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Tri-cation quaternary ammonium salt antibacterial peptide simulant with antibacterial activity and preparation method thereof

A technology of triple cations and quaternary ammonium salts, which is applied in the preparation of organic compounds, aminohydroxy compounds, antibacterial drugs, etc., and can solve the problems of high cytotoxicity of host cells, high production costs, and large molecular weight

Active Publication Date: 2022-08-02
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as antimicrobial peptides are widely studied as a new type of antibacterial drug, more and more problems are exposed to researchers, especially in the development of drugs, which are limited by their own inherent shortcomings, such as large molecular weight, High production cost, easy to be degraded by protein enzymes, poor activity in the presence of salt substances, high cytotoxicity to host cells and poor pharmacokinetics, etc.

Method used

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  • Tri-cation quaternary ammonium salt antibacterial peptide simulant with antibacterial activity and preparation method thereof
  • Tri-cation quaternary ammonium salt antibacterial peptide simulant with antibacterial activity and preparation method thereof
  • Tri-cation quaternary ammonium salt antibacterial peptide simulant with antibacterial activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Preparation of Example 1 Compound 1a:

[0072] In a round-bottom flask (100 mL), phloroglucinol (7.93 mmol, 1 eq.) was dissolved in acetone (20 mL), then solid potassium carbonate (35.68 mmol, 4.5 eq.) was added, and 3-bromo was added after stirring evenly. -1-Propanol (35.68mmol, 4.5eq.), heated to reflux at 65°C, and reacted for 24h. After the reaction, the solvent was concentrated and removed, ethyl acetate (100 mL) and water (100 mL) were added to dissolve and dilute the solid, the organic phase was washed three times with water (100 mL), the organic phase was retained and washed with saturated sodium chloride solution (10 mL, 1- 3 times) and dried over anhydrous sodium sulfate, filtered after drying, and the organic phase was concentrated. Weigh the concentrated product (3 g, 1 eq.), transfer it to a clean reactor, add dichloromethane (50 mL) to dissolve, and add phosphine tribromide (19.98 mmol, 2 eq.) dropwise to the system under an ice-water bath. , after the ...

Embodiment 2

[0074] Preparation of Example 2 Compound 1b:

[0075] In a round bottom flask (100 mL), dissolve phloroglucinol (7.93 mmol, 1 eq.) in N,N-dimethylformamide (20 mL), then add potassium carbonate solid (35.68 mmol, 4.5 eq.) , After stirring evenly, dibromobutane (35.68mmol, 4.5eq.) was added, and the reaction was carried out at room temperature for 24h. After the reaction, ethyl acetate (100 mL) and water (100 mL) were added to dilute the system, extracted, and the organic phase was retained. The organic phase was washed 3-5 times with water (100 mL), and washed with saturated sodium chloride solution (10 3 times) and anhydrous sodium sulfate to dry the organic phase, filter and concentrate the organic phase, and use column separation to purify the product (petroleum ether:ethyl acetate=20:1, V:V).

[0076] 1b: Yield 49%. 1 H NMR (400MHz, Chloroform-d) δ6.05(s, 3H), 3.95(t, J=6.0Hz, 6H), 3.48(t, J=6.6Hz, 6H), 2.10–2.01(m, 6H) ,1.93(m,6H). 13 C NMR (101MHz, Chloroform-d) δ160...

Embodiment 3

[0077] Example 3 Preparation of compound 1c: The preparation method was the same as that of Example 2, and the dibromoalkane used was dibromopentane.

[0078] 1c: Yield 47%. 1 H NMR (400MHz, Chloroform-d) δ6.05(s, 3H), 3.92(t, J=6.3Hz, 6H), 3.43(t, J=6.8Hz, 6H), 1.98–1.88(m, 6H) ,1.84–1.74(m,6H),1.66–1.57(m,6H). 13 CNMR (101MHz, Chloroform-d) δ160.81, 93.88, 67.59, 33.61, 32.47, 28.39, 24.86.

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Abstract

The invention belongs to the technical field of medicinal chemistry, and discloses a tri-cationic quaternary ammonium salt antibacterial peptide simulant with antibacterial activity and a preparation method thereof. The compounds have the following structural general formulas I-III. In-vitro antibacterial activity experiments prove that a part of the series of compounds show good activity on gram-positive bacteria staphylococcus aureus and enterococcus faecalis and gram-negative bacteria escherichia coli and stenotrophomonas maltophilia, and the compounds have excellent broad-spectrum antibacterial activity; meanwhile, in-vitro red blood cell hemolytic data show that the compound is relatively low in hemolytic toxicity and relatively good in selectivity.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and discloses a tricationic quaternary ammonium salt antibacterial peptide mimetic with antibacterial activity and a preparation method thereof. Background technique [0002] The discovery and widespread use of antibiotics are of indelible significance in the development of human civilization. According to different mechanisms, they are divided into aminoglycosides, tetracyclines, chloramphenicol, macrolides, and lincomycin that affect bacterial protein synthesis. β-lactams that interfere with bacterial cell wall synthesis; polymyxins that damage bacterial cell membranes, sulfonamides and trimethoprim that interfere with folic acid metabolism; quinolones that affect nucleic acid metabolism, etc. However, with the rapid development of society and economy, antibiotic resistance (AMR) has become the main threat to public health from bacteria since the era of antibiotics. Bacterial drug ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/18C07C213/08A61P31/04
CPCC07C217/18A61P31/04Y02A50/30
Inventor 张恩李雯闫大钞秦上尚沈渤渊李森王梦陈胜聪高辰麦斯威尔
Owner ZHENGZHOU UNIV
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