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Indole carbazole compound as well as preparation method and application thereof

A kind of technology of indolocarbazoles and compounds, applied in the application field of the indolocarbazoles in anti-tobacco mosaic virus

Active Publication Date: 2013-10-23
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Tobacco mosaic virus (TMV) is responsible for widespread plant diseases worldwide, and its control remains challenging

Method used

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  • Indole carbazole compound as well as preparation method and application thereof
  • Indole carbazole compound as well as preparation method and application thereof
  • Indole carbazole compound as well as preparation method and application thereof

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preparation example Construction

[0038] On the other hand, the present invention provides a kind of preparation method of indolecarbazole compound, comprising:

[0039] (1) Will replace or not replace in me 2 In the presence of NH and EtOH, the reaction obtains the first product;

[0040] (2) the first product that step (1) obtains and NaBH 4 , BF 3 Et 2 O is contacted with DME to obtain a second product;

[0041] (3) the second product that step (2) obtains and The reaction was carried out in the presence of AcOH.

[0042] In the method of the present invention, the reaction conditions in step (1) include: temperature 15-30°C, time 22-26h.

[0043] In the method of the present invention, the contact conditions in step (2) include: temperature 15-30°C, time 1-3h.

[0044] In the method of the present invention, the reaction conditions of step (3) include: a temperature of 90-100°C, and the time varies according to X, for example, X is -O-, and the reaction time is 45-50h; X is -NH, and the reaction ...

Embodiment

[0064] The following compounds were prepared:

[0065]

[0066] Compound 1 (3,3'-biindole):

[0067] Indole (11.72g, 100mmol), isatin (14.71g, 100mmol), 40% dimethylamine aqueous solution (1mL) and 150mL ethanol were heated and stirred at 45°C in a 250mL flask for 1 hour, then stirred at room temperature overnight. Then, water was added to the system until the system became cloudy (150-200mL water). After a few minutes, a gray solid was precipitated, and the intermediate (23.78g, 90%) was obtained after suction filtration and drying, which was directly used for the next reaction. Into a 250 mL flask was charged 13.22 g of the intermediate compound (50 mmol), sodium boro-hydride (5.68 g, 150 mmol) and 75 mL of ethylene glycol dimethyl ether. Then, a solution of boron trifluoride diethyl ether (28.38 g, 200 mmol) in 25 mL of ethylene glycol dimethyl ether was slowly dropped into the system using a constant pressure dropping funnel, and the addition was completed in about 30...

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Abstract

The invention discloses an indole carbazole compound which is characterized by having a structure as shown in a formula I, a formula II, a formula III or a formula IV described in the specification. The indole carbazole has anti-TMV (tobacco mosaic virus) activity.

Description

technical field [0001] The invention relates to an indolecarbazole compound, a preparation method thereof, and an application of the indolecarbazole compound in resisting tobacco mosaic virus (TMV). Background technique [0002] Tobacco mosaic virus (TMV) is responsible for widespread plant diseases worldwide, and its control remains challenging. It is a widely studied model virus, and it is also a plant virus with strong infectivity and great harm to agricultural production. Tobacco mosaic virus contains a single RNA positive strand of 6395 nucleotides, and the RNA is wrapped by 2130 identical capsid protein subunits, each subunit contains 158 amino acid residues. The assembly reaction of the virus begins with the specific recognition of a special sequence on the TMV RNA by the disc aggregates of the capsid protein, which is called the assembly origin of TMV RNA. The general process of TMV assembly is the 20S disk aggregates of the RNA assembly initiation sequence binding...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D487/14C07D491/147C07D495/14A01N43/90A01P1/00
Inventor 席真陈红军陈文彬
Owner NANKAI UNIV
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