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Benzene ring substituted N-acyl homoserine lactone compounds as well as preparation method and application thereof

A technology for acyl homoserine and ester compounds, which is applied in the field of medicinal chemistry and achieves the effects of simple preparation method, mild conditions and high yield

Active Publication Date: 2017-05-31
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Modify the acyl side chain of homoserine lactone, synthesize derivatives containing benzene ring structure, study its quorum sensing inhibitory activity, and develop new antibacterial quorum sensing, antibacterial synergists, antibacterial or antitumor drugs Drugs with independent intellectual property rights are of great significance, and there are no relevant literature reports so far

Method used

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  • Benzene ring substituted N-acyl homoserine lactone compounds as well as preparation method and application thereof
  • Benzene ring substituted N-acyl homoserine lactone compounds as well as preparation method and application thereof
  • Benzene ring substituted N-acyl homoserine lactone compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: prepare derivative (3-a) shown in general formula 3

[0028] Compound (S)-2-chloro-N-(2-carbonyltetrahydrofuran-3-yl)propionamide (150mg, 0.79mmol), potassium carbonate (109mg, 0.79mmol) was dissolved in 10mL of acetonitrile, heated to 80°C , added p-chlorothiophenol (114mg, 0.79mmol), after constant temperature reaction for 4h, TLC tracked the completion of the reaction, suction filtered, removed potassium carbonate, evaporated the solvent under reduced pressure, and separated by silica gel column chromatography (eluent: ethyl acetate / Petroleum ether=1 / 1) to obtain 183 mg of off-white solid, namely compound (3-a), with a yield of 78%.

Embodiment 2

[0029] Embodiment 2: prepare derivative (3-b) shown in general formula 3

[0030] Compound (S)-2-chloro-N-(2-carbonyltetrahydrofuran-3-yl)propionamide (150mg, 0.79mmol), potassium carbonate (109mg, 0.79mmol) was dissolved in 10mL of acetonitrile, heated to 80°C , added p-chloroaniline (101mg, 0.79mmol), after constant temperature reaction for 7h, TLC tracked the completion of the reaction, suction filtered, removed potassium carbonate, evaporated the solvent under reduced pressure, and separated by silica gel column chromatography (eluent: ethyl acetate / petroleum Ether=1 / 1) to obtain 165 mg of off-white solid, namely compound (3-b), with a yield of 74%.

Embodiment 3

[0031] Embodiment 3: Preparation of derivatives shown in general formula 3 (3-c, 3-d, 3-e, 3-f)

[0032] Compound 3-c was prepared by the method described in Example 1 with p-bromothiophenol instead of p-chlorothiophenol.

[0033] Compound 3-d was prepared by the method described in Example 1 by substituting p-bromoaniline for p-chloroaniline.

[0034] Compound 3-e was prepared by the method described in Example 1 with p-fluorothiophenol instead of p-chlorothiophenol.

[0035] Using p-fluoroaniline instead of p-chloroaniline, compound 3-f was prepared by the method described in Example 1.

[0036] The chemical structure of the partial preferred compound that the present invention synthesizes, nuclear magnetic data is as follows table 1:

[0037]

[0038]

[0039]

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PUM

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Abstract

The invention belongs to the field of medicinal chemistry and discloses benzene ring substituted N-acyl homoserine lactone compounds with bacterial quorum-sensing inhibition activity as well as a synthetic method and an application of the compounds. The preparation method is simple, mild in condition and high in yield. In-vitro activity test results prove that the benzene ring substituted N-acyl homoserine lactone compounds have an obvious inhibition effect on an LAS system and a PQS system of pseudomonas aeruginosa and can be used for preparing bacterial quorum-sensing resisting drugs, antibacterial synergists, antibacterial drugs or antitumor drugs. The general formula of the chemical structure of the compounds is shown in the specification.

Description

technical field [0001] The invention relates to a novel N-acyl homoserine lactone compound containing benzene ring substitution, a preparation method and application thereof, and belongs to the field of medicinal chemistry. Background technique [0002] During the growth of the flora, bacteria can continuously produce chemical signal molecules and secrete them into the surrounding environment. When the concentration of signal molecules reaches a certain threshold, the expression of bacteria-related genes such as bioluminescence and biofilm formation will be regulated or initiated. , Toxic gene expression, etc., to adapt to changes in the environment, this regulatory system is called the quorum sensing (QS) signaling system of bacteria. [0003] In the late 1970s, scientists discovered that the use of natural or synthetic quorum sensing regulators, including agonists or inhibitors, can interfere with the conduction of signaling systems and regulate the expression of bad bacte...

Claims

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Application Information

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IPC IPC(8): C07D307/33A61K31/365A61P31/04A61P35/00
CPCC07D307/33
Inventor 吴春丽梁永喜孔小燕冯鹏侠
Owner ZHENGZHOU UNIV
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