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Hexahydropyrrolo-indole compound as well as preparation method and application thereof

A technology of hexahydropyrrole and compound, which is applied in organic chemistry, biocide-containing paint, antifouling/underwater coating, etc., can solve the problem that there are no detailed reports on the antifouling activity of indole compounds, and achieve novel structure , short synthesis steps and mild reaction conditions

Inactive Publication Date: 2017-04-26
MARINE EQUIP & TECH INST JIANGSU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The research on indole compounds as antifouling agents has made great progress. However, the current research on indole antifouling agents mainly focuses on indole-3-carboxaldehydes and anophylline with substituents at the 3-position. However, there are no detailed reports on the antifouling activity of indole compounds with other structures

Method used

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  • Hexahydropyrrolo-indole compound as well as preparation method and application thereof
  • Hexahydropyrrolo-indole compound as well as preparation method and application thereof
  • Hexahydropyrrolo-indole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of Hexahydropyrroloindoles. This example provides the synthesis steps of the hexahydropyrroloindole compounds, specifically as follows:

[0037] 1. Synthesis of oxindole-3-acetonitrile

[0038]

[0039] Weigh 3.12g (20mmol) of indole-3-acetonitrile in a 250mL dry round bottom flask, add 30mL DMSO, 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 150 mL of concentrated hydrochloric acid (37% HCl, V DMSO :V HCl =1:5), after the dropwise addition was complete, the reaction solution was moved to room temperature and stirred for 30 min, and TLC (PE:EA=4:1) detected that the reaction of the raw materials was complete. The reaction solution was placed in an ice bath at 0°C, diluted with 50 mL of water, and washed with anhydrous K 2 CO 3 or anhydrous Na 2 CO 3The pH value of the solid is adjusted, and the pH value of the solution is detected while stirring, and the pH value ...

Embodiment 2

[0056] Determination of the fungicidal activity of hexahydropyrroloindole compounds.

[0057] Determination of N-formic acid methyl hexahydropyrrole-5-formic acid methyl ester-[2,3]-N-triazole (N-butyl)-indole on Staphylococcus aureus (staphylococcus aureus) and Bacteriostatic activity of Escherichia coli. All strains used were purchased from the China General Microorganism Culture Collection Center.

[0058] 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 a certain mass concentration of bacterial suspension to each test tube, so that the final bacterial concentration is 10 4 ~10 5 cfu / mL (cfu is the colony forming unit, 1cfu ...

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Abstract

The invention belongs to the technical field of marine antifouling, and discloses a hexahydropyrrolo-indole compound of a formula (I) as shown in the specification; in the formula, R1 and R2 represent single-substituted or multi-substituted benzyl; R1 and R2 can be identical substituent groups. A synthesis route comprises that indole-3-acetonitrile is adopted as an initial synthesis raw material. A method for preparing the hexahydropyrrolo-indole compound, which is disclosed by the invention, has the advantages of being high in yield, easy to separate and the like. The compound has inhibition functions of different grades to staphylococcus aureus and escherichia coli, and can be developed as an antiflouring agent with potential application values in ship antiflouring.

Description

technical field [0001] The invention belongs to the technical field of ship antifouling, and relates to a class of novel ship antifouling compounds, in particular to a class of hexahydropyrroloindole compounds. The invention also provides a synthesis method of this type of compound and its application in ship antifouling. Background technique [0002] Ships often suffer from the surface attachment of seaweed, barnacles and other marine organisms during ocean travel, which is called biofouling. Biofouling will increase the weight and navigation resistance of the ship, thereby increasing fuel consumption; it will also greatly accelerate the corrosion of the bottom steel plate and reduce the service life of the ship. In order to reduce the hazards of fouling, many countries have carried out research on environmentally friendly ship antifouling technology, and the application of antifouling paint has become the most widely used method. Applying antifouling paint has outstandin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09D7/12C09D5/16
CPCC07D487/04C09D5/1625C09D7/63
Inventor 郑绍军刘静李蕊蕊杨丹丹白红进张继文
Owner MARINE EQUIP & TECH INST JIANGSU UNIV OF SCI & TECH