Cholic acid-modified glucosamine derivative and preparation method and application thereof

A technology of glucosamine and derivatives, which is applied in the field of bile acid modified glucosamine derivatives and its preparation, achieves the effects of high yield, convenient operation and unique biological activity

Inactive Publication Date: 2015-10-07
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention proposes a method of modifying glucosamine with cholic acid to solve the problems existing in existing drugs for treating osteoarthritis and cartilage repair materials

Method used

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  • Cholic acid-modified glucosamine derivative and preparation method and application thereof
  • Cholic acid-modified glucosamine derivative and preparation method and application thereof
  • Cholic acid-modified glucosamine derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of derivatives without polymerizable groups: cholic acid modified glucosamine derivatives, comprising the steps of:

[0036] Add 4.0858g (0.01mol) of cholic acid and 1.1509g (0.01mol) of N-hydroxysuccinimide into a 150ml three-necked flask, stir and dissolve in 30ml of tetrahydrofuran, and slowly add 3.0949g (0.015mol) of N , N'-dicyclohexylcarbodiimide in 10ml tetrahydrofuran solution, keep warm for 2h, return to room temperature, continue the reaction for 18h, then stop the reaction, filter the filtrate, and remove the solvent by rotary evaporation. Purified by silica gel column chromatography, the eluent was petroleum ether / ethyl acetate (1 / 4), to obtain 4.258 g of cholic acid active ester A, with a yield of 84.21%.

[0037] 2. Add 1563g (0.01mol) of glucosamine to a 100ml single-necked bottle, add 30ml of N,N-dimethylformamide / deionized water (2 / 1), then drop in 1.0119g (0.01mol) of triethyl Amine, stirred for 10 min, then added 5.057 g (0.01 mol) of ch...

Embodiment 2

[0043] Preparation of derivatives without polymerizable groups: cholic acid modified glucosamine derivatives, comprising the steps of:

[0044]Add 4.0858g (0.01mol) of cholic acid and 2.0269g (0.015mol) of 1-hydroxybenzotriazole into a 150ml three-necked flask, stir and dissolve in 30ml of tetrahydrofuran, and slowly add 3.8340g (0.02mol) of 10ml tetrahydrofuran solution of 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, keep warm for 2h, return to room temperature, continue to react for 24h, then stop the reaction, take the filtrate by suction filtration, remove by rotary evaporation solvent. Purify by silica gel column chromatography, the eluent is petroleum ether / ethyl acetate (1 / 4), to obtain 3.833 g of cholic acid active ester B with a yield of 75.79%.

[0045] 3. Add 23445g (0.015mol) of glucosamine into a 100ml single-necked bottle, add 30ml of N,N-dimethylformamide / deionized water (2 / 1), then drop in 1.9386g (0.015mol) of N, N-diisopropylethylamine, stirr...

Embodiment 3

[0048] Preparation of derivatives with polymerizable groups: acryloylcholic acid modified glucosamine derivatives, comprising the following steps:

[0049] Add 4.0858g (0.01mol) of cholic acid and 1.1509g (0.01mol) of N-hydroxysuccinimide into a 150ml three-necked flask, stir and dissolve in 30ml of tetrahydrofuran, and slowly add 1.8915g (0.015mol) of N , N'-diisopropylcarbodiimide in 10ml tetrahydrofuran solution, keep warm for 2h, return to room temperature, continue to react for 18h, then stop the reaction, filter the filtrate, and remove the solvent by rotary evaporation. Purified by silica gel column chromatography, the eluent was petroleum ether / ethyl acetate (1 / 4), to obtain cholic acid active ester A, with a mass of 4.258 g and a yield of 84.21%.

[0050] Add 2.5283g (0.005mol) of bile acid active ester A, 1.012g (0.01mol) of triethylamine (without water) into a 100ml single-necked bottle, add 30ml of tetrahydrofuran (without water) at 0°C, and cool with dry ice To -...

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Abstract

The present invention relates to a cholic acid-modified glucosamine derivative and a preparation method and application thereof, the derivative is shown as the formula (I), wherein R1 is H or OH, R2 is H or OH, and R3 is H, CH2 = CHCO-or CH2 = C (CH3) CO-. In the presence of a carbodiimide condensing agent, cholic acid is reacted with an excess amount of N-hydroxysuccinimide or 1-hydroxybenzotriazole to produce cholic acid active ester, the cholic acid active ester is then reacted with D-glucosamine to produce a derivative with no polymeric group; or the cholic acid active ester is first reacted with vinyl-containing acyl chloride, and then reacted with D-glucosamine to produce a derivative with a polymeric group; the derivative has good biocompatibility, the derivative with no polymeric group can be used as a drug for treatment of osteoarthritis, the derivative with the polymeric group can be used as a cartilage repair material organic matrix, or used for building in-situ formed glucosamine function hydrogel.

Description

technical field [0001] The invention relates to bile acid modified glucosamine derivatives and a preparation method thereof. The cholic acid-modified glucosamine derivatives of the invention can be used as medicine for treating osteoarthritis, organic matrix of cartilage repair materials, and can be used to construct in-situ shaped modified glucosamine functionalized hydrogel cartilage repair materials. Background technique [0002] As the final degradation product of chitin, D-glucosamine has the functions of treating arthritis, anti-inflammation, stimulating the synthesis of proteoglycans, immunoregulation, and participating in the construction of human tissues and cell membranes. It is an intermediate substance in the synthesis of proteoglycan macromolecules. Due to the physiological activity of these compounds, they are widely used in the fields of medicine and biology, and more and more attention has been paid to the research in related fields. Cholic acid is derived f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00A61K31/7008A61P19/02A61P29/00A61L27/20A61L27/52
CPCA61P19/02A61P29/00C07J41/0061
Inventor 任力侯思润刘卅姚航薛婧晨王迎军王琳
Owner SOUTH CHINA UNIV OF TECH
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