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Chitin sulfanilamide derivative and its production

A technology of chitosan and derivatives, applied in the field of chitosan and its C-6 sulfuric acid ester sulfonamide derivatives and its preparation, can solve the problems of poor effect, achieve good water solubility and enhance antibacterial Active, wide-ranging effects

Inactive Publication Date: 2009-09-23
INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, it has been reported that chitosan is used as an additive in veterinary medicine, which can enhance the immune function of the body and improve the disease resistance of farmed animals, but the effect is not good.

Method used

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  • Chitin sulfanilamide derivative and its production
  • Chitin sulfanilamide derivative and its production
  • Chitin sulfanilamide derivative and its production

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Take 2g with HAc-H 2 o 2 The chitosan with a degraded molecular weight of 4,000 has a deacetylation degree of 80%. Dissolve in 100 mL of dimethyl sulfoxide, add 5.78 g of p-acetamidobenzenesulfonyl chloride dissolved in 20 mL of dimethyl sulfoxide under stirring, and react at 65°C for 3 hours. After cooling, pour the reaction mixture into 300mL acetone to obtain a precipitate, filter and wash the precipitate with acetone, add 100mL distilled water to dissolve, put it into a dialysis bag with a molecular weight of 3600, dialyze with distilled water for 2-3 days, and concentrate to about 30mL by rotary evaporation. Chitosan sulfonamide derivatives (as shown in Formula 1, wherein n=25) were obtained after freeze-drying, wherein the degree of substitution of sulfonamide groups was 40.2%.

[0029]

[0030] Infrared spectroscopy analysis showed that (see image 3 ), chitosan sulfonamide derivatives and chitosan (see figure 1 ) compared with 1358.32, 1163.02 and 824.67 ...

Embodiment 2

[0032]2g chitosan, its molecular weight is about 200,000, the degree of deacetylation is 96%, dissolve in 80mL formamide, add 2.89g p-acetamidobenzenesulfonyl chloride dissolved in 20mL formamide under stirring, and react at 75°C for 3 hours . After cooling, pour the reaction mixture into 200 mL of absolute ethanol to obtain a precipitate, filter and wash the precipitate with acetone, add 100 mL of distilled water to dissolve, put it into a dialysis bag with a molecular weight of 3600, dialyze with distilled water for 2-3 days, and concentrate to 30 mL by rotary evaporation Left and right, chitosan sulfonamide derivatives are obtained after freeze-drying, the structure is shown in formula 1, wherein n=1242.

[0033] Infrared spectroscopy analysis showed that (see Figure 4 ), chitosan sulfonamide derivatives and chitosan (see figure 1 ) compared with 1376.69, 1166.54 and 836.15 three new absorption peaks, which are the characteristic absorption peaks of the sulfonamide group...

Embodiment 3

[0035] Chitosan sulfate used as raw material is prepared from chitosan by known methods, such as using chitosan and sulfonating reagent DMF-SO 3 The reaction gives chitosan sulfate. (Preparation of high-molecular weight and high-sulfate content chitosans and their potential antioxidant activity in vitro, Ronge Xing; Song Liu; HuahuaYu; Zhanyong Guo; Zhien Li; Pengcheng Li, Carbohydrate Polymers, 2005, 61(2), 148-154. ) Get 2g of chitosan sulfate, its molecular weight is 09,000, and the S content is 10.55%. Dissolve in 50 mL of dimethyl sulfoxide, add 2.91 g of p-acetamidobenzenesulfonyl chloride dissolved in 20 mL of dimethyl sulfoxide under stirring, and react at 65°C for 4 hours. After cooling, pour the reaction mixture into 300mL acetone to obtain a precipitate, wash the precipitate with acetone after filtration, add 50mL distilled water to dissolve, put it into a dialysis bag with a molecular weight of 3600, dialyze with distilled water for 2-3 days, and concentrate to ab...

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Abstract

The invention relates to the technical field of marine chemical engineering, in particular to a sulfonamide derivative of chitosan and its C-6 sulfate ester and a preparation method thereof. The chemical formula of the specific derivative is: see the right formula, wherein R is SO3- or see the right formula, n=18-1243. The preparation method comprises: reacting chitosan or chitosan C-6 sulfate ester with different molecular weights with p-acetamidobenzenesulfonyl chloride to prepare chitosan or chitosan sulfate sulfonamide derivatives with different molecular weights. The preparation method of the present invention synthesizes the sulfonamide derivatives of chitosan and its sulfuric acid esters, the degree of substitution of which derivatives reaches 35.6-59.8%, and has good water solubility, and the sulfonamide group and chitosan and its sulfuric acid The effective combination of esters can produce a synergistic effect, significantly enhance the unique biological activity of chitosan itself, and can be used in medicine, cosmetics, agriculture and other fields.

Description

technical field [0001] The invention relates to the technical field of marine chemical engineering, in particular to a sulfonamide derivative of chitosan and its C-6 sulfate ester and a preparation method thereof. Background technique [0002] The veterinary drug industry is a high-tech industry. The development of new veterinary drugs is expensive, risky, and takes a long time. Sometimes tens of thousands of derivatives must be screened to obtain a marketed product. According to statistics from the Pharmaceutical Manufacturers of America (PMA), it takes an average of 12 years for each drug to go from preclinical testing to FDA approval. The time taken to develop a new chemical entity (NCE) has increased from 7.7 years in the early 1970s to 12.8 years in the early 1990s; in terms of cost, it only cost tens of millions of dollars to develop a new drug in the past, while Current research and development costs generally range from $250 million to $350 million. [0003] In-dep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08A61K31/722
Inventor 李鹏程钟志梅邢荣娥刘松郭占勇汲霞
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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