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Tryptanthrin derivative and preparation thereof and application of tryptanthrin derivative in prevention and treatment of plant viruses and pathogenic bacteria

A technology of tryptanthrin and derivatives, applied in the fields of chemicals for biological control, botany equipment and methods, applications, etc.

Active Publication Date: 2021-06-25
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there is no application of this type of compound in the prevention and treatment of plant virus and bacterial diseases.

Method used

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  • Tryptanthrin derivative and preparation thereof and application of tryptanthrin derivative in prevention and treatment of plant viruses and pathogenic bacteria
  • Tryptanthrin derivative and preparation thereof and application of tryptanthrin derivative in prevention and treatment of plant viruses and pathogenic bacteria
  • Tryptanthrin derivative and preparation thereof and application of tryptanthrin derivative in prevention and treatment of plant viruses and pathogenic bacteria

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: the synthesis of tryptanthrin derivative I-1

[0022] The first step, the synthesis of 8-methoxytryptanthrin (3). In a 100mL round bottom flask, add 5-methoxyisatin (1) (1.0g, 5.6mmol), isatoic anhydride (2) (0.92g, 5.6mmol), triethylamine (4.0mL, 28.0mmol) and toluene (40mL), heated to reflux at 110°C for six hours, TLC monitored the completion of the reaction, and suction filtered to obtain a yellow solid (product), the filtrate was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and suction filtered. Precipitation under reduced pressure, column chromatography (V (petroleum ether): V (ethyl acetate) = 1: 1), a yellow solid was obtained, and the products were combined to obtain a total of 1.1 g of the product, with a yield of 73% and a melting point of 270-272°C . 1 H NMR (400MHz, DMSO-d6) δ8.37(d, J=8.5Hz, 1H), 8.30(d, J=7.9Hz, 1H), 7.93(d, J=3.7Hz, 2H), 7.73(dt , J=8.2, 4.2Hz, 1H), 7.45-7.39(m, 2H), 3.87(...

Embodiment 2

[0024] Example 2: Synthesis of tryptanthrin derivative I-2.

[0025] The first step: the synthesis of tryptanthrin (5). In a 100 mL round bottom flask was added isatin (4) (1.0 g, 6.8 mmol), isatoic anhydride (2) (1.12 g, 6.8 mmol), triethylamine (4.8 mL, 34 mmol) and toluene (40 mL) , heated to reflux at 110°C for six hours, TLC monitored that the reaction was complete, suction filtered to obtain a yellow solid (product), the filtrate was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, suction filtered, and precipitated under reduced pressure, Column chromatography (V (petroleum ether): V (ethyl acetate) = 1: 1) gave a yellow solid. The products were combined to obtain 1.6 g of the product in a yield of 95%. The melting point was 267-269°C. 1 H NMR (400MHz, DMSO-d6) δ8.47(d, J=7.9Hz, 1H), 8.31(d, J=7.8Hz, 1H), 7.94(d, J=3.8Hz, 2H), 7.91-7.84 (m, 2H), 7.78-7.69(m, 1H), 7.48(t, J=7.5Hz, 1H). 13 C NMR (100MHz, DMSO-d6) δ 182.4, 15...

Embodiment 3

[0027] Example 3: Synthesis of tryptanthrin derivative I-3.

[0028] Dissolve tryptanthrin (5) (1.0 g, 4.0 mmol) in 50 mL of anhydrous methanol, gradually add 2-hydrazinopyridine (6) (0.66 g, 6.0 mmol), and heat to reflux at 70°C for 6 h under argon protection. After the reaction was completed, it was cooled to room temperature, suction filtered, and the filter cake was washed with methanol to obtain 0.7 g of a red solid with a yield of 52% and a melting point of 214-216°C. 1 H NMR (400MHz, CDCl 3 )δ13.40(s, 1H), 8.59(d, J=8.0Hz, 1H), 8.46(d, J=7.7Hz, 1H), 8.36(d, J=4.5Hz, 1H), 7.99(d, J=8.1Hz, 1H), 7.90(d, J=7.5Hz, 1H), 7.82(t, J=7.6Hz, 1H), 7.78-7.73(m, 1H), 7.72-7.68(m, 1H), 7.58(t, J=7.5Hz, 1H), 7.48(t, J=7.7Hz, 1H), 7.39(t, J=7.5Hz, 1H), 7.01(t, 1H). 13 C NMR (100MHz, CDCl 3C 20 h 13 N 5 O[M+H] + 340.1193, found 340.1195.

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Abstract

The invention relates to tryptanthrin derivatives I-1 to I-7, and a preparation method thereof and application of the tryptanthrin derivatives I-1 to I-7 in prevention and treatment of plant viruses and pathogenic bacteria. The tryptanthrin derivatives I-1 to I-7 provided by the invention show anti-plant virus activity, can well inhibit tobacco mosaic virus, also show broad-spectrum anti-plant germ activity, and have outstanding inhibitory activity on apple ring spot bacteria.

Description

technical field [0001] The invention relates to a tryptanthrin derivative and its preparation and application in the prevention and treatment of plant virus and bacterial diseases, belonging to the technical field of agricultural protection. Background technique [0002] Nitrogen-containing heterocycles have always played an important role in the creation of new drugs. In the process of finding active lead compounds, designing and synthesizing nitrogen-containing heterocycles is one of the important ways. Among nitrogen-containing heterocyclic compounds, compounds containing indole skeletons usually have a wide range of biological activities and low toxicity to humans and the environment, such as tryptanthrin (structural formula 1). [0003] [0004] Tryptanthrin is composed of indole-fused quinazoline rings. It is the main component of the traditional Chinese medicine Qingdai and Daqingye. It has a wide range of biological activities such as anti-cancer, anti-human bact...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P3/00A01P1/00
CPCC07D487/04A01N43/90
Inventor 汪清民郝亚男刘玉秀王兹稳宋红健李永强
Owner NANKAI UNIV
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