Quatemary ammonium chalcone derivatives resistant to drug-resistance bacteria activities, preparation method and application of quatemary ammonium chalcone derivatives

A technology of chalcone derivatives and drug-resistant bacteria, which is applied in the preparation of organic compounds, antibacterial drugs, and carboxylic acid amides, and can solve problems such as weak selectivity, difficult mass production, and high toxicity of antibacterial peptides

Active Publication Date: 2017-10-10
ZHENGZHOU UNIV
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Problems solved by technology

Due to its positive charge, it can combine with the anions on the surface of the bacterial membrane to enhance the binding ability with the bacterial membrane. However, due to the high production cost of natural antimicrobial peptides, it is not easy to mass-produce, and it is easy to be degraded in the body. Some antimicrobial peptides are highly toxic and have weak selectivity.

Method used

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  • Quatemary ammonium chalcone derivatives resistant to drug-resistance bacteria activities, preparation method and application of quatemary ammonium chalcone derivatives
  • Quatemary ammonium chalcone derivatives resistant to drug-resistance bacteria activities, preparation method and application of quatemary ammonium chalcone derivatives
  • Quatemary ammonium chalcone derivatives resistant to drug-resistance bacteria activities, preparation method and application of quatemary ammonium chalcone derivatives

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Embodiment 1

[0024] The preparation of embodiment 1 compound f1-f28

[0025] (1) Preparation of compound c1-c22

[0026] Take sodium hydroxide (110.97mg, 2.77mmol) in a single-necked round bottom flask (200mL), add water (25mL) and dissolve under magnetic stirring at room temperature; then compound a p-aminoacetophenone (300.00mg, 2.22mmol) and compound Add b1-b22 (2.26mmol) into the Erlenmeyer flask (100mL), add absolute ethanol (25mL) and sonicate until the system is clear, then add the clear solution dropwise (1 drop / second) to the above-mentioned stirred hydrogen In the single-necked bottle of sodium oxide solution, after the dropwise addition, the reaction was continued at room temperature, and the system was brownish yellow and clear. After about 6 hours, TLC (PE:EA=1:1) detection showed that the reaction was complete. The reaction was stopped, and the reaction system was poured into ice water (50 mL), and a large amount of yellow solid was precipitated immediately, filtered with s...

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Abstract

The invention belongs to the technical field of medicinal chemistry, and discloses quatemary ammonium chalcone derivatives resistant to drug-resistance bacteria activities, a preparation method and application of the quatemary ammonium chalcone derivatives. A structural formula is as shown in the description. Proved by invitro antibacterial activity experiments and erythrocyte hemolytic experiments, a large part of compounds in the series of the derivatives have great antibacterial effects and selections on staphylococcus aureus and colonic enterococcus faecalis of gram-positive bacteria, escherichia coli and pseudomonas aeruginosa of gram-negative bacteria. The selected part of compounds show great antimicrobial activities on a plurality of 'superbacteria' including methicillin-resistant staphylococcus aureus (MRSA), vancomycin resistant enterococcus (VRE), carbapenem-resistant enterobacteriaceae (CRE) and new delhi metallo (NDM) carrying NDM genes, and especially show excellent activities on the MRSA. Proved by invitro erythrocyte toxicity experiments, the series of compounds are low in erythrocyte toxicity and can be adopted as new anti-microbial drug candidates.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and discloses quaternary ammonium chalcone derivatives with anti-drug-resistant bacteria activity, their preparation method and their application as a class of novel anti-drug-resistant bacteria drugs. Background technique [0002] In the 1930s, the world's first antibiotic, penicillin, came out, bringing good news to countless patients and surgeons. With the development of science and technology, coupled with people's misunderstanding of antibiotics, the overuse of antibiotics has been accelerated, leading to the increasingly serious problem of bacterial acquired drug resistance, and the proportion of drug-resistant bacteria has increased year by year. According to the national bacterial drug resistance surveillance results of the Ministry of Health in the first half of 2016, bacterial drug resistance tests in 30 hospitals across the country showed that MRSA is resistant to 75% of co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/50C07D213/61C07D307/46C07D333/22C07C237/04C07C231/12A61P31/04
CPCC07C221/00C07C231/02C07C231/12C07C237/04C07D213/50C07D213/61C07D307/46C07D333/22C07C233/33C07C225/22Y02A50/30
Inventor 张恩秦上尚楚文超白鹏燕杨兆青崔得运化永刚王铭铭王亚娜刘宏民
Owner ZHENGZHOU UNIV
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