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3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative, as well as preparation method and application thereof

A kind of technology of uronic acid oxyglycoside oleanane and ursane type, which is applied in the field of 3-monouronic acid oxyglycoside oleanane type and ursane type triterpene saponin derivatives and their preparation, capable of Solve the problems of low bioavailability and poor solubility, and achieve the effects of enhancing anti-arrhythmic activity, good myocardial protection, and high product purity

Inactive Publication Date: 2015-12-02
INST OF MEDICINAL PLANT DEV CHINESE ACADEMY OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the biological activity of oleanolic acid 3-O-β-D-glucopyranoside still needs to be improved, and the solubility is poor and the bioavailability is not high

Method used

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  • 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative, as well as preparation method and application thereof
  • 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative, as well as preparation method and application thereof
  • 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 Preparation of Derivatives CHA-1 and CHA-2

[0034]

[0035] Step a'-step d': Preparation of glucose trichloroacetimidate (5')

[0036] Under an ice-water bath, dissolve D-glucose (5.0 g, 27.7 mmol) in 100 mL of dry pyridine, add benzoyl chloride (19.3 mL, 166.5 mmol), stir and react at room temperature for 18 h, add 60 mL of water to destroy excess benzoyl chloride, and Extract with ethyl acetate, combine the organic phases, wash with water, dilute hydrochloric acid, and saturated sodium bicarbonate in sequence, dry over anhydrous magnesium sulfate, filter, and concentrate the filtrate to obtain 18.7 g of perbenzoylated glucose (2').

[0037] Dissolve 4.0 g of perbenzoylated glucose (2') obtained in the previous step in 40 mL of dry dichloromethane, add 12 mL of HBr-HOAc dropwise, and stir the reaction at room temperature. Washed with sodium solution and brine, and the organic layer was concentrated to dryness to obtain the glucose-terminal brominated pro...

Embodiment 2

[0053] Embodiment 2 prepares derivative CHA-3

[0054]

[0055] The product oleanolic acid-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside) (O-3)( 500mg, 0.488mmol) was dissolved in 5mL of dry dichloromethane, EDCI (140mg, 0.732mmol) and HOBT (98.8mg, 0.732mmol) were added and stirred at room temperature for 2h, and cyclohexylamine (1.64mmol ), the reaction was continued for 4 h at room temperature. After the completion of the reaction was monitored by TLC, it was washed with 0.1N dilute hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride in sequence, and dried overnight with anhydrous sodium sulfate. Suction filtration, evaporated to dryness under reduced pressure, then dissolved in 5mL dry methanol and dichloromethane (v / v=3:1), added 0.8mL sodium methoxide methanol (1mol / L) solution, reacted at room temperature for 6h. After the reaction, use 732-type cation exchange resin to adjust the pH to neutral, filter and evaporate to ...

Embodiment 3

[0057] Embodiment 3 prepares derivative CHA-5

[0058]

[0059]1) The preparation of galactose trichloroacetimide ester is similar to the preparation method of glucose trichloroacetimide ester in Example 1. Under an ice-water bath, D-galactose (5.0 g, 27.7 mmol) was dissolved in 100 mL of dry pyridine , add benzoyl chloride (19.3mL, 166.5mmol), stir at room temperature for 18h, add 60mL of water to destroy excess benzoyl chloride, extract with ethyl acetate, combine organic phases, wash with water, dilute hydrochloric acid, saturated sodium bicarbonate in sequence , dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to obtain 15.9 g of perbenzoylated galactose. Dissolve 4.0 g of perbenzoylated galactose obtained in the previous step in 40 mL of dry dichloromethane, add 12 mL of HBr-HOAc dropwise, and stir the reaction at room temperature. After 1 hour of reaction, the reaction solution is washed with saturated sodium bicarbonate solution, A...

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Abstract

The invention discloses a 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative. The derivative has a structural formula as shown in the specification, wherein R4 is one of H atom, alkyl containing 1-10 carbons, alkyl amido containing 1-10 carbons, aryl containing 6-11 carbons and saturated or unsaturated ring containing 3-7 carbon atoms. According to the preparation method, oleanolic acid or ursolic acid is used as a lead compound, and is structured to synthesize a novel 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative. The synthesizing method is simple and convneient, the product has high purity, and the anti-arrhythmia activity of the 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative is remarkably enhanced by means of structure transformation. The 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative has a relatively good cardiac muscle protecting effect.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and therapeutics, in particular to a 3-monouronic acid oxyglycoside oleanane-type and ursane-type triterpene saponin derivatives and a preparation method and application thereof. Background technique [0002] Cardiovascular disease is a serious threat to human health and life. Although great progress has been made in the prevention and treatment of cardiovascular disease in medicine, surgery, etc., the disability and death rate of the disease is still increasing year by year. The prevention and treatment of myocardial ischemia, myocardial infarction and their complications are the hotspots of current medical research. Clinically, thrombolysis-based treatment for acute and severe patients has bleeding restrictions and risks, so it is currently recognized as a Safe and effective prevention and treatment drugs are drugs with cardioprotective effect. [0003] Liaodong Aralia [Araliaelata (Miq) See...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61P9/10
Inventor 许旭东田瑜孙桂波孙晓波王敏
Owner INST OF MEDICINAL PLANT DEV CHINESE ACADEMY OF MEDICAL SCI
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