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

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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

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Examples

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Example Embodiment

[0019] Example 13 The synthesis of methylene-dimethylamine-puerarin

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

[0021] (1) Preparation of dimethylamine aqueous solution

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

[0023] (2) Synthesis of bis-(dimethylamine) methane

[0024] Under ice-bath cooling, add 5-25ml of 37%-40% formaldehyde aqueous solution to a 100ml three-necked round bottom flask, while stirring, add 0.25-0.45mol of dimethylamine aqueous solution (add dropwise with a dropping funnel, Keep the reaction temperature below 50°C), after the addition, stir at room temperature for 15-45 minutes, then add solid NaOH to the solution to form two phases, separate the ...

Example Embodiment

[0033] Example 23 Synthesis of',5'-methylene-diethylamine-puerarin

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

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

[0036] In a three-necked round-bottom flask, add 50-85mL of 36%-40% formaldehyde aqueous solution, add 80-140g of diethylamine dropwise while cooling in an ice bath, and maintain the reaction temperature at 15°C-35°C. The addition is complete. After reacting at room temperature for 2-6 hours, the solution layered, the upper layer is the organic layer, and the lower layer is the water layer. Transfer the solution to a separatory funnel, separate the upper organic layer, dry with anhydrous sulfuric acid, place, filter, and then proceed to normal Pressure distillation, collect the 158℃-160℃ fraction; its synthesis rou...

Example Embodiment

[0045] Example 33'-Methylene-morpholine-puerarin synthesis

[0046] Morpholine first undergoes Mannich reaction with formaldehyde to form methylene-morpholine, and then methylene-morpholine undergoes condensation reaction with puerarin phenolic hydroxyl group to produce 3′-methylene-morpholine-puerarin.

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

[0048] Add 20-50g morpholine to a three-necked round-bottom flask, slowly add 10-25g 36%-40% formaldehyde aqueous solution with a dropping funnel while cooling in a water bath to control the reaction temperature not to exceed 50℃. After the addition is complete, stir at room temperature Leave it for 0.5-3.5 hours, and the solution will be stratified. The upper layer is organic and the lower layer is water. Transfer to a separatory funnel to separate the upper layer, add anhydrous potassium carbonate to dry, filter, and then distill under reduced pressure to collect 90℃-92℃ The distillate is colorless; its synthesis route is as...

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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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