Beta-elemene monosubstituted ether derivatives, synthesis method and use thereof

An elemene mono- and synthetic method technology, which is applied in the directions of drug combination, ether/acetal active ingredients, ether preparation, etc., can solve problems such as unfavorable ethers, and achieves the promotion of production, good water solubility, and high anticancer activity Effect

Inactive Publication Date: 2008-04-23
SHANGHAI INST OF APPLIED PHYSICS - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction is carried out under the condition of water, which is not conducive to the formation of ether

Method used

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  • Beta-elemene monosubstituted ether derivatives, synthesis method and use thereof
  • Beta-elemene monosubstituted ether derivatives, synthesis method and use thereof
  • Beta-elemene monosubstituted ether derivatives, synthesis method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～24

[0028] Embodiment 1~24β-elemene monosubstituted ether derivatives

[0029] Examples 1-24 of β-elemene monosubstituted ether derivatives whose specific structure is A or B in formula I are given in Table 1.

[0030]

[0031] Formula I

[0032] Table 1 β-elemene monosubstituted ether derivatives Examples 1-24

[0033] Example

specific structure

R 1

Example

specific structure

R 2

1

A

-CH 3

13

B

-CH 3

2

A

-CH 2 CH 3

14

B

-CH 2 CH 3

3

A

-(CH 2 ) 5 CH 3

15

B

-(CH 2 ) 5 CH 3

4

A

-(CH 2 ) 10 CH 3

16

B

-(CH 2 ) 10 CH 3

5

A

-CH 2 CH 2 OCH 3

17

B

-CH 2 CH 2 OCH 3

6

A

-(CH 2 CH 2 O) 7 CH 3

18

B

-(CH 2 CH 2 O) 7 CH 3

7

A

-(CH 2 CH 2 O) 16 CH 3

19

...

Embodiment 1

[0039] Synthesis of method embodiment 1β-elemene monosubstituted methyl ether

[0040]

[0041] The β-elemene chloride mixture was dissolved in methanol, and the molar ratio of β-elemene chloride to methanol was 1:20. Then add the basic catalyst KOH, and the molar ratio of β-elemene chloride to KOH is 1:5. The reactants were reacted at 40°C for 1 hour under reflux to obtain the product β-elemene monosubstituted methyl ether. The NMR characterization results are as follows:

[0042] 1 H-NMR (CDCl 3 , TMS, 500MHz), δ(ppm): 0.94(s, 3H), 1.36-1.71(m, 6H), 1.64(s, 3H), 1.94-2.00(m, 2H), 3.24(s, 3H), 3.84(s, 2H), 4.52(s, 1H), 4.75(s, 1H), 4.81(s, 1H), 4.84(d, J=3.46, 1H), 4.90(s, 1H), 4.956(s, 1H), 5.74 (dd, J=11.20, 6.47, 1H).

Embodiment 2

[0043] Synthesis of method embodiment 2β-elemene monosubstituted ethyl ether

[0044]

[0045] The β-elemene chloride mixture is dissolved in ethanol, and the molar ratio of β-elemene chloride to ethanol is 1:15. Then add the basic catalyst Na 2 CO 3 , β-elemene chloride and Na 2 CO 3 The molar ratio is 1:6. The reactants were reacted at 40°C for 25 hours under reflux to obtain the product β-elemene monosubstituted ethyl ether, and the characterization results were as follows:

[0046] Infrared Characterization: IR V max : 3081, 1639, 1454, 1441, 1105, 905, 889.

[0047] NMR characterization: 1 H-NMR (CDCl 3 , TMS, 500MHz), δ (ppm): 0.94 (s, 3H), 1.15 (t, J=7.01, 3H), 1.36-1.44 (m, 3H), 1.49-1.62 (m, 3H), 1.94-2.08 (m, 2H), 3.40(q, J=6.97, 2H), 3.89(s, 2H), 4.52(s, 1H), 4.75(s, 1H), 4.82(s, 1H), 4.85(d, J = 6.37, 1H), 4.89 (s, 1H), 4.96 (s, 1H), 5.75 (dd, J = 17.36, 11.04, 1H).

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Abstract

The present invention discloses monosubstituted beta-elemene ether derivative as shown and its pharmaceutically acceptable salt. The present invention also discloses the synthesis process and application in preparing anticancer medicine of the monosubstituted beta-elemene ether derivative. The monosubstituted beta-elemene ether derivative of the present invention has high water solubility, high anticancer activity, no toxicity, high medicine effect and high bioavailability.

Description

technical field [0001] The invention relates to a novel compound β-elemene monosubstituted ether derivative, its synthesis method and application in the field of medicine. Background technique [0002] Cancer is a common disease that seriously endangers people's life and health at present. β-Elemene is the first anti-cancer active ingredient extracted from the rhizome of Zingiberaceae Wen Curcuma (Wen Curcuma) in my country in recent years. Its molecular formula is C 15 h 24 , the structural formula is as follows: [0003] [0004] β-Elemene has been used clinically as a traditional Chinese medicine, but its clinical application is limited due to its extremely poor water solubility. Therefore, how to improve its water solubility has been attracting much attention. In the prior art, the main work is to improve water solubility by synthesizing β-elemene derivatives. [0005] Jia Weimin Shen Jing conducted a systematic study on the structure-activity relationship of β-ele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/162C07C43/168C07C41/01A61K31/075A61P35/00
Inventor 沈玉梅刘贵峰成康民王谋华孙艳红任云峰冯翠兰
Owner SHANGHAI INST OF APPLIED PHYSICS - CHINESE ACAD OF SCI
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