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Chiral indole compound and preparation method and ship antifouling application thereof

A compound and indole technology, applied in the field of chiral indole compounds, their preparation and ship antifouling application, can solve the problems of increasing cost, polluting the environment, waste of raw materials, etc.

Active Publication Date: 2021-04-30
JIANGSU UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, a large amount of waste of raw materials has been caused, the cost has been increased, and the environment has also been polluted.

Method used

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  • Chiral indole compound and preparation method and ship antifouling application thereof
  • Chiral indole compound and preparation method and ship antifouling application thereof
  • Chiral indole compound and preparation method and ship antifouling application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Synthesis of intermediate compound 1

[0032]

[0033] Weigh 1.47g (10mmol) of 3-methyloxindole in a 250mL dry round bottom flask, add 30mL DCM, stir at room temperature for 15min to dissolve completely, place the reaction solution in an ice bath at 0°C, and then use Slowly add 100mL of Boc anhydride dropwise into the constant pressure funnel, and after the dropwise addition is complete, move the reaction solution to room temperature and stir for 30min. Add 50mL water to dilute, use anhydrous K 2 CO 3 or anhydrous Na 2 CO 3 The pH value of the solid is adjusted, and the pH value of the solution is detected while stirring, and the pH value of the solution is adjusted between 7 and 8. The whole system was moved to room temperature, extracted with ethyl acetate (3×100 mL), combined the organic phases, washed with saturated sodium chloride (3×50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 2.24 g of compound 1 (91% ...

Embodiment 2

[0052] Embodiment 2: Determination of bactericidal activity to synthetic compounds

[0053] The antibacterial activity of target product 10 against Staphylococcus aureus and Escherichia coli was determined by microdilution method. All strains were purchased from China General Microorganism Culture Collection Center.

[0054] Using the test tube double dilution method, take a sterilized test tube added with 2 mL of liquid medium, use the test tube inoculated without the test compound as the positive control, and use the test tube without the test compound and inoculated as the negative control. The initial mass concentration of the drug is 1g / L, which is diluted by two times successively and mixed evenly. Add 200 μL of bacterial suspension to each test tube to make the final bacterial concentration 10 4 ~10 5 cfu / mL (cfu is colony forming unit, 1cfu refers to a single colony formed on the agar plate after cultivation). After 24 hours of shaking culture, the minimum inhibito...

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PUM

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Abstract

The invention relates to a chiral 3-cyclic indole compound shown as a formula (I). The compound is prepared by the following steps: using 3-methyl hydroxyindole as a raw material, obtaining a chiral intermediate under the action of a chiral catalyst, and carrying out four-step reaction to obtain the chiral compound with antifouling potential, thereby enhancing the atom utilization ratio. The compound is simple in process and high in product purity, has very high bactericidal activity on escherichia coli and staphylococcus aureus, and has an excellent ship antifouling application prospect.

Description

technical field [0001] The object of the present invention is to provide a novel chiral 3-ring indole compound, its preparation method and its application in ship antifouling. Background technique [0002] Marine biofouling refers to the phenomenon that micro-fouling organisms and macro-fouling organisms in seawater adhere to and accumulate on the surface of substrate soaked in seawater, which has adverse effects on human production activities and marine ecological environment. Marine biofouling has long been a major problem in the shipping industry, costing approximately US$200 billion a year. Marine biofouling not only causes additional fuel consumption, reduces the service life of ships, but also increases carbon dioxide emissions. According to Lloyd's Register of Shipping, the world's annual increase in fuel consumption by 28% will result in an additional 250 million tons of carbon dioxide emissions. [0003] At present, the most important antifouling method is to appl...

Claims

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Application Information

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IPC IPC(8): C07D487/04A01N43/90A01P3/00A01P1/00
CPCC07D487/04A01N43/90
Inventor 郑绍军林传颂武文斌谈祎戴慧慧方越朱瑞
Owner JIANGSU UNIV OF SCI & TECH
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