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Curcumin-amino acid conjugate and application

A technology of amino acids and conjugates, which is applied in the application field of curcumin-amino acid binary conjugates in the preparation of anti-inflammatory drugs, and can solve problems such as complex processes

Active Publication Date: 2016-07-27
INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] To sum up, most of the conventional curcumin structural modification is esterification on the phenolic hydroxyl group, which needs to be protected by amino acid protection groups before structural modification, and finally deprotection, which involves multi-step chemical reactions and complicated processes

Method used

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  • Curcumin-amino acid conjugate and application

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Experimental program
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Effect test

Embodiment 1

[0070] The preparation of embodiment 1 curcumin

[0071] Take 60g of vanillin and 210mL of tributyl borate, add it to 200mL of dry ethyl acetate, stir and mix; then add 20g of acetylacetone and 10g of boric anhydride, stir at room temperature for 10min, then add dropwise 1-n-butylamine to catalyze the reaction, and stir at room temperature When the reaction is complete, add 300mL of dilute hydrochloric acid aqueous solution, stir at 60°C for 60min, separate the ethyl acetate layer, concentrate, add an appropriate amount of methanol to precipitate the product, leave it at -4°C, filter, and dry in vacuo to obtain 43.5g of yellow curcumin solids, Yield 62% (synthetic route sees figure 1 , see the characterization map Figure 2-4 ).

Embodiment 2

[0072] The preparation of embodiment 2 curcumin-glycine conjugates

[0073] Take 0.68g (9.0mmol) glycine and 0.76g sodium bicarbonate (9.0mmol), dissolve in 6mL deionized water, add 1.5mL aqueous formaldehyde (37%, 18.0mmol), stir at room temperature for 2 hours, then add 50mL methanol to dilute Above-mentioned reaction solution, then add 1.11g (3.0mmol) curcumin, stir reaction at room temperature for 2 hours, TLC monitors to curcumin reaction completely, add dropwise appropriate amount of 0.5M dilute hydrochloric acid to neutralize sodium bicarbonate, reaction product uses silica gel column chromatography Separation, dichloromethane / methanol / glacial acetic acid mixed solvent elution, obtain curcumin-glycine conjugate 0.89g, yield 43.2% (synthetic route sees Figure 5 ).

Embodiment 3

[0074] The preparation of embodiment 3 curcumin-alanine conjugates

[0075] Take 0.81g (9.0mmol) alanine and 0.76g sodium bicarbonate (9.0mmol), dissolve in 6mL deionized water, add 1.5mL formaldehyde aqueous solution (37%, 18.0mmol), stir at room temperature for 2 hours, then add 50mL Dilute the above-mentioned reaction solution with methanol, then add 1.11g (3.0mmol) curcumin, stir and react at room temperature for 3 hours, TLC monitors until the curcumin reaction is complete, add dropwise an appropriate amount of 0.5M dilute hydrochloric acid to neutralize sodium bicarbonate, and the reaction product is purified by silica gel column Chromatographic separation, dichloromethane / methanol / glacial acetic acid mixed solvent elution, to obtain curcumin-alanine conjugate 0.98g, yield 44.8% (synthetic route sees Image 6 ).

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Abstract

The invention discloses curcumin-amino acid conjugate and application.The curcumin-amino acid conjugate has the following structure (please see the structure in the description).Experiments show that the curcumin-amino acid conjugate can obviously reduce release of mouse mononuclear macrophage RAW264.7 inflammation model NO induced by lipopolysaccharide, and the curcumin-amino acid conjugate shows an excellent inflammation resisting effect, has the advantages of being simple in preparation method, low in production cost, high in inflammation resisting activity, low in toxicity, easy to dissolve in water and high in bioavailability, and has great potential value in the aspect of anti-inflammatory drug development.

Description

technical field [0001] The invention belongs to the field of organic synthesis and medicine, in particular to a curcumin-amino acid conjugate for treating inflammatory diseases and its application, in particular to the application of curcumin-amino acid binary conjugate in the preparation of anti-inflammatory drugs . Background technique [0002] Curcumin (Curcumin, chemical name: 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) is derived from Curcuma longa, Curcuma longa A polyphenolic compound (chemical structure shown in formula A) extracted and separated from the dried rhizomes of gold and curcuma, has a wide range of pharmacological effects such as anti-inflammatory, anti-oxidation, anti-tumor, blood lipid regulation, and anti-fibrosis. For the treatment of tumors, diabetes, AIDS, rheumatoid arthritis, atherosclerosis and other clinical diseases [1-7] . A large number of scientific studies have confirmed that curcumin has varying degrees of inhibitory ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/16C07D207/16C07D413/14C07D403/14A61K47/48A61P29/00A61P19/02A61P11/00A61P1/16A61P1/18A61P1/00
CPCC07D207/16C07D265/16C07D403/14C07D413/14
Inventor 刘天军朱纪林刘娟洪阁
Owner INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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