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Shikonin octyl methoxycinnamate derivant as well as synthesis method and application thereof

A technology of cinnamate esters and derivatives is applied in the field of preparation and application in tumor suppression, and can solve problems such as changing the related properties of shikonin

Inactive Publication Date: 2012-07-04
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to its obvious fat-soluble characteristics, various problems will be encountered in the application process. Therefore, we hope to introduce different cinnamic acid ester derivatives into the structure of shikonin to change the related properties of shikonin, and then solve the molecular problem. Disadvantages of its own

Method used

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  • Shikonin octyl methoxycinnamate derivant as well as synthesis method and application thereof
  • Shikonin octyl methoxycinnamate derivant as well as synthesis method and application thereof
  • Shikonin octyl methoxycinnamate derivant as well as synthesis method and application thereof

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Effect test

example 1

[0037] Example 1: Synthetic method of formula I class shikonin cinnamate derivatives

[0038]Dissolve 50mmol of shikonin and 50mmol of the corresponding cinnamic acid in 20mL of refined dichloromethane, and continue to add a catalytic amount of N,N-dicyclohexylcarbodiimide (DCC) and 4 - Dimethylaminopyridine (DMAP), TLC follow-up detection to generate corresponding ester derivatives. Add an appropriate amount of silica gel to concentrate the solvent under reduced pressure, and perform column chromatography with ethyl acetate:petroleum ether=1:7 to obtain the corresponding shikonin carboxylate derivatives.

[0039] The reaction takes the synthesis of 2,4-dichlorocinnamic acid shikonin as an example:

[0040]

[0041] Compound 1

[0042] Compounds 2-21 can be obtained in the same way.

[0043]

[0044] The physicochemical data of the corresponding compounds are as follows:

[0045] Compound 1: 1 H NMR (500MHz, CDCl 3 )δ: 12.646 (s, 1H, -OH); 12.458 (s, 1H, -OH); 7.76...

example 2

[0064] Example 2. Application of Formula I Class Shikonin Cinnamate Derivatives

[0065] We studied the anti-tumor activity of Shikonin cinnamic acid derivatives of formula I, selected tumor cells A875, SW872-S and A549 as detection cells, measured their absorbance at 570nm with a microplate reader by MTT method and calculated OD value.

[0066] IC 50 The value calculation method is as shown in the formula:

[0067] Cell inhibition rate (%)=(OD value of control group-OD value of experimental group) / OD value of control group×100%

[0068] The results show that most of the shikonin cinnamate derivatives have very good inhibitory effect on anti-tumor activity. The corresponding results are attached Figure 1-3 .

[0069] The results of the activity of the three cell lines showed that the derivatives of shikonin cinnamate had obvious inhibitory activity on the cancer cell lines A875, SW872-S and A549, and the compound with the best activity was 3,4-difluorocinnamic acid shiko...

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Abstract

The invention belongs to the technical field of the chemical pharmacy, in particular to medicine design which takes shikonin as a primer and a relevant research for antitumor activity. A series of substituted cinnamic acid is introduced into a shikonin skeleton molecule by a synthesis means to obtain a corresponding ester derivant. The in-vitro antitumor activity research shows that the shikonin octyl methoxycinnamate derivant has strong inhibitory activity on tumor cell strains.

Description

1: Technical field [0001] The invention belongs to the technical field of chemical pharmacy, and in particular relates to the preparation of a class of shikonin cinnamate derivatives and their 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 is an anti-tumor functional molecule with great potential. However, due to its obvious fat-soluble characteristics, various problems will be encountered in the application process. Therefore, we hope to introduce different cinnamic acid ester derivatives into the structure of shikonin to change the related properties of shikonin, and then solve the molecular problem. inherent disadvantages. [0003] Check relevant literature and find that this class of compounds is first seen in Antimicrobial Activities of Naphthazarins from Arnebia euch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/618C07C69/65C07C69/734C07C67/08A61K31/216A61P35/00
Inventor 杨永华王小明林红燕石婧刘洪昌孔文尧浩日沁巴图黄守程
Owner NANJING UNIV
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