Beta-elemene 13-site derivative and use thereof in treatment of atherosclerosis

A technology of elemyl esters and compounds, applied in the fields of organic synthesis and medicinal chemistry, can solve the problems of no reports of antioxidant activity derivatives, low bioavailability, and single structural modification

Inactive Publication Date: 2014-11-05
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 β-elemene derivatives in the treatment of atherosclerosis. Therefore, by optimizing the structure of β-elemene, it is better to find new anti-oxidative damage effects than β-elemene The new compound has important significance for the treatment of atherosclerosis-related diseases
[0004] β-Elemene is a volatile oil, insoluble in water, with low bioavailability and moderate activity. In view of its structural characteristics, the research on its derivatization is very meaningful, and the previous research of scientific researchers mainly focused on the synthesis of β-elemene. The 13-position nitrogen-containing derivatives and ether derivatives of elemene have relatively simple structural modification, and no antioxidant active derivatives have been reported

Method used

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  • Beta-elemene 13-site derivative and use thereof in treatment of atherosclerosis
  • Beta-elemene 13-site derivative and use thereof in treatment of atherosclerosis
  • Beta-elemene 13-site derivative and use thereof in treatment of atherosclerosis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] The preparation method of intermediate 13-beta-elemenol (compound 1)

[0074] 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 3 times with dichloromethane, the combined dichloromethane was concentrated to obtain a light yellow liquid crude product, the liquid crude product was dissolved in 15 mL of anhydrous N,N-dimethylformamide (DMF), stirred Add 200mmol of anhydrous sodium acetate at 100°C for 7h. The reaction solution was suction-filtered with 200-mesh silica gel, and the filtrate was added with 15 mL of saturated saline, and extracted three times with petroleum ether. Concentrate petroleum ether to obtain a yellow liquid, which is dissolved in a mixed solution of 8 mL methanol and 8 mL chloroform, and 200 mmol potassi...

Embodiment 2

[0078] Preparation method of 4-(13-beta-elemenyloxy)-4-oxobutanoic acid (compound 2)

[0079] Dissolve 3mmol 13-β-elemenol in 10mL of anhydrous dichloromethane, add 0.3mmol 4-dimethylaminopyridine (DMAP), 0.3mmol 1-(3-dimethylaminopropyl)-3-ethyl carbon Diimine hydrochloride (EDCI) and 3.3 mmol succinic anhydride were reacted at room temperature for 10 h. 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 60%.

[0080] 1 H NMR (CDCl 3 ,300MHz)δ:1.01(s,3H),1.41-1.68(m,6H),1.71(s,3H),1.99-2.04(m,2H),2.64-2.74(m,4H),4.59(s, 1H), 4.62(s, 2H), 4.83(s, 1H), 4.88(s, 1H), 4.93(d, J=4.0Hz, 1H), 5.01(s, 1H), 5.05(s, 1H), 5.81(dd,J 1 =17.8Hz,J 2 =10.5Hz,1H).

[0081] 13 C NMR (CDCl 3 .

Embodiment 3

[0083] Preparation method of 5-(13-beta-elemenyloxy)-5-oxopentanoic acid (compound 3)

[0084] Dissolve 3mmol of 13-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 64%.

[0085] 1 H NMR (CDCl 3,300MHz)δ:1.01(s,3H),1.42-1.68(m,6H),1.71(s,3H),1.93-2.04(m,4H),2.45(t,J=7.2Hz,4H),4.60 (s,3H),4.83(s,1H),4.88(s,1H),4.92(d,J=4.1Hz,1H),5.01(s,1H),5.04(s,1H),5.81(dd, J 1 =17.8Hz,J 2 =10.4Hz,1H).

[0086] 13 C NMR (CDCl 3 .

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry, and in particular relates to a beta-elemene 13-site derivative (I) or (II), and R1 and R2 are as defined in specification. The invention also discloses a preparation method of the beta-elemene 13-site derivative and use thereof in anti atherosclerosis.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a class of β-elemene 13-position derivatives. The invention also discloses the preparation method of these β-elemene 13-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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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/40C07C69/42C07C69/83C07C69/145C07C69/24C07C69/587C07C69/78C07C69/767C07C69/92C07C201/12C07C205/57C07C69/618C07C69/65C07C69/88C07D213/80C07D213/79C07D307/68A61K31/455A61K31/4409A61K31/341A61K31/618A61K31/235A61K31/216A61K31/225A61K31/22A61K31/24A61P9/10
CPCA61K31/216A61K31/22A61K31/225A61K31/235A61K31/24A61K31/341A61K31/4409A61K31/455A61K31/618C07C67/08C07C69/145C07C69/24C07C69/40C07C69/42C07C69/587C07C69/618C07C69/65C07C69/78C07C69/88C07C69/92C07C201/12C07C205/57C07D213/79C07D213/80C07D307/68C07C2601/14C07C69/80C07C69/76
Inventor 尚靖徐进宜许海王若妍陈继超段文丽白仁仁
Owner DALIAN YUANDA PHARMA TECH DEV
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