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Synthesis and application of thiourea compound with antibacterial activity

A technology of antibacterial activity and compounds, which is applied in the synthesis and application of thiourea compounds with antibacterial activity, can solve the problems of frequent drug resistance of pathogens, and achieve high yield, high antibacterial activity, and good antibacterial activity.

Active Publication Date: 2017-11-07
SOUTHWEAT UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But at the same time, the widespread use of thiazole antibacterial drugs has led to the frequent occurrence of drug resistance of pathogens, and it is urgent to develop new structural thiazole compounds

Method used

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  • Synthesis and application of thiourea compound with antibacterial activity
  • Synthesis and application of thiourea compound with antibacterial activity
  • Synthesis and application of thiourea compound with antibacterial activity

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Experimental program
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Embodiment

[0022] 1. 1-(Benzo[d]thiazol-2-yl)-3-(isoquinolin-5-ylmethyl)thiourea, its structural formula is:

[0023]

[0024] Preparation method: Dissolve 5-methylisothiocyanate-substituted isoquinoline (1 g, 4.99 mmol) in anhydrous dichloromethane (20 mL), add benzothiazol-2-amine (0.83 g, 5.49 mmol) and diisopropylethylamine (0.6 mL), stirred at room temperature for 3h. After the reaction was detected by TLC, it was diluted with ethyl acetate, washed twice with 5% dilute hydrochloric acid, twice with saturated sodium carbonate, twice with water, and once with saturated brine. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure and separated by silica gel column chromatography to obtain 1.4 g of the target product with a yield of 81%. 1 H NMR (500 MHz, CDCl 3 ): δ 9.24 (d, J = 1.4 Hz, 1H), 8.59 (d, J =7.5 Hz, 1H), 7.88 – 7.81 (m, 2H), 7.72 (dd, J = 7.5, 1.5 Hz, 1H), 7.66 (dd, J = 7.5, 1.6 Hz, 1H), 7.59 – 7.50 (m, 2H), 7.19 (td, J ...

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Abstract

The invention prepares a thiourea compound. The thiourea compound is prepared by the following steps: dissolving a substrate 5-isothiocyanate methyl isoquinoline into anhydrous dichloromethane or anhydrous tetrahydrofuran, adding different aromatic ring substituted thiazole compounds which is equivalent to 1.1 times the weight of the substrate and diisopropylethylamine which is equivalent to 3-5 times the weight of the substrate, stirring at the room temperature for 3-5 hours; after TLC detection reaction is finished, adding ethyl acetate for dilution, washing twice with 5% diluted hydrochloric acid, washing twice with saturated sodium carbonate, washing twice with water, and washing with saturated table salt water; and drying an organic phase with anhydrous sodium sulfate, carrying out reduced pressure concentration, separating through silica gel column chromatography, so as to obtain the target product. The compound has application values in antibacterial aspects and particularly has better antibacterial effects on inhibiting gram-positive bacteria such as staphylococcus aureus than a known antibacterial drug, namely penbritin, so that the thiourea compound can be taken as a novel antibacterial drug to be researched and utilized.

Description

technical field [0001] The invention relates to a class of thiourea compounds, a preparation method thereof and the antibacterial application of the compounds. Background technique [0002] In recent years, research on antibiotics has developed rapidly, and they have played an active role in applications such as antifungal, antibacterial, antitumor, and antiinfection. With the widespread use of antibiotics in clinical practice and the emergence of problems such as antibiotic abuse, microbial resistance has increased year by year. At the same time, some non-pathogenic bacteria have also become opportunistic pathogens, causing new threats clinically, so it is urgent to screen new types of antibiotics with new structures and new antibacterial mechanisms. [0003] Thiazole compounds can bind to various targets such as enzymes and receptors in organisms to exhibit a variety of biological activities, covering almost the entire field of pharmaceutical applications. A large number...

Claims

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Application Information

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IPC IPC(8): C07D417/14A61P31/04
CPCC07D417/14
Inventor 李良春郑仁林孙荣琴黄毅陈红英
Owner SOUTHWEAT UNIV OF SCI & TECH
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