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Chitin sulfuric-ester hydroxy-benzene disulfonic acid derivative and production thereof

A technology of hydroxybenzene disulfonamide and chitosan sulfate, applied in the field of marine chemical engineering, can solve problems such as no relevant reports, and achieve the effects of expanding the application field, good water solubility, and enhancing biological activity

Inactive Publication Date: 2009-07-08
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, there is no relevant report on the research on the hydroxybenzenedisulfonamide derivatives of chitosan sulfate

Method used

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  • Chitin sulfuric-ester hydroxy-benzene disulfonic acid derivative and production thereof
  • Chitin sulfuric-ester hydroxy-benzene disulfonic acid derivative and production thereof
  • Chitin sulfuric-ester hydroxy-benzene disulfonic acid derivative and production thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 1g of chitosan C-6 sulfate with a molecular weight of 160,000 is dissolved in 50mL of 2% HAc, wherein the chitosan C-6 sulfate is referred to Concepts for improved regioselective placement of O-suifo, N-sulfo, N-acetyl , and N-carboxymethyl groups inchitosan derivatives; Hanno Baumann, Volker Faust; CarbohydrateResearch, 2001, 331, 43-57. The known method is prepared; under stirring, add 1.8g2-hydroxyl-5-chloro-1,3-benzenedi Sulfonyl chloride, react at 65°C for 5 hours. After cooling to room temperature, pour the reaction mixture into 300mL of acetone to make it completely precipitated. To obtain the precipitate, do not use too much acetone. After the precipitate is filtered, it is washed with acetone and dried at 50°C to obtain a brown powder. Use cyclohexane as the solvent After Soxhlet extraction for 8 hours, the hydroxybenzenedisulfonamide derivative of chitosan was obtained by vacuum drying. The structural formula is shown in formula 1, wherein n=496.

[0031] Inf...

Embodiment 2

[0033] The difference from Example 1 is:

[0034] 2g of chitosan C-6 sulfuric acid ester with a molecular weight of 04,000 was dissolved in 50mL of 1% HAc, and 3.45g of 2-hydroxy-5-chloro-1,3-benzenedisulfonyl chloride was added under stirring, and reacted at 75°C for 4 hours. After cooling, pour the reaction mixture into 400 mL of absolute ethanol to obtain a precipitate, filter the precipitate, wash with absolute ethanol, dry at 55°C to obtain a brown powder, use cyclohexane as a solvent for Soxhlet extraction for 8 hours, and then vacuum-dry to obtain the shell Hydroxybenzenedisulfonamide derivatives of polysaccharide sulfate esters, see formula 1 for the structural formula, wherein n=12.

[0035] Infrared spectroscopy analysis shows that the hydroxybenzenedisulfonamide derivatives of chitosan sulfate (see image 3 ) and chitosan sulfate (see figure 1), two new absorption peaks appear at 1530.48 and 1391.15, which are the characteristic absorption peaks of the hydroxybenz...

Embodiment 3

[0037] The difference from Example 1 is:

[0038] 2g of chitosan C-6 sulfate ester with a molecular weight of 50,000 was dissolved in 60mL of 1% HAc, and 2.25g of 2-hydroxy-5-chloro-1,3-benzenedisulfonyl chloride was added under stirring, and reacted at 65°C for 5 hours. After cooling, pour the reaction mixture into 300 mL of absolute ethanol to obtain a precipitate, filter the precipitate, wash with absolute ethanol, dry at 60°C to obtain a brown powder, use cyclohexane as a solvent for Soxhlet extraction for 8 hours, and then vacuum-dry to obtain the shell Hydroxybenzenedisulfonamide derivatives of polysaccharide sulfate esters, see formula 1 for the structural formula, wherein n=155.

[0039] Infrared spectroscopy analysis shows that the hydroxybenzenedisulfonamide derivatives of chitosan sulfate (see Figure 4 ) and chitosan sulfate (see figure 1 ) compared to 1398.06cm -1 The new absorption peak, which is the characteristic absorption peak of the hydroxybenzenedisulfon...

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Abstract

The invention relates to the technical field of marine chemical engineering, in particular to a hydroxybenzenedisulfonamide derivative of chitosan sulfate and a preparation method thereof. Specific derivatives are formula (1) or formula (2), wherein n=12-621. The preparation method comprises the following steps: reacting chitosan sulfate esters with different molecular weights with hydroxybenzenedisulfonyl chloride to prepare hydroxybenzenedisulfonamide derivatives of chitosan sulfate esters with different molecular weights. The hydroxybenzenedisulfonamide derivatives of chitosan sulfate were successfully synthesized by the preparation method of the present invention. The degree of substitution of these derivatives reaches 36.5-61.2%, and they have good water solubility. The effective combination of sulfonamide groups and chitosan sulfate molecules can produce synergistic effects and significantly enhance the unique properties of chitosan itself. Antibacterial, antiviral and other biological activities 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 hydroxybenzenedisulfonamide derivative of chitosan C-6 sulfuric acid ester and a preparation method thereof. Background technique [0002] The research and development of new veterinary drugs is a systematic project with high cost, long period, high technical requirements and high risk. It takes 10-15 years for a new drug to come out in foreign developed countries, costing hundreds of millions of dollars. Looking forward to the research and development trend of new veterinary drugs in the 21st century, with the development of pollution-free food, people pay more and more attention to the safety of livestock and poultry products. Animal toxicity is small, and requires less residue in animals. In order to meet this requirement, the production of veterinary drugs is basically becoming greener. In-depth research on the chemical and physiological activities of ...

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汲霞郭占勇王琳
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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