3-glyeosyl flavone or its derivative and its preparation method and use

A technology of glycosyl flavonoids and derivatives, which is applied in the field of flavonoids and can solve problems such as difficult handling, many reaction steps, and long reaction time

Inactive Publication Date: 2004-03-03
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] There are certain limitations in the above three methods. Method one is difficult to deal with after the reaction due to the high concentration of silver salt in the system; the reaction time of method two is long; the reaction steps of method three are many

Method used

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  • 3-glyeosyl flavone or its derivative and its preparation method and use

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Example 1: Synthesis of 3-(2,3,4-triacetyl-L-rhamnopyranosyl)flavone:

[0031] 3-Hydroxyflavone (2.751 g, 0.0116 mol) and 2,3,4-triacetyl-1-oxo-α-L-rhamnopyranosyl trichloroethylimine (5.022 g, 0.0116 mol) were mixed , after vacuum drying for 2 h, 180 ml of anhydrous CH was added to the mixture 2 Cl 2 , the system was cooled to -42°C in a liquid nitrogen-ethanol bath, N 2 Trimethylsilyl trifluoromethanesulfonate (TMSOTf)-247 μl was added dropwise under protection. After the addition was completed, the reaction system was removed from the cooling bath, and the reaction system gradually returned to room temperature. Ethyl acetate=3:2) After monitoring the reaction, triethylamine was added to the system to terminate the reaction, and the solvent was removed by a rotary evaporator to obtain a brown-yellow viscous liquid, which was separated and purified by chromatography on a silica gel column (eluent For: petroleum ether: ethyl acetate = 3: 1)) to obtain 1.215 g of whit...

Embodiment 2

[0040] The synthesis of embodiment 2.3-L-rhamnopyranosyl flavone:

[0041] Add 3-(2,3,4-triacetyl-L-rhamnopyranosyl)flavone (0.601 g, 1.178 mmol) to CH 3 After OH25ml was dissolved, NH 3To saturation, the time is about 4h. After standing at room temperature for 48h, thin-layer chromatography (developing solvent: petroleum ether: ethyl acetate = 1:5) monitors that there is no raw material in the system, and the solvent is removed by a rotary evaporator to obtain an orange-yellow solid. Separation and purification by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:5) gave 0.385 g of white solid, mp.96-99°C, yield 83.6%. Compound by 1 H-NMR, 13 C-NMR, IR, MS and elemental analysis for structural verification, the results show that its structure is correct, the data are as follows:

[0042] 1 H-NMR (300MHz, DMSO-D6):

[0043] 8.12 (d, 1H J = 7.71Hz) 7.91 (m, 2H) 7.83 (t, 1H, J = 8.20, 7.22Hz) 7.77 (d, 1H, J = 8.20Hz) 7.58 (m, 3H) 7.51 (t, 1H, J=...

Embodiment 3

[0051] Synthesis of Example 3.3-(2,3,4,6-tetraacetyl-D-glucopyranosyl)flavone (VI):

[0052] 3-Hydroxyflavone (1.088g, 4.57mmol) was mixed with 2,3,4,6-tetraacetyl-1-oxo-α-D-glucopyranosyltrichloroethylimine (2.251g, 4.57mmol) , after vacuum drying for 2 h, 150 ml of anhydrous CH was added to the mixture 2 Cl 2 , the system was cooled to -78°C in a liquid nitrogen-ethanol bath, N 2 98 μl of trimethylsilyl trifluoromethanesulfonate (TMSOTf) was added dropwise under protection. After the addition was completed, the reaction system was removed from the cooling bath, and the reaction system gradually returned to room temperature. Ethyl ester = 3: 2) After monitoring the reaction, triethylamine was added to the system to terminate the reaction, and the solvent was removed by a rotary evaporator to obtain a brownish-yellow viscous solid, which was separated and purified by chromatography on a silica gel column (the eluent was Petroleum ether:ethyl acetate=3:1) to obtain 1.25g of ...

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Abstract

A 3-glycosylflavone or its derivatives, their preparing process, and their application in preparing the medicines for treating immune diseases, such as autoimmunity disease or allergic disease, are disclosed.

Description

1. Technical field [0001] The present invention relates to flavones, in particular to 3-glycosylflavones. 2. Background technology [0002] Flavonoid glycosides are a class of natural organic compounds that widely exist in nature, they have a series of important physiological activities, for example: 3-glycosyl flavonoid glycosides can be used to treat various cardiovascular diseases, and can also be used as immune suppression agent. 3,7,3',4'-tetrahydroxy-3-L-rhamnopyranosylflavanone (Astilbin) and its analogs 5,7,3',5'-tetrahydroxy-3-L- 3-glycosyl flavonoid glycosides such as rhamnopyranosyl flavanone (Smitilibin), 5,7-dihydroxy-3-L rhamnopyranosyl chromone (Eucryphin) on the whole disease model or cell model It shows selective immunosuppressive effect, and has no common toxic and side effects of existing drugs. [0003] However, since there are few effective methods for the synthesis of flavonoid glycosides, most flavonoid glycosides mainly rely on natural extraction...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/7048A61P37/02A61P37/08C07H17/07
Inventor 郭子建杨晓亮徐强张先明涂超张子超
Owner NANJING UNIV
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