Nortopsentin alkaloid derivatives and their preparation and application in the prevention and treatment of diseases and insect pests

A technology of alkaloid derivatives and derivatives, which is applied in chemicals for biological control, botanical equipment and methods, applications, etc., can solve the problem of insufficient biological activity research, low natural content of Nortopsentin alkaloids, and difficult synthesis. and other problems, to achieve the effect of good insecticidal activity, good anti-plant virus and pathogen activity, and good insecticidal activity

Active Publication Date: 2021-03-30
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] Due to the low natural content of Nortopsentin alkaloids and the difficulty of synthesis, the research on biological activity is not deep enough, mainly focusing on anticancer activity, and the research on antiviral and bactericidal aspects is still in its infancy. Applications in the

Method used

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  • Nortopsentin alkaloid derivatives and their preparation and application in the prevention and treatment of diseases and insect pests
  • Nortopsentin alkaloid derivatives and their preparation and application in the prevention and treatment of diseases and insect pests
  • Nortopsentin alkaloid derivatives and their preparation and application in the prevention and treatment of diseases and insect pests

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: Synthesis of Nortopsentin alkaloid bisindole derivative structure Ia

[0035] 18: Add indole (3.51g, 30mmol) and 150mL acetonitrile to a 500mL single-necked bottle in sequence, add 60% NaH (1.44g, 42mmol) under ice-cooling, stir for about 10min, and add p-toluenesulfonyl chloride (6.27g, 33mmol), the addition was completed, and the reaction was resumed at room temperature. The reaction was monitored by TLC, and the reaction was completed in about 4 hours. with saturated NH 4 The Cl solution was quenched, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and precipitated to obtain 8.06 g of a brown solid with a yield of 99% and a melting point of 76-78°C. 1 H NMR (400MHz, CDCl 3 )δ7.99(d, J=8.4Hz, 1H), 7.76(d, J=8.4Hz, 2H), 7.56(d, J=3.6Hz, 1H), 7.52(d, J=7.6Hz, 1H) , 7.36-7.27(m, 1H), 7.24-7.18(m, 3H), 6.65(d, J=3.6Hz, 1H).

[0036] 19: Take a 500mL single-necked bottle, and put AlCl 3 (39.39g, 300mmol) was dissolved in DCM, and under ...

Embodiment 2

[0063] Embodiment 2: the assay of anti-tobacco mosaic virus activity, assay procedure is as follows:

[0064] 1. Virus purification and concentration determination:

[0065] Virus purification and concentration determination were carried out in accordance with the SOP specification for tobacco mosaic virus compiled by the Bioassay Laboratory of the Institute of Elements, Nankai University. After the crude virus extract was centrifuged twice with polyethylene glycol, the concentration was measured and refrigerated at 4°C for later use.

[0066] 2. Compound solution preparation:

[0067] After weighing, the original drug was dissolved in DMF to prepare 1×10 5μg / mL mother solution, and then diluted with 1‰ Tween 80 aqueous solution to the required concentration; Ningnanmycin preparation was directly diluted with water.

[0068] 3. In vitro effect:

[0069] Rub inoculation of leaves of Shanxi tobacco at the right age, rinse with running water, the virus concentration is 10 μg / ...

Embodiment 3

[0082] Embodiment 3: antibacterial activity test, assay procedure is as follows:

[0083] A. In vitro bactericidal test, bacterial growth rate determination method (plate method):

[0084] Dissolve a certain amount of medicine in an appropriate amount of acetone, then dilute it with an aqueous solution containing 200ug / mL emulsifier to the required concentration, then draw 1mL of the medicine solution into the petri dish, then add 9mL of medium, shake well and make 50ug / mL mL of the drug-containing plate, and a plate with 1 mL of sterilized water added as a blank control. Use a puncher with a diameter of 4mm to cut out the bacterial plate along the outer edge of the hyphae, and move it to the drug-containing plate. Each treatment was repeated three times. Place the culture dish in a constant temperature incubator at 24±1°C. After 48 hours, investigate the expanded diameters of the bacteria discs of each treatment, calculate the average value, and compare with the blank cont...

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Abstract

The invention relates to nortopsentin alkaloid derivatives I and preparation thereof, and application of the nortopsentin alkaloid derivatives I to resisting of plant viruses and pathogens and killingof insects. The nortopsentin alkaloid derivatives I in the invention show particularly excellent activity against plant viruses and insecticidal activity, can effectively inhibit tobacco mosaic viruses (TMV), and also present excellent activity against plant pathogens and insecticidal activity. Substituents in a general formula as shown in the specification are defined in the specification.

Description

technical field [0001] The invention relates to the application of Nortopsentin alkaloids in resisting plant viruses and germs and killing insects, and belongs to the technical field of agricultural protection. Background technique [0002] The ocean is a natural treasure house of human material resources. The total number of species of known marine organisms accounts for more than 80% of the earth's organisms (J Antibiot (Tokyo), 1994, 47, 1425-1433). More than 7,000 kinds of marine natural products have been isolated from sharks, corals and other marine organisms, and the newly discovered compounds are still increasing at an accelerated rate. Among the discovered compounds include terpenoids, polypeptides, steroids, polyethers, alkaloids, macrolides, polysaccharides and other compounds, about 50% have various biological activities, and more than 0.1% of the compounds have novel structures. It has remarkable activity and is very likely to be developed into a drug (Chem. Re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04C07D409/14C07D401/14A01N43/50A01P7/04A01P7/02A01P1/00A01P3/00
CPCA01N43/50C07D401/14C07D403/04C07D409/14
Inventor 汪清民冀晓霏刘玉秀王兹稳
Owner NANKAI UNIV
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