Antibacterially active linezolid alkali cation amphiphilic compounds and synthesis method thereof

A technology for linezolid base cationic amphiphilic compounds, which is applied in the field of linezolid base cationic amphiphilic compounds and their preparation, can solve the problem that the antibacterial activity of the compound has not been significantly improved, and achieve broad-spectrum antibacterial activity, good Bacteriostatic effect, selective effect

Active Publication Date: 2017-11-24
ZHENGZHOU UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

At present, a lot of research work has been devoted to the synthesis of oxazolidinone analogs (Antimicrobial agents and chemotherapy, 2001.45 (4): p.1151-1161), and the modification of other groups by retaining the active group morpholine and amide (Biomacromolecules

Method used

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  • Antibacterially active linezolid alkali cation amphiphilic compounds and synthesis method thereof
  • Antibacterially active linezolid alkali cation amphiphilic compounds and synthesis method thereof
  • Antibacterially active linezolid alkali cation amphiphilic compounds and synthesis method thereof

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Embodiment 1

[0029] Example 1 Preparation of Compounds 2a~2f, 6a~6j

[0030] (1) Synthesis of compound (1a):

[0031] Synthesis of compound (1a): Add solvent acetone (25mL) to a flask containing a mixture of linezolid base (1g, 3.39mmol) and anhydrous potassium carbonate (562mg, 4.06mmol), then cover with a rubber stopper, and then use a syringe Chloroacetyl chloride (306 μL) was added, and the reaction was stirred at room temperature. After 0.5-1 h of reaction, the reaction was quenched with ice water, and a precipitate was precipitated, filtered with suction, washed with ice water, and the filter cake was dried in a vacuum oven to obtain the target product.

[0032] (2) Synthesis of compound (2a-2f):

[0033] Synthesis of compounds (2a-2f): Add solvent acetonitrile to the hydrothermal synthesis reactor containing compound 1a, and then add N,N-dimethyl n-alkylamine (1a: N,N-dimethyl n-alkyl Amine=1:3, molar ratio), and then stirred and reacted in an oil bath at 85°C. After reacting for...

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Abstract

The invention belongs to the field of medicinal chemistry, and discloses antibacterially active linezolid alkali cation amphiphilic compounds and a synthesis method thereof. Three target products are obtained simply and quickly through a two-step or three-step reaction. The main structure is as follows: in-vitro antibacterial activity experiments show that the series of compounds show good antibacterial effects on sensitive strains such as staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Salmonella enteric, and some of the compounds show excellent antibacterial effects on super bacteria including methicillin-resistant staphylococcus aureus (MRSA), vancomycin-resistant enterococci (VRE) and carbapenemases-producing Enterobacteriaceae (CRE). In-vitro erythrocytotoxicity experiments show that the series of compounds have less erythrocytotoxicity, and the series of compounds are expected to be used as new antibacterial drug candidates.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and discloses a linezolid base cationic amphiphilic compound with antibacterial activity and a preparation method thereof. Background technique [0002] Since its launch in 2000, linezolid has been used in the United States to treat Gram-positive cocci (AntimicrobAgents Chemother, 2010, 54, 742), including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci ( VRE). However, it has been reported that drug-resistant bacteria such as VRE and MRSA are resistant to linezolid (The Lancet, 2001, 358, 207), and MRSA is the most common drug-resistant bacteria in the world (The Lancet, 2006, 368, 874). [0003] Therefore, designing and synthesizing new antibacterial drugs is one of the main goals of drug researchers in the future. At present, a lot of research work has been devoted to the synthesis of oxazolidinone analogs (Antimicrobial agents and chemother...

Claims

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Application Information

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IPC IPC(8): C07D263/20A61P31/04
CPCC07D263/20Y02A50/30Y02P20/55
Inventor 张恩秦上尚白鹏燕楚文超崔得运化永刚殷海洋张勇杰陈雅欣王子扬王亚娜刘宏民
Owner ZHENGZHOU UNIV
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