Preparation method of acryloyl chloride esterified traditional Chinese medicine monomer pterostilbene

The technology of acryloyl chloride ester and acryloyl chloride is applied in the field of preparation of acryloyl chloride esterified traditional Chinese medicine monomer pterostilbene, which can solve the problems of poor water solubility and low bioavailability, and achieves mild conditions, simple preparation method and scientific and reasonable structure. Effect

Inactive Publication Date: 2021-08-31
YUNNAN UNIV OF TRADITIONAL CHINESE MEDICINE
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Problems solved by technology

It is found that many traditional Chinese medicine monomers have shown good effects in improving the body's antioxidant capacity and reducing inflammation, pterostilbene (Pterostilbene, PTE), 3,5-dimethoxy-4'-hydroxystilbene, As a trans-stilbene compound, it is a methylated derivative of resveratrol, and its bioavailability is higher and more stable than that of resveratrol. Various biological activities such as tumors, and various preventive and therapeutic effects on neurological diseases, cardiovascular diseases, metabolic diseases and blood diseases, but most pterostilbene traditional Chinese medicine monomers have problems such as poor water solubility, which leads to their failure to maximize Limit the biological activity, and according to the pharmacokinetic study of pterostilbene, the oral bioavailability of pterostilbene is low, which may be due to the first-pass effect reduces the drug content in the blood, and the application of traditional Chinese medicine monomers in the field of biomaterials is relatively seldom Therefore, research on the development of traditional Chinese medicine monomers from the field of biomaterials is of high value. Due to the superior performance and chemical properties of polymer materials, research on its modification and application has become more and more in-depth, especially biomedical polymer materials. It has the advantages of stable mechanical properties, good chemical inertness, stable physical properties, good biocompatibility, economical materials, suitable for civilian consumption, and easy access to materials. It has been widely used and has extremely broad development value.

Method used

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  • Preparation method of acryloyl chloride esterified traditional Chinese medicine monomer pterostilbene
  • Preparation method of acryloyl chloride esterified traditional Chinese medicine monomer pterostilbene
  • Preparation method of acryloyl chloride esterified traditional Chinese medicine monomer pterostilbene

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preparation example Construction

[0031] The preparation method of acryloyl chloride esterified traditional Chinese medicine pterostilbene comprises the following steps:

[0032] Step 1, measuring a certain proportion of tetrahydrofuran and pyridine as a mixed solvent and adding it to a four-necked flask with a stirrer, a reflux condenser and a thermometer;

[0033] Step 2, adding an appropriate amount of pterostilbene into the four-necked flask for stirring, and simultaneously adding acryloyl chloride dropwise to the four-necked flask with a dropping funnel at a moderate speed;

[0034] Step 3, after the dropwise addition, start the heating reaction. After the reaction, pour the obtained liquid into a large amount of water, neutralize with hydrochloric acid, wash and dry repeatedly, and then obtain Acrylicaid-PTE, and finally High-purity Acrylic acid-PTE product can be obtained after being separated by a separation column.

[0035] In the present invention, preferably, in step 1, the mass ratio of tetrahydro...

Embodiment 1

[0055] (1) Measure a certain proportion of tetrahydrofuran and pyridine as a mixed solvent and add it to the flask, add an equivalent amount of pterostilbene for stirring, and add acryloyl chloride dropwise at a moderate speed. Heating, after the reaction is over, the obtained liquid is poured into a large amount of water, neutralized with hydrochloric acid, washed repeatedly, and dried to obtain acrylated pterostilbene (Acrylicaid-PTE), such as figure 1 shown. Pterostilbene is endowed with a C=C double bond.

[0056] (2) Under the condition of reaction temperature 80℃, pterostilbene:acryloyl chloride=1:3, the effect of reaction time on the yield was investigated. As shown in Table 1. Its yield is about more than 80%, and the yield of Acrylicaid-PTE increases with the increase of the reaction time; When the reaction time is 8h, the Acrylicaid-PTE yield is 82.5%, namely maximum yield; Continue to increase the reaction time, yield rate did not increase significantly. The max...

Embodiment 2

[0060] (1) First, synthesize the macromolecular initiator pAAPBA (such as figure 2 shown). Using AAPBA as a monomer, AIBN as an initiator, and DMF as a solvent, the resulting solution was transferred to a sealed reaction bottle, and reacted in a preheated oil bath at 70°C in nitrogen for 12 hours. After cooling in ice water for 5 min, the resulting polymer was poured into 1 ml of methanol, the precipitate was washed with ether, filtered, and vacuum-dried to obtain p(AAPBA) polymer.

[0061] (2) Next, a certain amount of pAAPBA and Acrylicaid-PTE were used as reactive monomers, AIBN was used as an initiator, DMF and water were added to mix, and sealed in a 50ml round bottom flask. Then use a vacuum pump to evacuate air and nitrogen until the bubbles disappear, then fill the flask with enough nitrogen, repeat three cycles, and place the flask in an oil bath for 12 hours (temperature 70 ° C, rotation speed 7). Finally, the reaction flask was placed in ice water to stop the pol...

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Abstract

The invention discloses a preparation method of an acryloyl chloride esterified traditional Chinese medicine monomer pterostilbene. Adopted components comprise a traditional Chinese medicine monomer pterostilbene and acryloyl chloride. The preparation method comprises the following steps: putting a mixed solvent of tetrahydrofuran and pyridine into a flask, adding the pterostilbene, stirring, dropwise adding the acryloyl chloride at a moderate speed, heating, pouring into a large amount of water after the reaction is finished, neutralizing with hydrochloric acid, repeatedly cleaning and drying to obtain acrylic acid esterified pterostilbene, and finally separating the acrylic acid esterified pterostilbene with a separation column to obtain a high-purity PTE product so as to endow the pterostilbene with a C=C double bond. The prepared esterified pterostilbene can be combined with a high polymer material (such as phenylboronic acid) to prepare a medicinal sustained-release auxiliary material (such as nano particles). In the in-vivo degradation process, the pharmacological action of the traditional Chinese medicine monomer pterostilbene is fully played, the effective in-vivo drug concentration can be maintained for a long time, the toxic and side effects of a biological material are reduced, and a patient is most effectively treated.

Description

technical field [0001] The invention belongs to the technical field of preparation of polymer slow-release auxiliary materials, and in particular relates to a preparation method of pterostilbene, a traditional Chinese medicine monomer, which is esterified with acryloyl chloride. Background technique [0002] With the continuous exploration of the development and application of traditional Chinese medicine, the monomer of traditional Chinese medicine has gradually attracted everyone's attention. It is found that many traditional Chinese medicine monomers have shown good effects in improving the body's antioxidant capacity and reducing inflammation, pterostilbene (Pterostilbene, PTE), 3,5-dimethoxy-4'-hydroxystilbene, As a trans-stilbene compound, it is a methylated derivative of resveratrol, and its bioavailability is higher and more stable than that of resveratrol. Various biological activities such as tumors, and various preventive and therapeutic effects on neurological d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/14C07C69/54A61K47/58A61K31/222A61K31/09A61P3/10
CPCA61K31/09A61K31/222A61K47/58A61P3/10C07C67/14C07C69/54
Inventor 武俊紫石安华陈文慧马琼赵茜
Owner YUNNAN UNIV OF TRADITIONAL CHINESE MEDICINE
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