Alpha-glycosidase inhibitor preparation method and purpose

A technology of glucosidase and inhibitory activity, which can be used in pharmaceutical formulations, medical preparations containing active ingredients, metabolic diseases, etc., and can solve problems such as high economic pressure

Inactive Publication Date: 2013-06-19
GUANGXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the α-glucosidase inhibitors used in the domestic diabetes drug market are mainly imported drugs, which are re

Method used

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  • Alpha-glycosidase inhibitor preparation method and purpose
  • Alpha-glycosidase inhibitor preparation method and purpose
  • Alpha-glycosidase inhibitor preparation method and purpose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment one: the synthesis of berberine (I)

[0024] 10 g (50 mmol) of berberine hydrochloride was decompressed to 20-30 mmHg in a vacuum oven, heated to 190° C. and reacted for 2 h to obtain the target product with a yield of 78%. m.p.169-172°C.

Embodiment 2

[0025] Embodiment two: the synthesis of 9'-O-berberine ethyl acetate hybrid (II)

[0026] Take 5.4g (15mmol) of refined berberine, place it in a dry 250mL round bottom flask with a magnet, add 100mL DMF, dissolve it completely, add 3g of anhydrous K 2 CO 3 , stirred at room temperature for 0.5 h, slowly added 3 g (18 mmol) of ethyl bromoacetate dropwise, continued to stir the reaction, and tracked the reaction with TLC. After the reaction is complete, the reaction solution is filtered, the filter cake is washed with a small amount of DMF, and methanol-chloroform is used as the eluent, and the filtrate is separated by column chromatography on silica gel to obtain 2.77 g of a light yellow solid, and the yield is 42%. m.p.189~191℃.

Embodiment 3

[0027] Embodiment three: the synthesis of 9'-O-berberine hydrazide (III)

[0028] 1.54g (3.46mmol) of compound II, 0.24g (4.16mmol) of 85% hydrazine hydrate, and 40mL of ethanol were stirred and refluxed in a 100mL three-necked flask for 2h, followed by TLC until the end of the reaction. Crystallized by cooling, filtered to obtain 1.16g of crude product, recrystallized with absolute ethanol, dried to obtain 125g of white solid, yield 78.0%, m.p.210-212°C.

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Abstract

The invention discloses a preparation method of an alpha-glycosidase inhibitor 2,3,4-trihydroxy benzaldehyde-9'-O-berberine acylhydrazone, and can be used for preparing the medicines to treat diabetes. A structural formula of a compound is shown in the description. The preparation method comprises the following steps: 1) taking berberine hydrochloride as an initial raw material, demethylating under pressure reduction 190 DEG C condition, wherein the products can not be separated to obtain berberrubine (I), bridging the obtained compound I and alpha-ethyl bromoacetate through a nucleophilic substitution reaction to form a berberine ethyl acetate derivative (II); 2) performing hydrazinolysis of the compound II and hydrazine hydrate to obtain berberine hydrazides (III); and 3) performing nucleophilic addition-dehydration reaction on the compound III and the 2,3,4-trihydroxy benzaldehyde to obtain the 2,3,4-trihydroxy benzaldehyde-9'-O-berberine acylhydrazone (TM), and purifying the products through a recrystallization method. The 2,3,4-trihydroxy benzaldehyde-9'-O-berberine acylhydrazone has strong alpha-glucosidase inhibition activity through alpha-glucosidase inhibition experiment, and its inhibition performance is higher than that of a comparison product acarbose by 1.2 times.

Description

technical field [0001] The invention relates to a preparation method of 2,3,4-trihydroxybenzaldehyde-9'-O-berberine acylhydrazone. The derivative can be used as an alpha-glucosidase inhibitor and can be used for treating diabetes. Background technique [0002] Diabetes is a metabolic disorder of sugar, protein and fat. Its etiology and pathogenesis have not been fully elucidated, mainly due to abnormal secretion or production of insulin. Clinically, it is manifested as polydipsia, polyuria, polyphagia, weight loss, etc . Type 2 diabetes is adult-onset diabetes, mostly after the age of 35 to 40, accounting for more than 90% of diabetic patients. Type 2 diabetes is a chronic endocrine disease, mainly caused by insulin resistance or insufficient insulin secretion. Patients with type 2 diabetes mainly have three metabolic abnormalities: abnormal insulin secretion, increased hepatic glucose release, and decreased insulin sensitivity. Chronic hyperglycemia can lead to damage to ...

Claims

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Application Information

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IPC IPC(8): C07D455/03A61K31/4375A61P3/10
Inventor 霍丽妮陈睿李培源苏炜
Owner GUANGXI UNIV OF CHINESE MEDICINE
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