Coumarin glycoside compound, its preparation method, pharmaceutical composition and application

A compound and composition technology, applied in the field of novel coumarin glycosides, can solve the problems of affecting clinical efficacy, low bioavailability, poor fat solubility and the like

Active Publication Date: 2019-01-01
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because its structure contains a glucose and phenolic hydroxyl group, its fat solubility is poor and its bioavailability is low, which affects the clinical efficacy.

Method used

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  • Coumarin glycoside compound, its preparation method, pharmaceutical composition and application
  • Coumarin glycoside compound, its preparation method, pharmaceutical composition and application
  • Coumarin glycoside compound, its preparation method, pharmaceutical composition and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 16

[0067] The synthesis of embodiment 16'-O-cinnamic acid inuroside (I-a)

[0068] In a dry 5ml round-bottomed flask, add 74mg (0.5mmol) of dry cinnamon acid, dissolve it in anhydrous dichloromethane, add 126mg (100ul, 1.0mmol) of oxalyl chloride dropwise under stirring at room temperature, after the addition is complete, add one drop Anhydrous DMF, catalytic reaction. The reaction was carried out for 1 h, and the reaction was detected by TLC. After the reaction was completed, the reaction solution was concentrated and evaporated to dryness. That is, cinnamon acid chloride. Dissolve with anhydrous DMF for later use.

[0069] In a dry 5ml round bottom flask, add 194mg (0.6mmol) of dry inuroside, dissolve it with anhydrous pyridine, and add the DMF solution of cinnamoyl chloride dropwise under stirring at room temperature, and drop it in about 20 minutes. Reaction at room temperature, TLC detection reaction. After stopping the reaction, the reaction solution was concentrated a...

Embodiment 26

[0071] Example 26'-O-Synthesis of p-hydroxycinnamic acid interoside (I-b)

[0072] In a dry 5ml round bottom flask, add 82mg (0.5mmol) of dry p-hydroxycinnamic acid, dissolve it with anhydrous dichloromethane, add 126mg (100ul, 1.0mmol) of oxalyl chloride dropwise under stirring at room temperature, after the dropwise addition, Add a drop of anhydrous DMF to catalyze the reaction. The reaction was carried out for 1 h, and the reaction was detected by TLC. After the reaction was completed, the reaction solution was concentrated and evaporated to dryness. That is, p-hydroxycinnamic acid chloride. Dissolve with anhydrous DMF for later use.

[0073] In a dry 5ml round bottom flask, add 194mg (0.6mmol) of dry innoside, dissolve it with anhydrous pyridine, add the DMF solution of p-hydroxycinnamoyl chloride dropwise under stirring at room temperature, and drop it in about 20 minutes. Reaction at room temperature, TLC detection reaction. After stopping the reaction, the reaction...

Embodiment 36

[0075] Example 3 Synthesis of 6'-O-indioside ferulate (I-c)

[0076] In a dry 5ml round bottom flask, add 97mg (0.5mmol) of dry ferulic acid, dissolve it with anhydrous dichloromethane, add 126mg (100ul, 1.0mmol) of oxalyl chloride dropwise under stirring at room temperature, after the dropwise addition, add A drop of anhydrous DMF catalyzes the reaction. The reaction was carried out for 1 h, and the reaction was detected by TLC. After the reaction was completed, the reaction solution was concentrated and evaporated to dryness. That is, feruloyl chloride. Dissolve with anhydrous DMF for later use.

[0077] In a dry 5ml round bottom flask, add 194mg (0.6mmol) of dry inuroside, dissolve it with anhydrous pyridine, and add the DMF solution of feruloyl chloride dropwise under stirring at room temperature, and drop it in about 20 minutes. Reaction at room temperature, TLC detection reaction. After stopping the reaction, the reaction solution was concentrated and separated by r...

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Abstract

The invention relates to a novel coumarin glycoside compound derived from esculine or skimmin and a synthesis method thereof, and application of the novel coumarin glycoside compound and 7-O-methylesculine as drugs in diseases related to diabetic angiopathies. The in-vitro activity evaluation shows that the compound has obvious free radical removal action and ADP (adenosine diphosphate)-induced platelet aggregation inhibition action. The overall animal drug effect evaluation experiment result indicates that the 7-O-methylesculine can resist experimental hyperlipemia and inhibit atherosclerosis from formation, has obvious higher activity than esculine, and has application prospects in the aspect of resisting diseases related to diabetic angiopathies.

Description

Technical field: [0001] The present invention relates to a novel coumarin glycoside compound derived from aesculetin or innoside and a synthesis method thereof, as well as the use of 7-O-methylaurinine as a medicine in diseases related to diabetic vascular lesions. Background technique: [0002] Diabetes is a group of clinical syndromes caused by the interaction of genetic and environmental factors. It has become the third major disease that seriously threatens human health after heart disease and cancer. It causes a series of complications such as cardiovascular and cerebrovascular diseases , nerve series complications, body damage, high blood pressure, ketoacidosis, etc., will have serious consequences of disability, blindness, and death. The medical expenses required for the prevention and treatment of cardiovascular and cerebrovascular diseases account for the most important part of the medical expenses of diabetes. Therefore, diabetic vascular disease-related diseases ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/075C07H1/00A61K31/7048A61P3/10A61P3/06A61P9/00A61P9/10A61P7/02A61P39/06
CPCA61K31/7048C07H1/00C07H17/075
Inventor 张东明杜冠华王月华时静杨敬芝
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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