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Amphipathic compound of curcumin derivates and polyoxyethylene as well as preparation method and application thereof

A technology of polyoxyethylene and compounds, applied in the direction of drug combination, digestive system, pharmaceutical formula, etc., can solve problems such as inability to achieve good water solubility, good biocompatibility, and significant clinical application value

Inactive Publication Date: 2011-07-27
唐华东
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is also limited by the water solubility and poor stability of the aforementioned curcumin, so it cannot be practically used in clinical practice.

Method used

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  • Amphipathic compound of curcumin derivates and polyoxyethylene as well as preparation method and application thereof
  • Amphipathic compound of curcumin derivates and polyoxyethylene as well as preparation method and application thereof
  • Amphipathic compound of curcumin derivates and polyoxyethylene as well as preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0057] The present invention also provides a preparation method of the compound, preferably taking curcumin and short-chain polyoxyethylene as examples. Its preparation process comprises the following two simple steps: (1) β-mercaptopropionic acid reacts with curcumin to generate curcumin with thiol end as shown in formula II; (2) curcumin with mercapto end and monomethoxy Polyoxyethylene acrylate undergoes Michael addition reaction to generate the amphiphilic curcumin compound shown in formula I. Compared with other preparation methods of curcumin derivatives, the method has fewer steps, high yield, low cost, easy-to-obtain raw materials, simple process and is suitable for industrialized production.

[0058] Specifically, in step (1), dry tetrahydrofuran, acetone, chloroform, N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, etc. are used as solvents, preferably tetrahydrofuran or acetone, mix β-mercaptopropionic acid and N, N-dicyclohexylcarbodiimide with a mo...

Embodiment 1

[0062] Embodiment 1. the synthesis of curcumin with sulfhydryl end

[0063] 1.1g β-mercaptopropionic acid and 2.2g N, N-dicyclohexylcarbodiimide were dissolved in 50mL of dry tetrahydrofuran, after stirring, 1.9g curcumin and 0.06g 4-dimethylaminopyridine were added, and the solution was After stirring at room temperature for 12 hours, filter, add 100 mL of n-hexane to the filtrate, collect the precipitate by centrifugation, wash the precipitate with ether, and dry it under vacuum at room temperature to obtain 2.6 g of curcumin with a mercapto end shown in formula II, with a yield of 92%.

[0064] The synthesis of amphiphilic curcumin-polyoxyethylene compound shown in embodiment 2. formula I

[0065] 5.4 g of curcumin with mercapto end, 10.0 g of monomethoxypolyoxyethylene acrylate (Mn=500) and 0.02 g of triethylamine were dissolved in 100 mL of dry tetrahydrofuran, and after stirring at room temperature for 12 hours, 200 mL of the solution was added. Dry the ether, centrifug...

Embodiment 2

[0067] The compound obtained in Example 2 is an orange to brown-yellow viscous liquid at room temperature, has a water solubility greater than 50 mg / mL, and is stable for half a year when stored at room temperature. This compound is carried out HPLC detection (BeckmanSystem Gold, Luna C18 5 μ 4.6 * 250mm column, mobile phase: methanol: water=85: 15), the result is as follows figure 1 shown. figure 1 It shows that the compound has a high purity, and the purity is greater than 98% according to the integral area. With deuterated chloroform as solvent, the compound 1H-NMR results are (Bruker AdvanceDRX-400): 7.6ppm (d), 7.1ppm (m), 6.6ppm (d), 5.8ppm (b), 4.2ppm (s) , 3.9ppm(s), 3.7ppm(s), 3.3ppm(s), 2.9ppm(m), 2.7ppm(m).

[0068] The performance of amphiphilic curcumin-polyoxyethylene compound shown in embodiment 4. formula I

[0069] The compound obtained by weighing 1.0g embodiment 2 was dissolved in 1L of water, stirred at room temperature for 10 minutes to form micelles or...

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Abstract

The invention relates to an amphipathic compound of curcumin derivates and polyoxyethylene as well as a preparation method thereof, wherein PEO is polyoxyethylene, and R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 which are independently selected from hydrogen atom, hydroxide radical, phenyl, linear chain or branched chain alkyl group, linear chain or branched chain alkoxy, amidogen, mono-alkylation amidogen, dialkyl amine amidogen, halogen and halogenate alkyl group. The compound has the advantages of good compound stability, good water-solubility, good biocompatibility, low toxic and side effects, high bioavailability, low production cost and the like, and is easy to inject and administrate and the preparation process is simple. In addition, the invention also relates to an application ofthe amphipathic compound of curcumin derivates and polyoxyethylene in preparing the medicaments for resisting fatty liver, hepatic fibrosis and cirrhosis. The amphipathic compound has obvious pharmacology activity of resisting inflammation and hepatic fibrosis, delaying the forming of cirrhosis and reducing blood fat.

Description

technical field [0001] The technical field of the present invention is the field of medicinal chemistry, and relates to an amphiphilic compound formed by combining curcumin derivatives with polyoxyethylene and a preparation method thereof, and the amphiphilic compound is used in the preparation of anti-hepatic fibrosis, anti-fatty liver, anti- Applications in liver cirrhosis drugs and drugs for the treatment of triglycerides. Background technique [0002] Curcumin is a polyphenolic compound extracted from the rhizomes of turmeric plants such as turmeric, turmeric, and zedoary. It has anti-inflammatory, anti-oxidation, anti-mutagenic and other pharmacological activities. It can inhibit aging, resist tumors, and lower blood lipids. Curcumin is a food additive widely used in Southeast Asian countries. It has a wide range of sources, low price, and various curative effects (Mai Zhenjiang. Research progress in the pharmacological effects of curcumin. Chinese Materia Medica, 2004,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/00A61K9/00A61K9/12A61K9/70A61K47/48A61P1/16A61P3/06A61K31/795A61K47/60
Inventor 唐华东
Owner 唐华东
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