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Lys(Pro-Ala-Lys) curcumin derivatives, synthesis thereof and application thereof in medical science

A technology of drugs and anti-inflammatory drugs, applied in the field of biomedicine, can solve the problem that curcumin does not have thrombolytic activity and other problems

Inactive Publication Date: 2015-05-13
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although curcumin has shown expected activity in the in vitro anti-platelet aggregation model, in vitro free radical scavenging model, rat arteriovenous bypass cannulation antithrombotic model and mouse ear swelling anti-inflammatory model, and these activities have no effect on cerebral ischemia Reperfusion injury, myocardial ischemia-reperfusion injury, and lung reperfusion injury all have protective effects, but curcumin has no thrombolytic activity, that is, the prerequisite for ischemia-reperfusion does not exist

Method used

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  • Lys(Pro-Ala-Lys) curcumin derivatives, synthesis thereof and application thereof in medical science
  • Lys(Pro-Ala-Lys) curcumin derivatives, synthesis thereof and application thereof in medical science
  • Lys(Pro-Ala-Lys) curcumin derivatives, synthesis thereof and application thereof in medical science

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1 prepares Boc-Pro-Ala-Lys (Boc)

[0034] 1) Preparation of Boc-Pro-Ala

[0035] 1.075g (5.0mmol) of Boc-Pro was dissolved in 20mL of anhydrous THF, and 0.637g (5mmol) of N-hydroxysuccinimide (HOSu) was added to the solution under ice cooling, and completely dissolved. Under ice-cooling, 1.236 g (6.0 mmol) of dicyclohexylcarbodiimide (DCC) dissolved in a small amount of anhydrous THF was added to the reaction solution. Stir at room temperature for 7 h, and monitor the disappearance of Boc-Pro by TLC (petroleum ether / ethyl acetate, 3:1). Dicyclohexylurea (DCU) was filtered off, and the filtrate was concentrated under reduced pressure to remove THF. The residue was dissolved with ethyl acetate, and the solution was successively washed with saturated NaHCO 3 After washing with aqueous solution and saturated NaCl aqueous solution, the ethyl acetate layer was concentrated to dryness under reduced pressure, the residue was dissolved by adding an appropriate amou...

Embodiment 2

[0040] Example 2 Preparation of 1-(3-methoxy-4-hydroxyphenyl)-7-[(4-oxoacetoxy)-3-methoxyphenyl]-1,6-heptadiene-3, 5-diketone

[0041] 1) Preparation of 6-(3-methoxy-4-hydroxyphenyl)-5,6-hexene-2,4-dione

[0042] Put 31mL (0.3mol) of acetylacetone in a 250mL three-neck flask, add 14.5g (0.21mol) of boron trioxide and 70mL of ethyl acetate, react at 70°C for one hour to turn into a white suspension, then add 29.5mL ( 0.11mol) tri-n-butyl borate and 15.2g (0.1mol) 3-methoxy-4-hydroxybenzaldehyde, react at 85°C for 0.5 hours to make the solution a light yellow suspension, add 10.88mL (0.11 mol) ethyl acetate solution of n-butylamine, react for 1 hour to make the solution turn red, cool down to 50°C, add 200mL 1N hydrochloric acid, react for 0.5 hour, stop the reaction. The aqueous layer was separated, extracted three times with 40 mL ethyl acetate, combined ethyl acetate, dried with anhydrous sodium sulfate, filtered off sodium sulfate, the filtrate was desolvated under reduced...

Embodiment 3

[0048] Example 3 Preparation of 1-(3,4-di-methoxyphenyl)-7-[(4-oxoacetoxy)-3-methoxyphenyl]-1,6-heptadiene-3,5 - dione

[0049] 1) Preparation of 6-(3,4-di-methoxyphenyl)-5,6-hexene-2,4-dione

[0050] According to the preparation method of item 1) in Example 2, 16.6g (0.1mol) 3,4-di-methoxybenzaldehyde and 31mL (0.3mol) acetylacetone were reacted to obtain 8.6g (34.6% ) the title compound as a pale yellow solid. ESI-MS(m / e): 235[M+H] + .

[0051] 2) 1-(3,4-di-methoxyphenyl)-7-(4-oxoacetylethyl-3-methoxyphenyl)-1,6-heptadiene-3,5-dione preparation of

[0052] According to the preparation method of item 1) in Example 2, by 1.097g (4.42mmol) 6-(3,4-di-methoxyphenyl)-5,6-hexene-2,4-diketone and 1.088g ( 4.87 mmol) of 3-methoxy-4-oxoacetoethoxybenzaldehyde was reacted and purified by silica gel column chromatography to obtain 0.435 g (21.0%) of the title compound as a pale yellow solid. ESI-MS(m / e): 469.6[M+H] + .

[0053] 3) 1-(3,4-di-methoxyphenyl)-7-(4-oxoacetoxy-3-meth...

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Abstract

The invention discloses pseudopeptides with a formula as the following. The invention further discloses a preparation method and an application of the pseudopeptides. The pseudopeptides provided by the invention have excellent thrombolytic activities, antithrombotic activities, anti-inflammatory activities, OH free radical scavenging activities and nanostructures.

Description

[0001] This application is filed on December 14, 2011. The application number is: 201110415171.7, and the invention title is "Lys and Lys (Pro-Ala-Lys) modified curcumin derivatives, their synthesis and application in medicine". Divisional application. technical field [0002] The present invention relates to pseudopeptides of the following formula, and further relates to their preparation methods and uses. The compound of the present invention has excellent thrombolytic activity, antithrombotic activity, anti-inflammatory activity, OH free radical scavenging activity and nanometer structure. The invention belongs to the field of biomedicine. [0003] Background technique [0004] Curcumin is one of the active ingredients of turmeric. It has antithrombotic, anti-inflammatory and free radical scavenging activities. It is a safe and low-toxic natural product. The inflammatory response promotes the release of coagulation factors and platelet activation, while down-regulati...

Claims

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Application Information

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IPC IPC(8): C07K5/11A61K38/07A61P29/00A61P39/06A61P7/02
Inventor 赵明彭师奇王玉记吴建辉王枫
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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