A kind of indole methyl aniline compound and application thereof

A kind of technology of indole methyl aniline and compound, which is applied in the field of substituted 4-methyl)-N-methyl aniline compounds, can solve the problems such as structure and biological activity that have not been reported in literature and the like

Inactive Publication Date: 2021-04-23
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The substituted 4-((1) designed and synthesized by the present invention H -Indol-3-yl)methyl)- N -Methylaniline compounds, the structure and biological activity of which have not been reported in the literature

Method used

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  • A kind of indole methyl aniline compound and application thereof
  • A kind of indole methyl aniline compound and application thereof
  • A kind of indole methyl aniline compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1 Derivative Ia ((R 1 )n = N -Methyl-5-bromo, (R 2 )m = H, R 3 = methyl) synthesis

[0028] weigh N -Methyl-5-bromoindole (0.5 mmol), N , N -Dimethylaniline (4.0 eq.) and 1.5 mol% of RoseBengal were placed in a 25 mL Schlenk reaction tube, and then 5 mL of tetrahydrofuran was added, under the state of air, placed under a 15 W LED white light to react, and stirred at room temperature for the reaction, After 24 h, the reaction was completed, the solvent was removed, and the concentrated solution was separated by column chromatography (petroleum ether / ethyl acetate=15:1, V / V) to obtain a yellow oily liquid, namely derivative Ia. Yield 61%.

[0029] of the compound 1 H NMR, 1 C NMR and ESI-HRMS analysis data as follows,

[0030] 1 H NMR (CDCl 3 , 500 MHz) δ 7.74 (d, J = 2.0 Hz, 1H), 7.33 (dd, J = 8.5,2.0 Hz, 1H), 7.20 (d, J = 8.5, 2 H), 7.17 (d, J = 9.0 Hz, 1 H), 6.77 (s, 2H), 6.76 (t, J = 2.5 Hz, 1H), 4.01 (s, 2H), 3.71 (s, 3H), 2.98 (s, 6H...

Embodiment 2

[0031] Embodiment 2 Derivatives Ib ((R 1 )n = N -Methyl-5-chloro, (R 2 )m = H, R 3 = methyl) synthesis

[0032] weigh N -Methyl-5-chloroindole (0.5 mmol), N , N -Dimethylaniline (5.5 eq.) and 3.5 mol% Rhodamine B were placed in a 25 mL Schlenk reaction tube, then 5 mL of chloroform was added, under the state of air, placed under a 20 WLED white light to react, and stirred at room temperature The reaction was tracked and monitored by TLC. After 36 h, the reaction was completed, the solvent was removed, and the concentrated solution was separated by column chromatography (petroleum ether / ethyl acetate=10: 1, V / V) to obtain a yellow oily liquid, namely derivative Ib. Yield 51%.

[0033] of the compound 1 H NMR, 1 C NMR and ESI-HRMS analysis data as follows,

[0034] 1 H NMR (CDCl 3 , 500 MHz) δ 7.56 (d, J = 1.0 Hz, 1H), 7.25-7.2 (m, 3H),6.18 (s, 1H), 6.79 (s, 1H), 6.75 (d, J = 9.0 Hz, 2H), 4.00 (s, 2H), 3.72 (s,3H), 2.96 (s, 6H); 13 C NMR (CDCl 3 C 18 h 20 N ...

Embodiment 3

[0035] Example 3 Derivatives Ic ((R 1 )n = N , 5-Dimethyl, (R 2 )m = H, R 3 = methyl) synthesis

[0036] weigh N , 5-Dimethylindole (0.5 mmol), N , N -Dimethylaniline (5.5 eq.) and 2.0 mol% Eosin B were placed in a 25 mL Schlenk reaction tube, then 6 mL of acetonitrile and 1 mL of water were added, and the reaction was carried out under a 15 W LED white light under the condition of air ventilation, at room temperature The reaction was stirred at lower temperature and followed and monitored by TLC. After 24 h, the reaction was completed, the solvent was removed, and the concentrated solution was separated by column chromatography (petroleum ether / ethyl acetate=10: 1, V / V) to obtain wine red oily liquid, namely derivative Object Ic. The yield is 68%.

[0037] of the compound 1 H NMR, 1 C NMR and ESI-HRMS analysis data as follows,

[0038] 1 H NMR (CDCl 3 , 500 MHz) δ 7.36 (s, 1H), 7.17-7.19 (d, J = 8.5 Hz, 3H),7.05 (dd, J = 8.0, 1.5 Hz, 1H), 6.74-6.72 (d, J = ...

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Abstract

The invention discloses an indolemethylaniline compound and its application, specifically a substituted 4‑((1 H ‑indol‑3‑yl)methyl)‑ N ‑Methylaniline compounds and their applications. The compound is simple to prepare and exhibits good antifungal activity. The present invention adopts the method of potato agar containing medicine (PDA) to carry out the fungal anthracnose oxysporum and strawberry anthracnose to the synthesized compound 、 Botrytis cinerea 、 The bactericidal activity assay of Fusarium oxysporum, all compounds of embodiment 1~14 are to anthracnose oxysporum, strawberry anthracnose 、 Botrytis cinerea all showed certain inhibitory activity, and some compounds also had certain inhibitory effect on Fusarium oxysporum.

Description

technical field [0001] The present invention relates to a kind of indolemethylaniline compound and application thereof, specifically substituted 4-((1 H -Indol-3-yl)methyl)- N -Methylaniline compounds and applications thereof. Background technique [0002] Indole structures widely exist in natural products and bioactive molecules, and are important intermediates in organic synthesis. Due to the indole structure has antitumor (J. Med. Chem. 2015, 58, 3209), antibacterial (Med. Chem. Res. 2018, 27, 1624; Organic Chemistry, 2016, 36, 158), herbicidal (Organic Chemistry, 2010, 30(8): 1207-1211), anticonvulsant (Pharma Chem. 2012, 6, 2438), anti-inflammatory (Int. Immunopharmacol. 2011, 11, 1816), anti-algae (Acta Chem. 2008, 66(22 ): 2507) and other extensive physiological activities, it has become one of the important precursors for the creation of new drugs. Some indole compounds have been successfully developed into clinical drugs, such as reserpine (Reserpine), active na...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/14A01N43/38A01P1/00A01P3/00
CPCA01N43/38C07D209/14
Inventor 翁建全章俊辉周智勇周亮谭成侠刘幸海
Owner ZHEJIANG UNIV OF TECH
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