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4-aminoquinoline compound, and preparation method and application thereof

A technology of aminoquinolines and compounds, applied in the field of drug synthesis, to achieve excellent antibacterial activity, various types of substitutions, and simple reaction routes

Active Publication Date: 2019-10-25
CHENGDU UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the extensive use of conventional drugs, pathogenic microorganisms have developed more and more drug resistance to commonly used drugs, which makes people have to explore other quinoline compounds to ensure compounds with higher activity

Method used

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  • 4-aminoquinoline compound, and preparation method and application thereof
  • 4-aminoquinoline compound, and preparation method and application thereof
  • 4-aminoquinoline compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment one: preparation 4-aminoquinoline compound

[0033] Adopt the following steps to synthesize the 4-aminoquinoline compound among the present invention:

[0034] (1) Synthesis of intermediate 1: Mix o-aminoacetophenone and triethylamine at a molar ratio of 1:1, stir for 5 to 10 minutes, and then add formyl chloride in methylene chloride in a dropwise manner. Acyl chloride and o-aminoacetophenone are in equimolar amounts, and the type of formyl chloride is shown in Table 2; then react in a water bath at 35°C for 12 to 16 hours, then extract, dry, and purify to obtain intermediate 1;

[0035] Synthetic conditions of table 2 intermediate 1

[0036]

[0037]

[0038]

[0039] (2) Synthesis of intermediate 2: Intermediate 1 is dissolved in dioxane, and sodium hydroxide particles are added in batches to the solution under stirring conditions, and the mol ratio of added sodium hydroxide to intermediate 1 is 3: 1. Then the temperature of the solution was ra...

Embodiment 2

[0068] Embodiment two: antibacterial activity test

[0069] The specific operation of antibacterial activity test is as follows:

[0070] The first step: the activation of bacteria. The tested strains stored at low temperature were inoculated into ordinary PDA medium by streaking on the plate, and placed in a constant temperature incubator at 28°C for static culture. .

[0071] The second step: making culture medium. Take fresh potatoes, wash and peel them, weigh 200g, make small pieces, pour them into a pot, and then add 1000mL of distilled water. After the water boils, time it for 30 minutes. After the solution is cooled, filter it with multi-layer gauze, and add solvent to 1000mL to obtain potato extract. Weigh 20g of sucrose and 20g of agar, put them into the leaching solution while they are hot, stir fully to dissolve them completely, measure 180mL of leaching solution in a 300mL conical flask, repeat the operation three times to obtain three conical flasks containing...

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PUM

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Abstract

The invention discloses a 4-aminoquinoline compound, and a preparation method and application thereof. The second site of the 4-aminoquinoline compound is replaced by cyclic R-base, the 4-aminoquinoline compound is obtained by 4-step reaction of anthranilophenone and formyl chloride while the preparation, a reaction route is simple, a reaction condition is easy to be reached in a laboratory, and an operation is convenient.The 4-aminoquinoline compound has a high antibacterial activity and can be used to prepare high effective agricultural antibacterial drugs.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a 4-aminoquinoline compound and its preparation method and application. Background technique [0002] The vast majority of plant diseases come from fungal infections. From a global perspective, crop fungal diseases not only bring great economic losses to agricultural production every year, but also cause great harm to human and animal health. With the long-term and large-scale use of conventional fungicides, more and more problems have emerged, such as: the growth of drug resistance, high toxicity and high residue, and harm to non-target organisms. Therefore, it is urgent to develop new antibacterial drugs with high efficiency, low toxicity and environmental friendliness. [0003] Quinoline compounds are a class of active natural products, and a large number of studies have shown that they have antibacterial, antitumor, antiviral, and anticardiovascular diseas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/42C07D405/04A01P3/00
CPCC07D215/42C07D405/04
Inventor 杨锐秦天洪李卓霖谢佳玲何仁霄
Owner CHENGDU UNIVERSITY OF TECHNOLOGY