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Chemically modified ursolic acid and its preparation method and use

A technology of chemical and chemical modification of ursolic acid, which is applied in the field of drug synthesis, can solve the problem of low inhibitory activity of α-glucosidase, and achieve the effects of wide application range, high synthesis yield and high biological activity

Active Publication Date: 2014-09-17
INT HEALTHCARE INNOVATION INST JIANGMEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the α-glucosidase inhibitory activity of ursolic acid, especially its derivatives, is rarely reported.

Method used

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  • Chemically modified ursolic acid and its preparation method and use
  • Chemically modified ursolic acid and its preparation method and use
  • Chemically modified ursolic acid and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0048]Example 13 Preparation of β-acetoxy-ursane-12-ene-28-carboxylic acid (compound 2):

[0049] First weigh 6mmol of ursolic acid (UA) into a 125mL round-bottomed flask containing magnets, then measure 75mL of dry pyridine into the flask, stir for about 10min at room temperature until it is completely dissolved, then add 60mg of 4-dimethyl Aminopyridine was stirred and dissolved, and then 24mmol (four times the amount) of acetic anhydride was slowly added dropwise, and reacted for 12 hours at room temperature, and the end point of the reaction was detected by TLC (developing agent: petroleum ether: ethyl acetate (volume ratio) = 5 :1, developer: methanol: acetic acid: concentrated sulfuric acid: anisaldehyde (volume ratio) = 85:10:5:0.5). After the reaction was completed, pyridine was distilled off under reduced pressure at 55° C., and then the reaction system was dispersed with 100 mL of distilled water, suction filtered, and repeated three times to collect the solid layer....

Embodiment 23

[0050] Example 23 Preparation of β-propionyloxy-ursane-12-ene-28-carboxylic acid (compound 3):

[0051] First weigh 6mmol of ursolic acid (UA) into a 125mL round-bottomed flask containing magnets, then measure 75mL of dry pyridine into the flask, stir at room temperature for about 10min until it is completely dissolved, then add 60mg of 4-dimethylamino Stir to dissolve pyridine, then slowly add 24 mmol (four times the amount) of propionic anhydride dropwise, react at room temperature for 12 hours, and detect the end of the reaction with TLC (developing agent: petroleum ether: ethyl acetate (volume ratio) = 5:1 , Chromogenic agent: methanol: acetic acid: concentrated sulfuric acid: anisaldehyde (volume ratio) = 85:10:5:0.5), the reaction is completed, at 55 ° C, evaporate pyridine under reduced pressure, and then disperse the reaction system with 100mL distilled water, Suction filtration was repeated three times to collect the solid layer. Disperse the solid with 100 mL of wat...

Embodiment 33

[0052] Example 33 Preparation of β-butyryloxy-ursane-12-ene-28-carboxylic acid (compound 4):

[0053] First weigh 6mmol of ursolic acid (UA) into a 125mL round-bottomed flask containing magnets, then measure 75mL of dry pyridine into the flask, stir at room temperature for about 10min until it is completely dissolved, then add 60mg of 4-dimethylamino Stir to dissolve pyridine, then slowly add 24 mmol (four times the amount) of butyric anhydride dropwise, react at room temperature for 12 hours, and detect the end of the reaction with TLC (developing agent: petroleum ether: ethyl acetate (volume ratio) = 5:1 , Chromogenic agent: methanol: acetic acid: concentrated sulfuric acid: anisaldehyde (volume ratio) = 85:10:5:0.5), the reaction is completed, at 55 ° C, evaporate pyridine under reduced pressure, and then disperse the reaction system with 100mL distilled water, Suction filtration was repeated three times to collect the solid layer. Disperse the solid with 100 mL of water a...

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Abstract

The invention discloses chemically modified ursolic acid and its preparation method and use. The chemically modified ursolic acid has a structural formula shown in the following formula, and in the formula, R1 represents acyloxy and R2 represents an amino group. The preparation method comprises the following steps that ursolic acid and acid anhydride undergo a reaction under the catalyst condition to produce 3 beta-acyloxy-ursane-12-ene-28-carboxylic acid compounds 2-5, the compounds 2-5 are acylated by oxalyl chloride under the ice bath condition to form 3-acetoxy-ursane-12-ene-28-acyl chloride, and the 3-acetoxy-ursane-12-ene-28-acyl chloride and aniline undergo a reaction under the acid binding agent condition to produce N-(3 beta-acyloxy-ursane-12-ene-28-acyl)-amine compound. The N-(3 beta-acyloxy-ursane-12-ene-28-acyl)-amine compound has enzymatic activity inhibition effects, can be used in drugs, drinks, foods and health products for preventing, controlling or treating high-blood sugar level diabetes or obesity and belongs to the technical field of drug synthesis.

Description

technical field [0001] The invention discloses a chemically modified ursolic acid, and also discloses the chemically modified ursolic acid, its preparation method and application; it belongs to the technical field of medicine synthesis. Background technique [0002] Diabetes is a common endocrine and metabolic chronic disease that occurs when the pancreas cannot produce enough insulin or when the body cannot effectively use the insulin it produces. Insulin is a hormone that regulates blood sugar. Hyperglycemia, or elevated blood sugar, is a common result of uncontrolled diabetes and over time can cause serious damage to many systems in the body, especially the nerves and blood vessels. In developed countries, diabetes is the third "killer" that endangers human health after cardiovascular and cerebrovascular diseases and cancer. [0003] According to the report of the World Health Organization in March 2013, there are about 347 million people with diabetes worldwide. Accor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61P3/04A61P3/10A23L1/30A23L2/52
Inventor 赵肃清吴盼盼张焜何萍黄天明罗健程安明
Owner INT HEALTHCARE INNOVATION INST JIANGMEN
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