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A kind of cationic linear chloramine antibacterial agent and its synthetic method
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A cationic, synthetic method of technology, applied in the direction of fungicides, chemical instruments and methods, botany equipment and methods, etc., can solve environmental hazards and other problems, achieve the effect of improving antibacterial activity, improving antibacterial activity, and improving water solubility
Active Publication Date: 2021-06-15
DALIAN UNIV OF TECH
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However, the synthesis of hydantoin compounds requires highly toxic potassiumcyanide, which is extremely harmful to the environment
Method used
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Embodiment 1
[0025] Refer to the method in the literature (Cryst. Growth Des. 2008, 8, 2364-2376.): add 10 mL of dichloromethane to a constant pressure funnel and add chlorobutyryl chloride (5.04 g, 4.00 mL, 35.7 mmol) and mix well. Add 25mL dichloromethane in 100mL one-necked flask, then add tert-butylamine (2.62g, 3.79mL, 35.7mmol) and triethylamine (4.03g, 5.52mL, 39.9mmol), stir under ice-water bath condition until the temperature drops to 0 After ℃, slowly add the chlorobutyryl chloride solution dropwise into the flask, and control the dropping time over 30 minutes; remove the ice-water bath after the dropwise addition and stir at room temperature for 6 hours. After the reaction was completed, the inorganic salts were removed by filtration, concentrated in vacuo to remove the solvent, and purified by column chromatography, using ethyl acetate / petroleumether (15:85, v / v) as the eluent to obtain compound 1 as a white flaky solid (4.45g , 70.1%).
[0026] 1 H NMR (500MHz, CDCl3) δ5.31...
Embodiment 2
[0028] Compound 1 (0.70g, 3.94mmol) was dissolved in 8mL of ethanol, and then 30% trimethylamineaqueous solution (2.33g, 3.11mL, 11.8mmol) was added; fully refluxed overnight under stirring conditions. After the solvent was removed under vacuum, column chromatography was used to obtain compound 2 as a white powdery solid (0.70 g, 75.3%) using methanol / dichloromethane (1 / 4, v / v) as the eluent.
[0029] 1 H NMR (500MHz,D 2 O) δ3.27-3.19(m, 2H), 3.06(s, 9H), 2.21(t, J=7.2Hz, 2H), 2.02-1.90(m, 2H), 1.24(s, 9H); 13 C NMR (126MHz, D 2 O) δ173.3, 65.5, 52.9, 51.2, 32.5, 27.7, 18.8; HRMS calcd.for C 11 h 25 N 2 O[M-Cl] + 201.1963,found: 201.1967.
Embodiment 3
[0031] Compound 2 (0.50g, 2.11mmol) was dissolved in a mixed solution of 3.60mL tert-butanol and 0.9mL deionized water, and after complete dissolution, tert-butyl hypochlorite (0.80g, 0.84mL, 7.39mmol) was added dropwise at room temperature Avoid light and stir for 24h. Compound 3 was obtained as a white solid after concentration under reduced pressure.
[0032] 1 H NMR (500MHz,D 2 O) δ3.31-3.22(m, 2H), 3.07(s, 9H), 2.68(t, J=6.9Hz, 2H), 2.02-1.91(m, 2H), 1.43(s, 9H); 13 C NMR (126MHz, D 2 O) δ176.2, 65.6, 65.5, 52.8, 32.8, 28.1, 18.3; HRMS calcd.for C 11 h 24 N 2 OCl[M-Cl] + 235.1577,found: 235.1817.
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Abstract
The invention belongs to the technical field of synthesis and application of chloramine antibacterial agents, and provides a method for synthesizing cationic linear chloramine antibacterial agents, using N-tert-butyl-chloroalkylamide II and compound IV as raw materials to prepare chlorine Amine precursor compound III, and then react with tert-butyl hypochlorite at room temperature to obtain chloramine compound I; wherein compound IV is a tertiary amine compound IV with different alkyl chains 1 , Pyridine compounds with different alkyl chains Ⅳ 2 And one of tributylphosphine. In the preparation method of the present invention, while avoiding the use of potassiumcyanide, different cationic structures are introduced into linear chloramine molecules to improve water solubility and antibacterial activity; It can produce a strong synergistic antibacterial effect, and its antibacterial activity is significantly improved compared with hydantoin-like chloramines; it is expected to provide a theoretical basis for the preparation of efficient cationic chloramine antibacterial materials.
Description
technical field [0001] The invention belongs to the technical field of synthesis and application of chloramine antibacterial agents, and in particular relates to the synthesis of a class of cationic linear chloramine antibacterial agents. Background technique [0002] With the development of society and the improvement of people's living standards, infectious diseases caused by pathogens have increasingly become a major threat to human health and social well-being. Many pathogenic microorganisms have shown strong resistance to modern antibiotics, such as methicillin-resistant Staphylococcus aureus and Escherichia coli, so the development and use of high-efficiency broad-spectrum antibacterial agents is imminent. Antibacterial agents can inhibit the reproduction of bacteria, fungi and other microorganisms or kill microorganisms within a certain period of time, and can be mainly divided into inorganic antibacterial agents, organic antibacterial agents and natural antibacterial...
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