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A kind of indole compound, its synthetic method and its application

A technology for indole compounds and compounds, which is applied to indole compounds, their synthesis and application fields, can solve the problems such as no detailed reports on the antifouling activity of indole compounds, and achieves simple structure, mild reaction conditions, and high antifouling properties. The effect of fouling activity

Active Publication Date: 2021-12-17
JIANGSU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Indole antifouling agents are the most promising antifouling agents so far. The research on indole compounds as antifouling agents has made great progress. However, the current research on indole antifouling agents mainly focuses on There are indole-3-carboxaldehydes of substituents on the 3-position and the compounds of catarrhine, but there is no detailed report on the antifouling activity of indole compounds of other structures. Therefore, it is necessary to develop an economical, The method for efficiently synthesizing indole compounds will bring significant economic and social benefits to the development of this field

Method used

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  • A kind of indole compound, its synthetic method and its application
  • A kind of indole compound, its synthetic method and its application
  • A kind of indole compound, its synthetic method and its application

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Experimental program
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Effect test

Embodiment 1

[0026] Synthesis

[0027] Compound 1. Weigh 200mg of the substrate 9-methyl-1,2,3,4,9,9a-6hydro-4aH-pyrido[2,3-b]indole-4a-ol, place in 50mL to dry Add 5mL of anhydrous pyridine and stir to dissolve in a round-bottomed flask, place the system in an ice-water bath at 0°C, slowly add 0.07mL (0.72mmol) of acetic anhydride, the reaction reagent, into it dropwise, wait until the addition is complete, and move to room temperature , TLC tracking detection, after the reaction is complete, drop an appropriate amount of methanol to the reaction solution to quench the reaction, concentrate under reduced pressure to remove methanol and a small amount of pyridine, then extract with ethyl acetate for 3 times, combine the organic phases, and successively wash with saturated CuSO 4 solution washed 3 times, saturated NaCl solution washed 3 times, anhydrous NaSO 4 dry. Concentrated under reduced pressure, the crude product was separated by column chromatography (PE:EA=6:1) to obtain 216 mg ...

Embodiment 2

[0030] Synthesis

[0031] Compound 2. Colorless oil, 1 H-NMR (400MHz, CDCl 3 ), δ7.34–7.04(m,2H),6.86–6.46(m,2H),5.30(s,1H),4.45–3.63(m,1H),3.29–3.17(m,1H),2.81(ddd ,J=13.1,8.3,4.8Hz,1H),2.64(d,J=25.6Hz,3H),2.58–2.34(m,2H),1.96–1.72(m,2H),1.67–1.24(m,2H ),1.17(dt,J=10.0,7.4Hz,3H).13C NMR(100MHz,CDCl3)δ175.45(C),149.54(C),133.41(C),129.52(CH),129.33(CH), 122.04(CH), 119.06(CH), 108.34(CH), 85.36(C), 40.95(CH2), 37.20(CH3), 33.29(CH2), 27.06(CH2), 19.06, 9.60(CH3).MS(ESI (+)) calcd for C 15 h 20 N 2 o 2 [M+H] + :260.3; found: 261.0.

Embodiment 3

[0033] Synthesis

[0034] Compound 3. Pale yellow oil, 1 H-NMR (400MHz, CDCl 3), δ7.26(s,2H),6.84–6.45(m,2H),5.30(s,1H),4.44–3.62(m,1H),3.22(ddt,J=13.2,9.2,4.2Hz,1H ),3.01(s,1H),2.80(ddd,J=13.1,8.3,4.8Hz,1H),2.63(d,J=32.5Hz,3H),2.55–2.23(m,2H),1.96–1.74( m,2H),1.73–1.35(m,3H),0.96(dt,J=10.8,7.4Hz,3H).13C NMR(100MHz,CDCl3)δ174.68(C),149.54(C),133.48(C ),129.27(CH×2),122.03(CH),119.02(CH),108.30(CH),85.35(C),41.10(CH2),37.11(CH3),35.31(CH2),32.91(CH2),19.40 (CH2),18.54(CH2),13.96.(CH3).MS(ESI(+))calcd for C 16 h 22 N 2 o 2 [M+H] + :274.4; found: 275.1.

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Abstract

The present invention relates to an indole compound, its synthesis method and its application. The general formula of the indole compound has simple synthesis process and high product purity. The compound has bactericidal activity, and has high bactericidal activity against Staphylococcus aureus, Ralstonia solanaceae and Bacillus cereus , has excellent application prospects.

Description

technical field [0001] The object of the present invention is to provide an indole compound, its synthesis method and its application in antifouling aspects such as ships, wharf equipment, and offshore drilling platform pillars. Background technique [0002] Facilities below the water level such as ships and docks are in contact with seawater for a long time, and are attached by marine organisms. The attachment and deposition of marine fouling organisms in underwater facilities will lead to increased ship resistance, accelerated metal corrosion, instrument failure, and pipeline blockage. As a result, the performance and life of underwater facilities are seriously affected, causing huge economic losses. In addition, marine biofouling is also very serious in corrosion damage to marine terminal equipment, seawater cooling pipelines, power plant cooling towers, and offshore drilling platform pillars. Due to the strong vitality of marine life, the problem of marine biofouling has...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A01P1/00A61P31/04C09D5/16
CPCA61P31/04C07D471/04C09D5/1625
Inventor 朱瑞郑绍军唐冰蔡星伟杨丹丹刘苏苏滕新洁
Owner JIANGSU UNIV OF SCI & TECH
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