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Betaine type chloramine antibacterial agent and synthetic method thereof

A synthesis method and technology of betaine, which are applied in botany equipment and methods, biocides, disinfectants, etc., can solve problems such as poor dispersion, poor hydrophilicity of chloramine antibacterial agents, unfavorable sterilization process and sterilization effect, etc. To achieve the effect of improving water solubility

Active Publication Date: 2018-08-10
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the hydrophilicity of chloramine antibacterial agents is often not good, and the dispersion in the aqueous system is poor, which is very unfavorable for its sterilization process and bactericidal effect

Method used

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  • Betaine type chloramine antibacterial agent and synthetic method thereof
  • Betaine type chloramine antibacterial agent and synthetic method thereof
  • Betaine type chloramine antibacterial agent and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Compound 1 (0.82g, 3.86mmol) was dissolved in 2mL of acetonitrile, then 1,2-dibromoethane (7.29g, 38.6mmol) was added, and heated to reflux for 24h. Concentrated under reduced pressure to remove the solvent, followed by column chromatography separation and purification, using methanol and dichloromethane (1 / 19, v / v) as eluents, collecting the organic phase containing the product to obtain compound 2 as a fluffy light yellow solid (1.06 g, 68.2%).

[0026] 1 H NMR (500HMz,D 2 O)δ3.76-3.73(m,2H),3.71-3.68(m,2H),3.52(t,J=6.8Hz,2H),3.37-3.34(m,2H),3.08(s,6H), 2.10-2.04(m,2H),1.35(s,6H); 13 CNMR (126MHz,D 2 O) δ180.6, 157.1, 63.9, 62.0, 59.2, 50.9, 35.3, 23.4, 21.3, 20.6. HRMS calcd.for C 12 h 23 N 3 o 2 Br[M-Br] + 320.0974,found: 320.0986.

Embodiment 2

[0028] Compound 2 (0.87g, 2.16mmol) was dissolved in 5mL of water, then sodium sulfite (0.43g, 3.40mmol) was added, and reacted at 90°C for 24h. After the reaction stopped, remove the water, add 12mL of methanol under heating conditions to dissolve, filter to remove insoluble salts, concentrate the filtrate under reduced pressure, carry out column separation and purification, and elute with methanol and dichloromethane (1 / 1, v / v) The organic phase containing the product was collected to give a fluffy solid (0.50 g, 72.6%). The solid was recrystallized, dissolved in about 10mL of methanol under heating, and about 70mL of acetone was added under stirring, a white floc was formed, and after standing, it was filtered to obtain compound 5 as a white solid (0.43g, 86%)

[0029] 1 H NMR (500HMz,D 2 O)δ3.64-3.60(m,2H),3.51(t,J=6.8Hz,2H),3.34-3.31(m,4H),3.07(s,6H),2.09-2.03(m,2H), 1.34(s,6H); 13 C NMR (126MHz,D 2 O) δ180.5, 157.0, 61.8, 59.3, 59.1, 50.9, 44.0, 35.2, 23.4, 21.3. HR...

Embodiment 3

[0031] Compound 5 (0.50g, 1.57mmol) was dissolved in a mixed solution of 4mL tert-butanol and 1mL deionized water, and after complete dissolution, tert-butyl hypochlorite (0.51g, 4.70mmol) was added dropwise, and stirred at room temperature for 36h in the dark . Compound 8 was obtained as a white solid (0.53 g, 95.5%) after concentration under reduced pressure.

[0032] 1 H NMR (500HMz,D 2 O) δ3.64-3.58(m,4H),3.37-3.31(m,4H),3.07(s,6H),2.12-2.06(m,2H),1.41(s,6H); 13 C NMR (126MHz, D 2 O) δ176.7, 155.4, 66.3, 61.7, 59.3, 50.9, 44.0, 36.4, 21.2, 20.9. HRMS calcd.for C 12 h 22 N 3 o 5 SCl[M+Na] + 378.0866,found: 378.0864.

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Abstract

The invention provides a betaine type chloramine antibacterial agent and a synthetic method thereof and belongs to the technical field of chemical synthesis and application of chloramine antibacterialagents. The antibacterial agent takes bromoalkyl 5,5-dimethylhydantoin II and dimethylamine hydrochloride as raw materials, and a chloramine precursor compound IV1 / IV2 is prepared through different chemical synthesis routes and then reacts with excessive tertiary butyl hypochlorite under normal temperature conditions to prepare an antibacterial agent compound I1 / I2. The antibacterial agent provided by the invention integrates a chloramine group with a salt group in betaine in a molecule, so that while the hydrophilicity of the chloramine compound is improved, a synergistic bactericidal effectof betaine structure units with different structures and the chloramine group is realized. Escherichia coli and staphylococcus aureus are taken as model strains; antibacterial test results show thatthe bactericidal activity of the carboxylic acid inner salt type chloramine antibacterial agent is significantly better than that of a previously-reported quaternary ammonium salt type chloramine antibacterial agent, and the antibacterial activity is slightly inferior to that of a quaternary ammonium chloride antibacterial agent.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis and application of chloramine antibacterial agents, and in particular relates to the synthesis of sulfonate betaine type chloramine antibacterial agents and carboxybetaine type chloramine antibacterial agents. Background technique [0002] In recent years, the spread of infectious diseases caused by pathogenic microorganisms has occurred frequently, seriously threatening people's health and quality of life. In order to effectively inhibit the spread and spread of bacteria, the development of new antibacterial agents has become a very urgent research task today. Antibacterial agents are a class of chemical substances that can effectively inhibit the reproduction of bacteria, fungi and other microorganisms or kill microorganisms within a certain period of time. Among them, chloramine antibacterial agents have attracted much attention due to their advantages of rapid sterilization, long-te...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/50A01P1/00C07D233/82C07D233/74
CPCA01N43/50C07D233/74C07D233/82
Inventor 李令东靳亚楠王翰德王鹏飞
Owner DALIAN UNIV OF TECH
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