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Beta-elemene 14-site ramification and application of beta-elemene 14-site ramification in treating atherosclerosis

A kind of technology of elemenol ester and compound, which is applied in the field of preparation of β-elemene 14-position derivatives and β-elemene 14-position derivatives

Inactive Publication Date: 2014-10-29
DALIAN YUANDA PHARMA TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the research on β-elemene derivatives in the treatment of atherosclerosis. Therefore, by optimizing the structure of β-elemene, looking for new lead compounds with obvious anti-oxidative damage effects on the treatment of arteriosclerosis Atherosclerosis-related diseases have important implications

Method used

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  • Beta-elemene 14-site ramification and application of beta-elemene 14-site ramification in treating atherosclerosis
  • Beta-elemene 14-site ramification and application of beta-elemene 14-site ramification in treating atherosclerosis
  • Beta-elemene 14-site ramification and application of beta-elemene 14-site ramification in treating atherosclerosis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] The preparation method of intermediate 14-beta-elemenol (compound 1)

[0075] Dissolve 100mmol of β-elemene in 20mL of dichloromethane and acetic acid mixed solution (V:V=2:1), slowly drop into sodium hypochlorite solution containing 180mmol of active chlorine in ice bath, and react in ice bath for 4h. The dichloromethane layer was separated, the aqueous layer was extracted three times with dichloromethane, the combined dichloromethane was concentrated to obtain a light yellow liquid crude product, without further purification, the liquid crude product was dissolved in 15 mL of anhydrous N,N-dimethylformaldehyde Add 200mmol of anhydrous sodium acetate under stirring to amide (DMF), and react at 100°C for 7h. The reaction solution was suction-filtered with diatomaceous earth, and the filtrate was added with 15 mL of saturated brine, and extracted three times with petroleum ether. The petroleum ether was concentrated to obtain a yellow liquid, which was separated by colu...

Embodiment 2

[0079] Preparation method of 4-(14-beta-elemeneoxy)-4-oxobutanoic acid (compound 2)

[0080] Dissolve 3mmol of 14-β-elemenol in 10mL of anhydrous dichloromethane, add 0.3mmol of DMAP, 0.3mmol of EDCI and 3.3mmol of succinic anhydride, and react at room temperature for 10h. The reaction solution was washed three times with 10% hydrochloric acid, and the dichloromethane layer was concentrated to obtain a pale yellow liquid. Column chromatography with petroleum ether: ethyl acetate = 8:1 (V:V) gave a colorless liquid product with a yield of 67%.

[0081] 1 H NMR (CDCl 3 ,300MHz)δ:0.99(s,3H),1.40-1.65(m,6H),1.74(s,3H),1.92-1.97(m,1H),2.01-2.06(m,1H),2.63-2.73( m,4H),4.51(s,2H),4.72(s,2H),4.89-4.95(m,3H),5.13(s,1H),5.75(dd,J 1 =17.8Hz,J 2 =10.4Hz,1H).

[0082]13 C NMR (CDCl 3 ,300MHz)δ:177.9,171.7,150.0,149.3,145.9,113.6,111.0,108.4,68.6,48.3,45.6,39.7,33.0,28.9,26.7,21.0,16.0.

Embodiment 3

[0084] Preparation method of 5-(14-beta-elemenyloxy)-5-oxopentanoic acid (compound 3)

[0085] Dissolve 3mmol of 14-β-elemenol in 10mL of anhydrous dichloromethane, add 0.3mmol of DMAP, 0.3mmol of EDCI and 3.3mmol of glutaric anhydride, and react at room temperature for 10h. The reaction solution was washed three times with 10% hydrochloric acid, and the dichloromethane layer was concentrated to obtain a light yellow liquid. Column chromatography with petroleum ether: ethyl acetate = 8:1 (V:V) gave a colorless liquid product with a yield of 74%.

[0086] 1 H NMR (CDCl 3 ,300MHz)δ:1.00(s,3H),1.41-1.65(m,6H),1.74(s,3H),1.92-2.06(m,4H),2.44(t,J=7.3Hz,4H),4.49 (s,2H),4.71(s,2H),4.88(s,1H),4.90(d,J=4.7Hz,1H),4.95(s,1H),5.13(s,1H),5.75(dd, J 1 =17.8Hz,J 2 =10.4Hz,1H).

[0087] 13 C NMR (CDCl 3 .

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry, and particularly relates to a beta-elemene 14-site ramification (I) or (II), wherein R1 and R2 are defined in the specification. The invention also discloses a preparation method of the beta-elemene 14-site ramification and application of the beta-elemene 14-site ramification on the aspect of resisting atherosclerosis. The ramifications I and II are as shown in the specification.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a class of β-elemene 14-position derivatives. The invention also discloses the preparation method of these β-elemene 14-position derivatives and their anti-atherogenic properties. applications in sclerosis. Background technique [0002] Cardiovascular and cerebrovascular diseases, including coronary artery disease and stroke, are the main fatal diseases in the world. In recent years, with the continuous improvement of people's living standards and changes in eating habits, the incidence rate has been increasing year by year. It is reported that 100 million people per year Sixty-seven million people died of cardiovascular disease. AS is the common pathophysiological basis of cardiovascular and cerebrovascular events and an important factor causing cardiovascular and cerebrovascular diseases and death. In recent years, studies have shown that the occurrenc...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/145C07C69/24C07C69/587C07C69/78C07C69/92C07C69/618C07C69/65C07C69/84C07C69/40C07C69/83C07C69/42C07D213/80C07D213/803C07D213/79C07D307/68A61K31/225A61K31/235A61K31/22A61K31/24A61K31/216A61K31/4406A61K31/4409A61K31/341A61P9/10
CPCA61K31/216A61K31/22A61K31/225A61K31/235A61K31/24A61K31/341A61K31/4406A61K31/4409C07C67/08C07C69/145C07C69/24C07C69/40C07C69/42C07C69/587C07C69/618C07C69/65C07C69/78C07C69/84C07C69/92C07D213/79C07D213/80C07D213/803C07D307/68C07C69/80C07C2601/14
Inventor 尚靖徐进宜许海王若妍段文丽陈继超白仁仁
Owner DALIAN YUANDA PHARMA TECH DEV
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