-...
Embodiment 3
[0256] Example 3 (2R, 4S, 6R)-2-((5,7-dihydroxy-4-oxo-2-(2-thiobenzo[d][1,3]diox-5-yl) -4H-benzopyran-3-yl)oxy)-6-((((2R,3R,4R)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyridine Pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triacetate
[0257]
[0258] synthetic route:
[0259]
[0260] (2R,4S,6R)-2-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-benzopyran-3-yl)oxy )-6-((((2R,3R,4R)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro -2H-pyran-3,4,5-triacetate (3.445g) and 20mg 4-dimethylaminopyridine (DMAP) were placed in a dry one-necked bottle, the air was removed, N 2 Add 5 mL of redistilled acetonitrile under protection, stir and dissolve at 50°C, add 462 mg of thiocarbonyldiimidazole, continue stirring for 0.5 hours, distill off acetonitrile under reduced pressure, and purify on a silica gel column (eluent: petroleum ether: ethyl acetate = 4 :5), to obtain 2.24g of yellow-white powder, namely the title compound, with a yield of 60.8% and a...
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