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Synthetic method of puerarin derivatives

A technology of puerarin derivatives and synthesis methods, which is applied in the direction of sugar derivatives, drug combinations, cardiovascular system diseases, etc., can solve the problems of reducing biological activity, etc., and achieve the effects of simple operation, high yield, and easy industrial application

Inactive Publication Date: 2009-12-02
LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen from the above that the structural modification of puerarin is currently mainly concentrated on the phenolic hydroxyl group and sugar C-6″alcohol hydroxyl group, but the main functional group of puerarin-phenolic hydroxyl group is combined or shielded during the reaction process, thereby reducing the biological activity of the substance itself

Method used

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Experimental program
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Effect test

Embodiment 13

[0019] The synthesis of embodiment 13'-methylene-dimethylamine-puerarin

[0020] Dimethylamine hydrochloride first undergoes Mannich reaction with formaldehyde to generate methylene-diimine, and then methylene-diimine undergoes condensation reaction with puerarin phenolic hydroxyl group ortho to generate 3′-methylene-dimethylamine-pueraria white.

[0021] (1) Preparation of dimethylamine aqueous solution

[0022] Accurately weigh 30g dimethylamine hydrochloride (CH 3 )2NH.HCL, and then add a certain amount of distilled water to prepare a 50-70% aqueous solution;

[0023] (2) Synthesis of two-(dimethylamino)methane

[0024] Under cooling in an ice bath, add 5-25ml of 37%-40% formaldehyde aqueous solution to a 100mL three-neck round-bottomed flask, and while stirring, add 0.25-0.45mol of dimethylamine aqueous solution (add dropwise with a dropping funnel, Keep the reaction temperature lower than 50°C), dropwise is completed, stir at room temperature for 15-45 minutes, then a...

Embodiment 23

[0033] Embodiment 23', the synthesis of 5'-methylene-diethylamine-puerarin

[0034] Diethylamine first undergoes Mannich reaction with formaldehyde to generate methylene-diethylamine, and then methylene-diethylamine undergoes condensation reaction with puerarin phenolic hydroxyl group ortho to generate 3′, 5′-methylene-diethylamine - Puerarin.

[0035] (1) Synthesis of two-(diethylamine) methane

[0036] In a three-necked round-bottomed flask, add 50-85mL of 36%-40% formaldehyde aqueous solution, add 80-140g of diethylamine dropwise under the condition of cooling in an ice bath, and keep the reaction temperature at 15°C-35°C. After the dropwise addition is completed, React at room temperature for 2-6 hours, the solution appears to be stratified, the upper layer is an organic layer, and the lower layer is a water layer. Move the solution to a separatory funnel, separate the upper organic layer, dry it with anhydrous sulfuric acid, place it, filter it, and then conduct normal ...

Embodiment 33

[0045] The synthesis of embodiment 3'-methylene-morpholine-puerarin

[0046] Morpholine first undergoes a Mannich reaction with formaldehyde to generate methylene-morpholine, and then methylene-morpholine undergoes a condensation reaction with puerarin at the ortho position of the phenolic hydroxyl group to generate 3′-methylene-morpholine-puerarin.

[0047] (1) Synthesis of 4-4'-methylenebismorpholine

[0048] Add 20-50g morpholine into a three-neck round bottom flask, slowly add 10-25g 36%-40% formaldehyde solution dropwise with a dropping funnel, and at the same time cool in a water bath to control the reaction temperature not exceeding 50°C, after the dropwise addition, stir at room temperature After standing for 0.5-3.5 hours, the solution appears to be stratified. The upper layer is organic matter, and the lower layer is water. Move it to a separatory funnel to separate the upper layer, add anhydrous potassium carbonate to dry, filter, then distill under reduced pressure...

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Abstract

The invention provides a synthetic method of puerarin derivatives, which relates to the field of compound synthesis. At present, a main functional group, i.e. a phenolic hydroxyl group of puerarin, is combined or shielded in the puerarin structure transformation and modification, and the biological activity of matters is lowered. Secondary amine firstly carries out Mannich reaction with formaldehyde so as to generate Mannich alkali, and the Mannich alkali carries out condensation reaction with the adjacent position of the phenolic hydroxyl group of the puerarin so as to generate the puerarin derivatives. The synthetic method of puerarin derivatives not only avoids combining or shielding the main functional group, i.e. the phenolic hydroxyl group of the puerarin, but also provides a new method for the structure qualification of isoflavonoid.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to the synthesis of puerarin derivatives. Background technique [0002] Puerarin is a flavonoid glycoside extracted from the dried root of Pueraria lobata (wild.) Ohwi or Puerariathomsonii Benth., the chemical name of which is 4′, 7-dihydroxy-8 -D-glucosyl isoflavones. Pharmacological experiments show that puerarin has the functions of reducing vascular resistance, improving cerebral and coronary circulation, reducing myocardial oxygen consumption, etc., and has a good preventive effect on retinal embolism, myocardial infarction and other diseases. However, due to the poor water solubility and fat solubility of its isoflavone structure, its bioavailability is low, which limits its biological activity and clinical application. Therefore, finding a suitable method to improve the fat-solubility and water-solubility of puerarin is of great significance for improving its bioavailabili...

Claims

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Application Information

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IPC IPC(8): C07H17/07A61P9/00
Inventor 梁剑平王曙阳郭志廷郭文柱尚若峰刘宇王学红郭延生华兰英
Owner LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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