N-acyl-homoserine lactones substituted by benzo-heterocycle and preparation method and application thereof

A technology for chloroacylating homoserine lactone and acyl homoserine, which is applied to medical preparations containing active ingredients, organic chemistry, drug combinations, etc., and achieves the effects of simple preparation method, mild conditions and high yield

Active Publication Date: 2017-03-22
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 benzoheterocyclic structure, study its quorum sensing inhibitory activity, and further study new antibacterial quorum sensi

Method used

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  • N-acyl-homoserine lactones substituted by benzo-heterocycle and preparation method and application thereof
  • N-acyl-homoserine lactones substituted by benzo-heterocycle and preparation method and application thereof
  • N-acyl-homoserine lactones substituted by benzo-heterocycle and 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)acetamide (150mg, 0.84mmol), potassium carbonate (116mg, 0.84mmol) was dissolved in 10mL of acetonitrile, heated to 80°C , added 2-mercaptobenzothiazole (140mg, 0.84mmol), after constant temperature reaction for 3h, TLC followed the completion of the reaction, filtered with suction, removed potassium carbonate, evaporated the solvent under reduced pressure, and separated by silica gel column chromatography (eluent: ethyl acetate Ester / petroleum ether=2 / 1) to obtain 191 mg of off-white solid, namely compound (3-a), with a yield of 74%.

Embodiment 2

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

[0030] Compound (S)-2-chloro-N-(2-carbonyltetrahydrofuran-3-yl)acetamide (150mg, 0.84mmol), potassium carbonate (116mg, 0.84mmol) was dissolved in 10mL of acetonitrile, heated to 80°C , added 2-mercaptobenzoxazole (127mg, 0.84mmol), after constant temperature reaction for 4h, TLC followed the completion of the reaction, filtered with suction, removed potassium carbonate, evaporated the solvent under reduced pressure, and separated by silica gel column chromatography (eluent: acetic acid Ethyl ester / petroleum ether=2 / 1) to obtain 179 mg of off-white solid, namely compound (3-b), with a yield of 73%.

Embodiment 3

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

[0032] Using 2-hydroxybenzothiazole instead of 2-mercaptobenzothiazole, compound 3-c was prepared in the same manner as in Example 1.

[0033] Using 2-hydroxybenzoxazole instead of 2-mercaptobenzoxazole, compound 3-d was prepared in the same manner as in Example 1.

[0034] Adopt compound (S)-2-chloro-N-(2-carbonyltetrahydrofuran-3-yl)propionamide to replace compound (S)-2-chloro-N-(2-carbonyltetrahydrofuran-3-yl)acetamide, with Compound 3-e was prepared by the same method as Example 1.

[0035] Using compound (S)-2-chloro-N-(2-carbonyltetrahydrofuran-3-yl)propanamide instead of compound (S)-2-chloro-N-(2-carbonyltetrahydrofuran-3-yl)acetamide, Compound 3-f was prepared in the same manner as in Example 2.

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

[0037]

[0038] ...

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Abstract

The invention belongs to the field of medicinal chemistry, and discloses N-acyl-homoserine lactones substituted by benzo-heterocycle with bacterial quorum sensing inhibitory activity and a synthetic method and application thereof. The preparation method is simple, the conditions are mild and the yield is high. In vitro activity test results show that the N-acyl-homoserine lactones substituted by benzo-heterocycle can have an obvious inhibiting effect on a pseudomonas aeruginosa LAS system and a PQS system and can be applied to preparation of anti-bacterial quorum sensing and antimicrobial synergists and antibacterial or antitumor drugs. The chemical general molecular formula of the N-acyl-homoserine lactones substituted by benzo-heterocycle is as follows (please see the specification for the formula).

Description

technical field [0001] The invention relates to a novel N-acyl homoserine lactone compound containing benzoheterocycle 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 b...

Claims

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Application Information

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IPC IPC(8): C07D417/12C07D413/12A61K31/428A61K31/423A61P31/04A61P35/00
CPCC07D413/12C07D417/12
Inventor 吴春丽梁永喜孔小燕冯鹏侠
Owner ZHENGZHOU UNIV
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