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Alkannin acetyl glucose and preparation method and application thereof

A technology of shikonin and acetyl sugar, applied in the field of shikonin acetyl sugar and its preparation

Inactive Publication Date: 2010-03-17
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to find shikonin derivatives with better activity, we designed shikonin acetyl sugar derivatives, and found that this type of compound has better anti-tumor activity than shikonin, and has good drug resistance. And there is no literature report

Method used

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  • Alkannin acetyl glucose and preparation method and application thereof
  • Alkannin acetyl glucose and preparation method and application thereof
  • Alkannin acetyl glucose and preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0030] The reaction formula of the preparation method of the derivative of shikonin acetyl sugar is as follows:

[0031]

[0032] Aldose 1 (a~k) is acetylated under the action of acetic anhydride and sodium acetate, the acetic anhydride is 10 times the molar amount of 1, and the sodium acetate is the equimolar amount of 1, the reaction temperature is controlled at 80°C, and the reaction time is 4 hours , TLC tracking of the reaction process. After the reaction is completed, cool to room temperature, pour the reaction solution into an ice-cold saturated sodium bicarbonate solution to neutralize the remaining acetic anhydride, continue stirring for 1.5 hours, then add a suitable extractant for extraction, such as dichloromethane, etc., and purify by column chromatography. The peracetyl sugars 2(a~k) were obtained.

[0033] Peracetylsugar 2 (a~e, i~k) was then reacted with hydrazine acetate at room temperature for 4 hours, tetrahydrofuran was used as a solvent, and the amount...

Embodiment 1

[0043] 1-(1-(5,8-dihydroxy-1,4-naphthoquinone-2-yl)-4-methyl-3-pentyl)-2,3,4,6-tetra-O-acetyl -β-D-glucopyranose

[0044] Add 1.80g (10mmol) of glucose and 1.07g (13mmol) of anhydrous sodium acetate into a single-necked flask, add 9.4mL (100mmol) of acetic anhydride, control the reaction temperature at 80-90°C, and the reaction time is about 4 hours. TLC tracking. After the reaction is completed, cool to room temperature, pour the reaction solution into ice-cold saturated sodium bicarbonate solution, neutralize the remaining acetic anhydride, continue to stir for 1.5 hours, then add a suitable extractant for extraction, such as dichloromethane, etc., then separate and pass Purified by column chromatography to obtain 3.62 g (92.8% yield) of 1,2,3,4,6-penta-O-acetylglucose.

[0045] Dissolve 1.95 g (5 mmol) of pentaacetylglucose in 20 mL of tetrahydrofuran, add 0.506 g (5.5 mmol) of hydrazine acetate and stir at room temperature for 4 hours. After the reaction, tetrahydrofuran ...

Embodiment 2

[0051] 1-(1-(5,8-dihydroxy-1,4-naphthoquinone-2-yl)-4-methyl-3-pentyl)-2,3,4,6-tetra-O-acetyl -β-D-mannopyranose

[0052] The operation was the same as in Example 1, except that glucose was replaced by mannose to obtain the title compound with the following structure.

[0053] 1 H NMR (400MHz, CDCl 3 ): δ12.57(s, 1H), 12.46(s, 1H), 7.18(m, 3H), 5.30(m, 2H), 5.23(t, J=10Hz, 1H), 5.12(t, J=6.8 Hz, 1H), 5.04(m, 2H), 4.14(dd, J=5.6, 12.0Hz, 1H), 3.89(dd, J=1.6, 12.4Hz, 1H), 3.83(m, 1H), 2.51(m , 1H), 2.45(m, 1H), 2.14(s, 3H), 2.02(s, 3H), 2.00(s, 3H), 1.94(s, 3H), 1.67(s, 3H), 1.58(s, 3H) ppm;

[0054] 13 C NMR (100MHz, CDCl 3 ): δ177.9, 176.4, 170.4, 169.9, 169.7, 169.7, 167.8, 167.3, 148.9, 136.6, 133.1, 132.7, 132.1, 117.4, 111.7, 111.5, 97.5, 73.2, 69.4, 69.3, 68.9, 2 33.5, 25.7, 20.8, 20.7, 20.6, 20.4, 18.0ppm;

[0055]

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Abstract

The invention discloses alkannin acetyl glucose and a preparation method and an application thereof. The method comprises the following steps: adding 1 mol of 1- trichloroacetamido-acetyl glucose and 1-2 mol of alkannin into dichloromethane solution, and reacting at the temperature of minus 20-minus 40 DEG C under the existence of 4angstrom of molecular sieve and boron trifluoride diethyl etherate, thus obtaining alkannin acetyl glucose. The alkannin acetyl glucose is used for the medicines with tumor activity resistance and drug resistance. In the invention, the alkannin acetyl glucose is prepared simply and effectively by four steps of reaction, the tumor activity resistance and drug resistance of the alkannin acetyl glucose are inspected, therefore, the alkannin acetyl glucose which has strong inhibiting action to the tumor cell lines is showed, and the good drug resistance of the alkannin acetyl glucose are also proved, and the alkannin acetyl glucose is a prospecting medicine for resisting tumor.

Description

technical field [0001] The present invention relates to a compound and its preparation method, in particular to a shikonin acetyl sugar, its preparation method and application. Background technique [0002] 5,8-Dihydronaphthoquinone compounds have been identified by the National Cancer Institute of the United States as substances with antitumor activity, and shikonin (SH) is a typical representative of such compounds. Shikonin has a wide range of biological activities including: antibacterial, anti-AIDS, promotion of burn wound healing, anti-tumor, etc., which has attracted the attention of researchers. In recent years, the research on shikonin has mainly focused on the following aspects: the research on the new pharmacodynamics of shikonin, the total synthesis of shikonin and the modification and derivatization of shikonin. [0003] [0004] Weak antitumor activity and poor water solubility prevent shikonin from being a good antitumor drug. For this reason, many researc...

Claims

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Application Information

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IPC IPC(8): C07H15/18C07H1/00A61K31/7032A61P35/00
Inventor 王彦广苏叶华谢建胜胡汛
Owner ZHEJIANG UNIV
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