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Tea saponin derivative with anti-inflammatory analgesic efficacy, preparation method and application thereof

A tea sapogenin, anti-inflammatory and analgesic technology, applied in the field of medicine, can solve the problems affecting clinical application, low analgesic titer, etc., and achieve the effects of easy control of reaction conditions, high analgesic activity, and guaranteed consistency

Inactive Publication Date: 2013-04-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although tea saponins have a certain analgesic effect, their analgesic potency is low, which affects their clinical application.

Method used

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  • Tea saponin derivative with anti-inflammatory analgesic efficacy, preparation method and application thereof
  • Tea saponin derivative with anti-inflammatory analgesic efficacy, preparation method and application thereof
  • Tea saponin derivative with anti-inflammatory analgesic efficacy, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Theosapogenin (C 30 h 50 o 5 ) solid 100g, added to 300mL of pyridine, heated to 50°C to dissolve, added triphenylchloromethane (56.7g) according to the equimolar amount of tea saponin, kept stirring at 50°C for 8h; added triphenylchloromethane 1 / 5 mass of potassium hydroxide (11.3g), heated to 80°C, stirred for 1h, evaporated under reduced pressure to remove water and pyridine, added 500mL of toluene to dissolve, heated to 120°C, slowly added dropwise Benzyl bromide (140g), stirred and reacted for 8h; Naproxen (46.9g) was added in an equimolar amount of teasapogenin, and 12mL of formic acid was refluxed for 5h; The catalyst was fed with hydrogen for 3 hours, and the precipitate was crystallized with ethanol water to obtain 73 g of the product.

[0038] The structural analysis of the product shows that MS: m / z 674; the elemental composition is: C74.74%, H8.66%, O16.59%, and its molecular formula is C 42 h 58 o 7 , 1 H-NMR with 13 The hydrogen and carbon signals ...

Embodiment 2

[0041] Theosapogenin (C 30 h 50 o 5 ) solid 100g, was added to 300mL of pyridine, dissolved at room temperature (25°C), triphenylchloromethane (85g) was added according to 1.5 times the molar amount of tea saponin, and stirred for 16h; triphenylchloromethane was added for 1 / 5 mass of potassium hydroxide (17g), heat up to 80°C, stir for 1h, evaporate water and pyridine under reduced pressure, add 500mL toluene to dissolve, heat up to 140°C, slowly add benzyl bromide with 5 times the molar mass of tea saponin (174g), stirring reaction 6h; Add the naproxen (46.9g) of tea saponin equimolar amount, formic acid 18mL reflux divides water 3h; Reactant is placed in pressure reactor, is catalyst with 10% palladium carbon, Hydrogen was introduced for 3 hours, and the precipitate was crystallized with ethanol water to obtain 84 g of the product.

[0042] The analysis data of the product structure is the same as that in Example 1, which proves that the final product is naproxenate thea...

Embodiment 3

[0044] Theosapogenin (C 30 h 50o 5 ) solid 100g, added to 300mL of pyridine, heated to 40°C to dissolve, added triphenylchloromethane (68g) according to 1.2 times the molar mass of tea saponin, kept stirring at 40°C for 12h; added triphenylchloromethane 1 / 5 mass of potassium hydroxide (13.6g), heated to 80°C, stirred for 1h, evaporated under reduced pressure to remove water and pyridine, added 500mL of toluene to dissolve, heated to 130°C, slowly added dropwise 4.5 times the molar amount of tea saponin Benzyl bromide (157g), stirred and reacted for 7h; Naproxen (46.9g) was added in an equimolar amount of teasapogenin, and 15mL of formic acid was refluxed for water separation for 4h; The catalyst was fed with hydrogen for 3 hours, and the precipitate was crystallized with ethanol water to obtain 68 g of the product.

[0045] The analysis data of the product structure is the same as that in Example 1, which proves that the final product is naproxenate theasapogenol ester.

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Abstract

The invention discloses a tea saponin derivative with anti-inflammatory analgesic efficacy, a preparation method and application thereof. The structural formula of the tea saponin derivative with anti-inflammatory analgesic efficacy is shown in formula I. The tea saponin derivative is prepared by the following steps of: reacting triphenylmethyl chloride with tea saponin; adding benzyl bromide to react with the tea saponin; adding a trityl deprotection agent, naproxen or acetylsalicylic acid to react with the tea saponin; finally adding a benzyl deprotection agent, reacting with the tea saponin under the action of a catalyst for deproteinizing benzyl on the tea saponin; and crystallizing to obtain the tea saponin derivative which is shown in the formula I and has anti-inflammatory analgesic efficacy. The invention has the advantages of simple preparation technology and easily controlled reaction conditions, and is suitable for industrial production. The obtained tea saponin derivative has high anti-inflammatory analgesic activity and overcomes the defect of lower analgesic potency of the tea saponin.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a teasapogenin derivative, a preparation method thereof, and an application thereof as an anti-inflammatory and analgesic drug. Background technique [0002] Pain is a defense response of the body to noxious stimuli, and it is also one of the common symptoms of many diseases. Pain not only makes patients feel miserable, but may also cause physiological dysfunction. Severe pain can even lead to shock. Therefore, drugs must be used rationally to relieve pain and prevent possible physiological dysfunction. At present, the analgesics used clinically mainly include opioid analgesics and non-opioid analgesics. Although the former has better analgesic effect, it is prone to dependence after long-term use, so it is strictly regulated in clinical application. Restrictions; the latter are mainly antipyretic and analgesic drugs such as aspirin, which are limited to the treatment of mild pain. [0...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/56A61K31/621A61P29/00
Inventor 叶勇王延芳
Owner SOUTH CHINA UNIV OF TECH
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