Carbazole alkaloid derivative and preparation method and application thereof

A technology for carbazole alkaloids and derivatives, which is applied in the field of carbazole alkaloid derivatives and their preparation, can solve the problems of difficulty in preventing and controlling plant virus diseases, lack of an immune metabolism system, affecting the yield and quality of tobacco leaves, and achieves good resistance to plants. The effect of virus activity, simple preparation method and obvious application prospect

Active Publication Date: 2021-02-19
HUBEI BIOPESTICIDE ENG RES CENT +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tobacco mosaic virus (TMV) is also one of the most harmful plant viruses to commercial crops. It can infect more than 400 kinds of plants in 36 families. It is distributed in major tobacco producing areas all over the world, seriously affecting the yield and quality of tobacco leaves. , bringing huge economic losses to the tobacco industry
Since the virus is absolutely parasitic in the host cell, and the host plant itself lacks a complete immune metabolism system, once the plant is infected by the virus, it is often infected for life, so the prevention and treatment of plant virus diseases is always difficult.
So far, only a few commercial agents are used to prevent and control plant virus diseases, such as Ningnanmycin, ribavirin, emodin, etc., and many antiviral agents are far from satisfactory control effects. The occurrence of plant virus diseases is becoming more and more serious, and the anti-plant virus agents are still in short supply. It is very urgent to carry out research on anti-plant virus agents. The research and development of new plant virus inhibitors with high efficiency, low toxicity and selectivity has become an important task at present. research work

Method used

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  • Carbazole alkaloid derivative and preparation method and application thereof
  • Carbazole alkaloid derivative and preparation method and application thereof
  • Carbazole alkaloid derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Numbering is the preparation of the compound of I2 in table 1, and its reaction path is:

[0031]

[0032] Its preparation method comprises the following steps:

[0033] 1) Dissolve indole (10mmol), bromoacetaldehyde diethyl acetal (10mmol), and ethyl acetoacetate (10mmol) in organic solvent ethanol (30mL), then add ZnCl 2 (1.0 mol), the above reaction solution was stirred and reacted at 60° C. for 2 h in a reactor equipped with magnetic stirring.

[0034] 2) Intermediate 2a (5.0 mmol) was dissolved in KOH (15.0 mmol) in EtOH / H 2 O (3:1) solution (20 mL), stirred at 70°C for 6 h, then acidified by adding dilute hydrochloric acid.

[0035] 3) Intermediate 3a (3 mmol) was dissolved in 15 mL of dry DMF, then HATU (3.3 mmol) and DIPEA (15 mmol) were added in sequence, and the reaction solution was reacted at room temperature for 8 h. The target compound I2 was obtained.

[0036] Spectral data of target compound I2: 1 H NMR (600MHz, DMSO-d 6 ,25℃)δ=11.26(s,1H),10.84...

Embodiment 2

[0038] Numbering is the preparation of the compound of I11 in table 1, and its reaction path is:

[0039]

[0040] Its preparation method comprises the following steps:

[0041] 1) Dissolve indole (10mmol), bromoacetaldehyde diethyl acetal (10mmol) and ethyl acetoacetate (10mmol) in organic solvent acetonitrile (30mL), then add AlCl 3 (1.0 mol), the above reaction solution was stirred and reacted at 50° C. for 2 hours in a reactor equipped with magnetic stirring.

[0042] 2) Intermediate 2a (5.0 mmol) was dissolved in 20 mL of ethanol, hydrazine hydrate (25 mmol) was added, and the above reaction solution was stirred and reacted at 80° C. for 6 hours in a reactor equipped with magnetic stirring.

[0043] 3) Intermediate 4a (2.0 mmol) and 3,4-dimethoxybenzaldehyde (2.0 mmol) were dissolved in ethanol (10 mL) respectively, and heated to reflux overnight to obtain the target compound I11.

[0044] Spectral data of target compound I11: 1 H NMR (600MHz, DMSO-d 6 ,25℃)δ=11.66...

Embodiment 3

[0046] Numbering is the preparation of the compound of I12 in table 1, and its reaction route is:

[0047]

[0048] Its preparation method comprises the following steps:

[0049] 1) Dissolve indole (10mmol), bromoacetaldehyde diethyl acetal (10mmol) and ethyl acetoacetate (10mmol) in the organic solvent toluene (30mL), then add HAc (0.5mL), and dissolve the above reaction solution in the In a reactor with magnetic stirring, the reaction was stirred at 60° C. for 4 h.

[0050] 2) Intermediate 2a (5.0 mmol) was dissolved in 20 mL of acetonitrile, hydrazine hydrate (30.0 mmol) was added, and the above reaction solution was reacted at 80° C. for 6 h in a reactor equipped with magnetic stirring.

[0051] 3) Intermediate 4a (2.0 mmol) and 3,4,5-trimethoxybenzaldehyde (2.0 mmol) were dissolved in ethanol (10 mL) respectively, and heated to reflux overnight to obtain the target compound I12.

[0052] Spectral data of target compound I12: 1 H NMR (600MHz, DMSO-d 6,25℃)δ=11.79(s,...

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PUM

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Abstract

The invention discloses a carbazole alkaloid derivative and a preparation method and application thereof, and the structural formula of the carbazole alkaloid derivative is shown in the specification.Practice proves that the compound has good anti-plant virus activity, the preparation method is simple, raw materials are cheap and easy to obtain, and the carbazole alkaloid derivative is suitable for industrial amplification; along with the increase of the drug resistance of the existing anti-plant virus drugs, the compound can be used as an efficient substitute product for preparing active ingredients of a novel plant virus inhibitor, is suitable for preparing anti-plant virus drugs and active ingredients thereof, and has obvious application prospects in the related fields of biological drug technologies and the like.

Description

technical field [0001] The invention belongs to the field of pharmaceutical biotechnology, and in particular relates to a carbazole alkaloid derivative and its preparation method and application. Background technique [0002] Plant virus disease is a kind of important crop disease, which occurs in rice, tobacco, vegetables and other crops and economic crops, and its frequency of occurrence is high, often causing huge economic losses. The research and prevention of plant virus diseases has always been a major problem in agricultural production in the world. The vast majority of commercial crops have been reduced in yield or quality due to the damage of plant viruses. The economic losses of crops caused by plant viruses in the world are as high as tens of billions of dollars every year. The dollar is known as "plant cancer". Southern rice black-streaked dwarf disease (SRBSDV) is a new rice virus disease discovered in southern China. It can spread rapidly in rice-producing are...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88A01N43/38A01N25/04A01N25/14A01P1/00
CPCC07D209/88A01N43/38A01N25/04A01N25/14
Inventor 柯少勇位灯国黄文博张宪鹏王开梅石丽桥刘思思李峰
Owner HUBEI BIOPESTICIDE ENG RES CENT
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