Method for preparing dewatered icaritin through total-synthesis

A dehydrated icariin, total synthesis technology, applied in the production of bulk chemicals, organic chemistry and other directions, can solve the problems of many side compounds, expensive catalysts, complicated processes, etc., and achieves simple operation, low reaction equipment requirements, and reasonable methods. Effect

Active Publication Date: 2019-05-21
北京东方百奥医药开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Purpose of the invention: the technical problem to be solved by this invention is to overcome the low yield of introducing isopentenyl in the prior art, complex process, expensive catalyst and many by-compounds. The base is connected to the 8-position through the rearrangement of the ortho position, and then a series of reactions are carried out to form the flavone skeleton, the yield is improved, the use of microwaves is avoided, and a method is provided that is simple, the process is stable, and it is suitable for the preparation of industrialized production. The method of sheepskin

Method used

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  • Method for preparing dewatered icaritin through total-synthesis
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  • Method for preparing dewatered icaritin through total-synthesis

Examples

Experimental program
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Effect test

Embodiment 1

[0076] A kind of method of fully synthetically preparing dehydrated icariin, such as figure 2 Shown synthetic route, comprises the following steps:

[0077] 1. hydroxyl protection

[0078] Dissolve trihydroxyacetophenone (16.8g, 0.1mol) in acetone (500ml), add anhydrous potassium carbonate (13.8g, 0.1mol), heat up to 50°C and reflux; take dimethyl sulfate (25.2g, 0.2 mol), add one-third to the reaction solution every 3 hours, put it under reflux at 50°C for 9 hours, filter the reaction solution, evaporate the filtrate to dryness, and obtain a yellow solid, which is washed with water three times and then dried at low temperature to obtain off-white Solid product I (14.8g), yield 76%

[0079] 2. Introduce the B ring

[0080] Dissolve the product I (19.6g, 0.1mol) in anhydrous tetrahydrofuran (500ml), add 1 times the amount of NaH (2.4g, 0.1mol) after cooling down to 0°C, add 1.2 times the amount of p-methoxybenzene after stirring for 5min Formyl chloride (20.5g, 0.12mol), ...

Embodiment 2

[0106] A kind of method of fully synthetically preparing dehydrated icariin, such as figure 2 Shown synthetic route, comprises the following steps:

[0107] 1. hydroxyl protection

[0108] Dissolve trihydroxyacetophenone (16.8g, 0.1mol) in 500ml of acetone, add anhydrous potassium carbonate (41.4g, 0.3mol), heat up to 60°C and reflux; take dimethyl sulfate (25.2g, 0.2mol) , add one-third to the reaction solution every 3 hours, put it under reflux at 50°C for 9 hours, then filter the reaction solution, evaporate the filtrate to dryness to obtain a yellow solid, wash it with water three times and dry it at low temperature to obtain an off-white solid product I (15.3 g), yield 79%.

[0109] 2. Introduce the B ring

[0110] Dissolve the product I (19.6g, 0.1mol) in anhydrous tetrahydrofuran (500ml), add 2 times the amount of NaH (4.8g, 0.2mol) after cooling down to 0°C, add 1.2 times the amount of p-methoxybenzene after stirring for 5min Formyl chloride (20.5g, 0.12mol), the...

Embodiment 3

[0136] A kind of method of fully synthetically preparing dehydrated icariin, such as figure 2 Shown synthetic route, comprises the following steps:

[0137] 1. hydroxyl protection

[0138] Dissolve trihydroxyacetophenone (16.8g, 0.1mol) in 500ml of acetone, add anhydrous potassium carbonate (27.6g, 0.2mol), heat up to 56°C and reflux; take dimethyl sulfate (25.2g, 0.2mol) , add one-third to the reaction solution every 3 hours, put it under reflux at 56°C for 9 hours, filter the reaction solution, evaporate the filtrate to dryness, and obtain a yellow solid, wash it with water three times, and dry it at low temperature to obtain an off-white solid product I (16.3g), 83% yield.

[0139] 2. Introduce the B ring

[0140] Dissolve the product I (19.6g, 0.1mol) in anhydrous tetrahydrofuran (500ml), add 1.5 times the amount of NaH (3.6g, 0.15mol) after cooling down to 0°C, add 1.2 times the amount of p-methoxybenzene after stirring for 5min Formyl chloride (20.5g, 0.12mol), the...

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Abstract

The invention provides a method for preparing dewatered icaritin through total-synthesis. The method includes the steps of connecting an isopentene group to 8th-position carbon through ortho-positionrearrangement with methoxybenzoyl chloride, isoprenyl bromide and the like as the raw materials by means of trihydroxyacetophenone, and conducting the forming series reaction of a flavone framework toobtain the dewatered icaritin. The defects that in a traditional method of introducing an isopentene group, the yield is low, catalysts are expensive and lots of byproducts are produced are overcome,and the method is low in cost, simple in operation, good in yield and suitable for industrial production.

Description

technical field [0001] The invention relates to drug synthesis, in particular to a method for fully synthesizing dehydrated icariin. Background technique [0002] Dehydrated icariin has the following formula: [0003] [0004] Flavonols are ubiquitous in plants and have attracted much attention because of their extensive and effective biological activities. As an important member, icariin has biological activities such as anti-tumor, anti-cancer cell proliferation, anti-osteoporosis, regulation of estrogen, and regulation of the nervous system. Although icariin can be obtained by hydrolyzing icariin, the content of icariin in nature is low, and its separation and purification are complicated. Therefore, obtaining icariin in a synthetic way is the preferred strategy for drug research and industrial production, in which the construction of flavonol skeleton and the introduction of isopentenyl are the key points. There are three main methods to achieve the former: (1) cla...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04
CPCY02P20/55
Inventor 刘接卿马俊杰连晨蕾肖琴辛钟成辛华顾静良姚正
Owner 北京东方百奥医药开发有限公司
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