Shikonin carbohydrate derivatives and synthetic method and use thereof

The technology of a carbohydrate derivative and a synthesis method is applied in synthesis and its application in tumor suppression, and can solve problems such as side effects and obvious morphine addiction.

Inactive Publication Date: 2009-03-25
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Taxol, camptothecin, morphine, etc. are all drugs that have been used clinically for a long time, but the side effects gradually appear during the use, especially the addiction of morphine is obvious

Method used

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  • Shikonin carbohydrate derivatives and synthetic method and use thereof
  • Shikonin carbohydrate derivatives and synthetic method and use thereof
  • Shikonin carbohydrate derivatives and synthetic method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0032] Example 1: Shicaoning preparation method

[0033] Take the bruised tissue culture solution of Lilacia yunnanensis cultivated in the dark, and extract it three times with petroleum ether with a boiling range of 60-90°C until it becomes colorless. The extracts were combined, and the solvent was concentrated under reduced pressure to obtain a black-red paste, which was dissolved by adding chloroform, and an appropriate amount of silica gel was added, and the solvent was evaporated to dryness, followed by column chromatography. The chromatographic column is packed with 200-300 mesh silica gel, and the column chromatography is carried out with ethyl acetate:petroleum ether=1:7 to obtain pure shikonin.

example 2

[0034] Example two: the synthetic method of formula I class shikonin derivatives

[0035] Take 0.5mmol of shikonin and 0.4mmol of fully acetylated mercapto sugar compound and dissolve them in 20ml of ethanol solution, stir and react at room temperature at 0°C to 30°C until the point of sugar compound disappears, followed by TLC detection. Add an appropriate amount of silica gel to concentrate the solvent under reduced pressure, and perform column chromatography with ethyl acetate:petroleum ether=1:2 to obtain the glycosyl shikonin derivative with a yield of about 85%.

[0036] The reaction takes glucose as an example:

[0037]

[0038] Compound 1

[0039] Compounds 2-7 can be obtained in the same way.

[0040]

[0041] Compound 2 Compound 3 Compound 4 Compound 5

[0042]

[0043] Compound 6 Compound 7

example 3

[0044] Example 3: Synthesis of Formula I Deprotected Glycosyl Shikonin Derivatives

[0045] Dissolve 0.1mmol of compound 1 in 5ml of acetonitrile, add an appropriate amount of concentrated ammonia water dropwise at a temperature ranging from -4°C to 5°C, react until the raw material point disappears, neutralize it with dilute hydrochloric acid, add 0.05g of silica gel to the product and evaporate it to dryness naturally, then wash with ethanol : Chloroform=1:5 column chromatography, the product was obtained, and the yield was 90%.

[0046] The reaction takes glucose as an example:

[0047]

[0048] Compound 8

[0049] Compounds 9-14 can be obtained by the same method.

[0050]

[0051] Compound 9 Compound 10 Compound 11 Compound 12

[0052]

[0053] Compound 13 Compound 14

[0054] Example 4. Application of Formula I Shikonin Saccharide Derivatives

[0055] We studied the anti-tumor activity of Shikonin sugar derivatives of formul...

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PUM

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Abstract

The invention belongs to the field of chemical pharmaceutical technology, particularly relates to drug design of the traditional Chinese medicine extract shikonin serving as a lead compound and related research of anti-tumor activity. Carbohydrates are led into the framework molecule of the shikonin by means of chemical synthesis so as to obtain carbohydrate derivative with novel structure, and the research of in-vitro anti-tumor activity shows that the inhibition activity of the glycosyl shikonin on tumor cell A549 is obviously better than that of NCI-H460. From the activity result, the glycosyl shikonin can be prepared into anti-tumor medicament with high effect and low toxicity.

Description

1: Technical field [0001] The invention belongs to the technical field of chemical pharmacy, and specifically relates to the synthesis of a class of glycosyl shikonin and its application in tumor suppression. Two: background technology [0002] Shicaoning has broad-spectrum activity, and because of its obvious bactericidal activity, it was also used in daily necessities in the early days. Recent studies have shown that it plays an important role in anti-tumor as a topoisomerase inhibitor, and its application prospects and economic value are immeasurable. However, its potential toxic and side effects make it difficult to become a clinical candidate drug, and how to obtain corresponding high-efficiency and low-toxicity derivatives has become an important research topic. [0003] In order to obtain shikonin derivatives with low toxicity, many research groups have carried out derivative synthesis and corresponding activity research. YangFan is equal to SH-7, A NewSynthesized S...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18A61K31/7028A61P35/00
Inventor 杨永华王小明刘少华李鑫源刘昊琰赵卫国杨建文殷晶晶袁文勇圣丙刚
Owner NANJING UNIV
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