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Water-soluble beta-cyclodextrin amidate derivative and synthetic method and application in antioxidant and antibacterial fields

A cyclodextrin amide and derivative technology, which is used in water-soluble beta-cyclodextrin amidated derivatives, antibacterial applications, and anti-oxidation fields, can solve the problem of low solubility of cyclodextrin, obstacles and limitations in the recognition of drug guest molecules application and other issues, to achieve the effects of improving water solubility, good anti-oxidation, and simple operation

Active Publication Date: 2018-12-07
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The solubility of cyclodextrin in water is very small, and the recognition of drug guest molecules is hindered, which limits its application in the field of medicine. Therefore, the synthesis of β-cyclodextrin derivatives is more and more popular.

Method used

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  • Water-soluble beta-cyclodextrin amidate derivative and synthetic method and application in antioxidant and antibacterial fields
  • Water-soluble beta-cyclodextrin amidate derivative and synthetic method and application in antioxidant and antibacterial fields
  • Water-soluble beta-cyclodextrin amidate derivative and synthetic method and application in antioxidant and antibacterial fields

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of β-cyclodextrin amidated derivatives with the following structural formula

[0042]

[0043] 1. Synthesis of β-cyclodextrin sulfonylated derivatives

[0044] Dissolve 17.22g (0.015mol) of β-cyclodextrin in 200mL of 0.25mol / L sodium hydroxide aqueous solution, and add dropwise 16.5mL of acetonitrile solution in which 4.35g (0.023mol) of p-toluenesulfonyl chloride is dissolved in the solution. React at room temperature for 3 hours, filter with suction, adjust the pH of the filtrate to 2 with hydrochloric acid, and let it stand overnight at 4°C. A large amount of white solid precipitates, filter with suction, recrystallize with deionized water, and dry under vacuum at 40°C After 5 hours, the white powder product β-CD-6-OTs was obtained.

[0045] The structure of the obtained β-CD-6-OTs was characterized by mass spectrometer and nuclear magnetic resonance spectrometer, and the results are shown in figure 1 and figure 2 . The relative molecular weight of ...

Embodiment 2

[0053] Synthesis of β-cyclodextrin amidated derivatives with the following structural formula

[0054]

[0055] In this example, the ferulic acid in Example 1 was replaced with equimolar coumaric acid (p-CA), and the other steps were the same as in Example 1, and the obtained yellow solid β-cyclodextrin amidated derivative was denoted as β-CD-6-p-CA, its yield was 50.71%.

[0056] The obtained β-CD-6-p-CA was characterized by mass spectrometer and nuclear magnetic resonance spectrometer, the results are shown in Figure 7 and Figure 8 . The relative molecular weight of this compound is 1322.4720, by Figure 7 It can be seen that the molecular ion peak of its mass spectrum is 1323.4710, and the corresponding ion peak is M + ; Figure 8 In , each hydrogen in the compound can have a one-to-one correspondence with the chemical shift and integral on the hydrogen spectrum, and the specific data are: 1 H NMR(400MHz,DMSO):δ:2.09-2.01(m,1H,NH),2.32-2.34(m,2H,CH 2 ),2.43-2.45...

Embodiment 3

[0058] Synthesis of β-cyclodextrin amidated derivatives with the following structural formula

[0059]

[0060] In this example, equimolar caffeic acid (CA) was used to replace the ferulic acid in Example 1, and the other steps were the same as in Example 1, and the obtained yellow solid β-cyclodextrin amidated derivative was denoted as β-CD -6-CA, the yield of which was 60.12%.

[0061] The structure of the obtained β-CD-6-CA was characterized by mass spectrometer and nuclear magnetic resonance spectrometer, and the results are shown in Figure 9 and Figure 10 . The relative molecular weight of this compound is 1338.4669, by Figure 9 It can be seen that the molecular ion peak of its mass spectrum is 1339.4659, and the corresponding ion peak is M + ; Figure 10 In , each hydrogen in the compound can have a one-to-one correspondence with the chemical shift and integral on the hydrogen spectrum, and the specific data are: 1 H NMR(400MHz,DMSO):δ:2.09-2.01(m,1H,NH),2.32...

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Abstract

The invention discloses a water-soluble beta-cyclodextrin amidate derivative and a synthetic method and an application in antioxidant and antibacterial fields. The structural formula of the derivativeis as shown in a formula in the specification, in which R1, R2, R3, R4 and R5 independently represent any one of H, OH, C1-2 alkoxyl and C1-3 alkyl, and at least one of R1, R2, R3, R4 and R5 is OH. Aformula in the specification represents 6-site dehydroxyl beta-cyclodextrin. The derivative is prepared from raw materials of a cinnamic acid derivative, beta-cyclodextrin, paratoluensulfonyl chloride, ethidene diamine and the like through sulfonylation reaction, amination reaction and amidation. The synthetic method is cheap and easily available in raw material, simple to operate and mild in condition. The synthesized beta-cyclodextrin amidate derivative is relatively high in purity and good in water solubility. Moreover, the synthesized beta-cyclodextrin amidate derivative has excellent antioxidant and antibacterial performances without inclusion of functional guest molecules.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and fine chemical industry, and specifically relates to a water-soluble β-cyclodextrin amidated derivative, a synthesis method of the compound and applications in anti-oxidation and antibacterial aspects. Background technique [0002] Cyclodextrin (cyclodextrin, CD) mainly refers to the degradation product obtained by the action of cyclodextrin glycosyltransferase on starch. Cyclodextrin is a typical renewable, non-toxic and biodegradable resource, and has a special structure and properties of "hydrophobic in the inner cavity and hydrophilic in the outer wall", and has become an excellent structural unit for building various functional materials. Dextrin is cheap and easy to get, and it is the most widely used. [0003] The solubility of cyclodextrin in water is very small, and the recognition of drug guest molecules is hindered, which limits its application in the field of pharmacy. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16
CPCC08B37/0012
Inventor 陈亚芍张晶王长号张冬梅董梦瑾
Owner SHAANXI NORMAL UNIV
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