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Adamantine amino tea sapogenol as well as preparation method and application thereof

A technology of adamantyl amino and tea soap, which is applied in the field of medicine, can solve the problems of mental side effects, decline and loss of curative effect, and achieve the effect of high product purity, simple preparation process and small structure

Inactive Publication Date: 2013-02-13
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Drugs for treating Parkinson's disease mainly include dopamine-like drugs or dopamine potentiators, but their curative effect will decrease or lose after long-term use, and they may have psychoactive side effects
There is no report about the neuroprotective effect of tea saponin

Method used

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  • Adamantine amino tea sapogenol as well as preparation method and application thereof
  • Adamantine amino tea sapogenol as well as preparation method and application thereof
  • Adamantine amino tea sapogenol as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 100g of teasapogenin solid into 300mL of pyridine, heat to 50°C to dissolve it; add triphenylchloromethane (56.7g) according to the equimolar amount of teasapogenin, keep warm at 50°C and stir for 8h; add teasapogenin 2 times the molar mass of acetic anhydride (41.6g), stirred and reacted at 50°C for 15h; added 9.4mL of formic acid, the reaction temperature was 100°C, and refluxed for 1h; after cooling to 20°C, added 45.6g of amantadine hydrochloride, triphenylphosphine 0.5g, 0.5g dimethyl azodicarboxylate, stir for 9h; add 56g of potassium carbonate, stir for 1h, evaporate pyridine under reduced pressure, add 1000mL water to wash, add toluene to wash the water-insoluble matter, and dissolve the residue with methanol and crystallized and dried in vacuo to yield 28 g of product.

[0034] The structural analysis of the product shows that MS: m / z 623; the elemental composition is: C77.00%, H10.50%, N2.24%, 010.26%, and its molecular formula is C 40 h 65 NO 4 , 1 H-...

Embodiment 2

[0036] Add 100g of teasapogenin solid into 300mL pyridine, dissolve it at room temperature (25°C), add triphenylchloromethane (85g) according to 1.5 times the molar mass of teasapogenin, keep warm at 25°C and stir for 12h; Acetic anhydride (83.2g) with 3 times the molar mass was stirred and reacted at 70°C for 10h; 14mL of formic acid was added, the reaction temperature was 105°C, and refluxed for 1h; after cooling to 25°C, 45.6g of amantadine, triphenylphosphine 10g, 10g of dimethyl azodicarboxylate, stirred for 6h; added 112g of potassium carbonate, stirred for 1h, evaporated pyridine under reduced pressure, added 1000mL of water to wash, then added toluene to wash, the residue was dissolved in methanol and crystallized, dried in vacuo , 45 g of product were obtained.

[0037] The analytical data of the product structure is the same as in Example 1, proving that the structure of the final product is as shown in Formula I.

Embodiment 3

[0039] Add 100g of teasapogenin solid into 300mL of pyridine, heat to 40°C to dissolve, add triphenylchloromethane (68g) according to 1.2 times the molar mass of teasapogenin, keep warm at 40°C and stir for 16h; add teasapogenin 4 times the molar mass of acetic anhydride (62.4g), stirred and reacted at 80°C for 8h; added 11.3mL of formic acid, the reaction temperature was 110°C, and refluxed for 1h; after cooling to 30°C, added 45.6g of amantadine, triphenylphosphine 3g, 3g of dimethyl azodicarboxylate, stirred for 3h; added 84g of potassium carbonate, stirred for 1h, evaporated pyridine under reduced pressure, added 1000mL of water to wash, then added toluene to wash, the residue was dissolved in methanol and crystallized, and dried in vacuo , 37 g of product were obtained.

[0040] The analytical data of the product structure is the same as in Example 1, proving that the structure of the final product is as shown in Formula I.

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Abstract

The invention discloses adamantine amino tea sapogenol as well as a preparation method and application thereof. The adamantine amino tea sapogenol has a structure shown as a formula I and can be prepared by the following steps of: reacting triphenyl chloromethane with tea saponin element and connecting triphenylmethyl to a primary hydroxyl of the tea saponin element C28; reacting acetic anhydride with the tea saponin element and connecting acetyl to a secondary hydroxyl of the tea saponin element; adding a triphenylmethyl protective agent and reacting with the tea saponin element to remove the triphenylmethyl on the tea saponin element; reacting and connecting the tea saponin element with adamantine under the condition that a catalyst exists; and finally, adding an acetyl deprotection agent to remove the acetyl on the tea saponin element and obtaining the adamantine amino tea sapogenol shown as the formula I by crystallization. The invention has the advantages of simple preparation process, mild reaction conditions and high purity of products and can be used for industrial production; and the obtained adamantine amino tea sapogenol has a small structure and the protective activity of the adamantine amino tea sapogenol on nervous centralis is remarkably improved.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a theosapogenin derivative adamantylaminotheasapogenol with neuroprotective effect, its preparation method, and its application as an anti-neurodegenerative disease drug. Background technique [0002] Neurodegenerative diseases are diseases caused by the degeneration of nerve tissue caused by various reasons. Pathologically, the reduction and degeneration of neurons in the brain and spinal cord can be seen. Typical neurodegenerative diseases include Parkinson's disease, Alzheimer's disease, etc., and their pathogenesis is still not very clear. At present, several theories such as excitotoxicity, oxidative stress, and apoptosis are mainly used to explain the pathogenesis. Experiments often use poisoning, ischemic injury and other models to study the neuroprotective effect of drugs. [0003] So far, there are no very effective drugs for the treatment of neurodegenerative diseases. Drugs f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/56A61P25/00A61P25/28A61P25/16
Inventor 叶勇罗月婷
Owner SOUTH CHINA UNIV OF TECH
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