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Quaternary phosphonium salt type N-halamine antibacterial agent and preparation method thereof

A technology of quaternary phosphonium salt and antibacterial agent, which is applied in the field of quaternary phosphonium salt type haloamine antibacterial agent molecule and its preparation, and can solve the problems of poor water solubility of haloamine antibacterial agent

Inactive Publication Date: 2015-09-16
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to prepare a novel antibacterial agent: a chemical synthesis strategy is adopted to integrate the halamine group and the quaternary phosphonium salt group into the same small molecule, which solves the problem of poor water solubility of the halamine antibacterial agent on the one hand, and on the other hand Obtain more active antibacterial molecules on the one hand; Another object of the present invention is to provide the preparation method of above-mentioned quaternary phosphonium salt type haloamine antibacterial agent

Method used

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  • Quaternary phosphonium salt type N-halamine antibacterial agent and preparation method thereof
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  • Quaternary phosphonium salt type N-halamine antibacterial agent and preparation method thereof

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Embodiment 1

[0030] First add 4 g (about 31.2 mmol) of 5,5-dimethylhydantoin into a 500 mL single-necked flask, then add 200 mL of acetone, and place the flask in an oil bath to preheat. After the solid dissolves, add about 17g K 2 CO 3 (about 123.2mmol), add 40-50mL of acetone, reflux for 0.5h, add 18.9g of 1,3-dibromopropane (about 9.6mL, 93.7mmol) into the reactor, and continue to heat and reflux overnight. Wash with 100mL of water for several times, remove the inorganic salt impurities from the reacted mixture, and remove the solvent under vacuum to obtain a crude product. Column chromatography can further improve its purity, and the yield is about 85%. The product structure is shown in the following formula :

[0031]

[0032] First 3.0g (about 12.1mmol) of compound 1 was dissolved in about 50mL of acetonitrile, and N was introduced into the reactor. 2 Exhaust the air, then inject 1.6g (about 2mL, 8.0mmol) of tributylphosphine into the reactor with a syringe, heat to reflux for ...

Embodiment 2

[0041] Dissolve 3.2 g (about 25.3 mmol) of 5,5-dimethylhydantoin in about 200 mL of acetone, and add K to the reactor after the dissolution is complete. 2 CO 313.8g (about 101.2mmol), heated to reflux for 0.5h, then added 24.9g (about 75.9mmol) of 1,12-dibromododecane into the reactor, continued to reflux for about 24h, then stopped the reaction. After removing the inorganic salt impurities, concentrate and remove the solvent under vacuum conditions, and then obtain compound 17 after purification by column chromatography, the yield is above 70%, and the structure is shown in the following formula:

[0042]

[0043] 2.5 g of compound 5 (about 6.7 mmol) was dissolved in 40 mL of acetonitrile. After the dissolution is complete, feed N into the reactor 2 Bleed out the air completely. Then inject 1.2 g of tributylphosphine (about 1.5 mL, 6.0 mmol) into the reactor, continue to heat and reflux for 48 h, and stop the reaction. The reaction solution was concentrated under vacuu...

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Abstract

The invention discloses a small molecule quaternary phosphonium salt type N-halamine antibacterial agent and a preparation method thereof. The antibacterial agent is prepared by integrating a quaternary phosphonium salt group and a N-halamine group into a single molecule by chemical covalent bond, solves the problem of poor hydrophily of N-halamine molecules, and retains the respective advantages of two antibacterial agents including N-halamine and quaternary phosphonium salt unit respectively, the antibacterial agent is good in sterilization effect, cost is low, technological process is simple, and the small molecule quaternary phosphonium salt type N-halamine antibacterial agent is suitable for medical treatment and public health, food safety, environmental protection, and many other fields.

Description

technical field [0001] The invention relates to antibacterial agents, in particular to a class of quaternary phosphonium salt-type haloamine antibacterial agent molecules and a preparation method thereof, belonging to the field of antibacterial technology. Background technique [0002] With the advancement of the times and technology, people have higher and higher requirements for the environment and health. As an effective means against pathogenic bacteria and viruses, antibacterial agents have been widely used in many aspects such as medical and health care, food processing, clothing processing, and environmental governance. [0003] Antibacterial agents refer to a class of chemical substances that can kill microorganisms or inhibit the growth and reproduction of microorganisms, and have certain inactivation or growth inhibition effects on bacteria, fungi, and spores. Its functions are divided into two types: antibacterial and bactericidal. Antibacterial is to delay and h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6506A01N57/24A01P1/00
Inventor 李令东闫超陈洪媛
Owner DALIAN UNIV OF TECH
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