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Preparation method of 5,6,7,4'-tetramethoxy flavones of scutellarin and aglucone key intermediate thereof

A technology of tetramethoxyflavone and scutellarin, which is applied in the field of compound preparation, can solve problems such as complicated operation requirements, and achieve the effects of simple operation steps, good application value and high product yield

Inactive Publication Date: 2010-03-31
KPC PHARM INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method is operated through three steps of reaction, and the yield of each step reaction is also good, but the operation requirements are more cumbersome

Method used

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  • Preparation method of 5,6,7,4'-tetramethoxy flavones of scutellarin and aglucone key intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: the preparation of chalcone (compound 3)

[0018] Weigh 11.3g (0.05mol) of the compound 2,2-hydroxy-4,5,6-trimethoxyacetophenone and 7.4g (0.06mol) of p-methoxybenzaldehyde in a 250ml round bottom flask, add 150ml of methanol and 22.5 g of solid KOH, stirred and reacted at room temperature for 36 hours. After most of the methanol was distilled off under reduced pressure, 200ml of water was added, and then the pH was adjusted to 3-4 with concentrated hydrochloric acid. Precipitate a red precipitate, put it well and filter it, wash the precipitate with a little water, press dry, and dry at 60°C. Example 1 is the first step reaction of the present invention to prepare scutellarin and its aglycone key intermediate 5,6,7,4'-tetramethoxyflavone, which is obtained from 2-hydroxy-4,5,6- The chalcone derivative (compound 3) was prepared by condensation of trimethoxyacetophenone and p-methoxybenzaldehyde. The first step was reacted to obtain 14.5 g of compound 3 a...

Embodiment 2

[0019] Embodiment 2: the preparation of 5,6,7,4'-tetramethoxyflavone (compound 1)

[0020] Weigh 17.2g (0.05mol) of compound A9 into a 250ml round bottom flask, add 50ml of DMSO and a little iodine, heat to reflux for 30min, then let the reaction solution cool down, add 100ml of cold water, stir well, and filter to obtain the compound A7 is off-white crystal. Example 2 is the second step reaction of the present invention to prepare scutellarin and its aglycone key intermediate 5,6,7,4'-tetramethoxyflavone, which is derived from the chalcone prepared in Example 1 5,6,7,4'-tetramethoxyflavone was obtained after oxidative cyclization of compound (compound 3). In the second step, 14.6 g of dry product of compound 1 was obtained, and the reaction yield was about 85%. 1 HNMR (CDCl 3 ): δ7.83(d, J=9.0Hz, 2H), δ7.01(d, J=9.0Hz, 2H), δ6.81(s, 1H), δ6.59(s, 1H), δ4. 00(s, 3H), δ3.99(s, 3H), δ3.93(s, 3H), δ3.89(s, 3H). MS (m / e): 342.

[0021] The above two examples illustrate the tw...

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Abstract

The invention relates to a preparation method of 5,6,7,4'-tetramethoxy flavone of scutellarin and aglucone key intermediate thereof. The 5,6,7,4'-tetramethoxy flavones is prepared by utilizing 2-hydroxyl-4,5,6-trimethoxy hypnone as the raw material and comprising a reaction a step and a reaction b step, wherein in the reaction a, 2-hydroxyl-4,5,6-trimethoxy hypnone and p-methoxybenzaldehyde are condensed to prepare a chalcone derivative; and in the reaction b, the chalcone derivative is processed in a oxidative cyclization mode to prepare the 5,6,7,4'-tetramethoxy flavone. The method has the advantages of simple operation steps and high product yield.

Description

technical field [0001] The invention relates to a compound preparation process, in particular to a preparation method of scutellarin and its aglycone key intermediate 5,6,7,4'-tetramethoxyflavone. Background technique [0002] Erigeron breviscapus, also known as Erigeron breviscapus, belongs to the genus Fabaceae. The scutellarin is isolated and extracted from the whole plant of breviscapine, mainly containing scutellarin (>90%), and also contains a small amount of scutellarin, which is also called scutellarin. Breviscapine has the effects of promoting blood circulation and removing blood stasis, dispelling cold and relieving the surface, relaxing tendons and activating collaterals, expelling wind and dampness, and is often used clinically to treat cardiovascular and cerebrovascular diseases. [0003] 5,6,7,4'-tetramethoxyflavone is an important intermediate for the preparation of cardiovascular drugs scutellarin and scutellarin aglycone (Cui Jianmei et al., "Natural Pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
Inventor 杨健杨兆祥杨波普俊学徐树光
Owner KPC PHARM INC
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