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Kealiinine derivative, preparation thereof and application of the derivative in resisting plant viruses and germs

A technology of plant pathogens and derivatives, applied in the direction of chemicals for biological control, botany equipment and methods, applications, etc., can solve the problem that the biological activity of derivatives has not been systematically studied, and the resistance to plant viruses and bacteria has not been systematically studied. Research and reporting issues, to achieve good anti-plant virus and bacteria activity effect

Active Publication Date: 2019-11-22
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] So far, although Kealiinine alkaloids have relatively mature synthetic routes and have been found to have certain anticancer and artemia-killing activities, their other biological activities, especially the activities against plant viruses and pathogens, are still unknown. Has not been systematically studied and reported, in addition, the biological activity of their derivatives has not been systematically studied

Method used

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  • Kealiinine derivative, preparation thereof and application of the derivative in resisting plant viruses and germs
  • Kealiinine derivative, preparation thereof and application of the derivative in resisting plant viruses and germs
  • Kealiinine derivative, preparation thereof and application of the derivative in resisting plant viruses and germs

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the synthesis of Kealiinine derivative II-1

[0044] Add EDCI (0.19g, 1.00mmol), HOBt (22mg, 0.16mmol), cyclopentyl formic acid (95mg, 0.83mmol) and DIPEA (0.32g, 2.49mmol) in a 100mL round bottom flask, and distill with 30mL The dichloromethane was dissolved, stirred at room temperature for 30 min, added Kealiinine B (0.30 g, 0.83 mmol), protected by argon, stirred at room temperature for 10 h, and monitored by TLC. Add 30mL of water to dilute the reaction solution, separate the layers, extract the aqueous phase with dichloromethane (30mL×3), combine the organic layers, wash with saturated brine, dry over anhydrous sodium sulfate, filter with suction, precipitate under reduced pressure, column chromatography (V (Petroleum ether): V (ethyl acetate) = 6: 1 → V (petroleum ether): V (ethyl acetate) = 4: 1 → V (petroleum ether): V (ethyl acetate) = 3: 1) , light yellow solid, yield 62%, melting point 196-197°C. 1 H NMR (400MHz, CDCl 3 )δ11.71(s, 1H), 7.42(d...

Embodiment 2

[0045] Embodiment 2: the synthesis of Kealiinine class derivative II-2

[0046] In a 100mL round bottom flask, add Kealiinine B (0.20g, 0.55mmol), DMAP (0.013g, 0.11mmol), triethylamine (0.067g, 0.66mmol), dissolve with 20mL of dichloromethane, argon protection, A solution of methanesulfonyl chloride (0.13 g, 1.13 mmol) in dichloromethane (2 mL) was slowly added dropwise thereto. After the addition was complete, the mixture was stirred at room temperature for 1 h and monitored by TLC. Add 20 mL of water to quench the reaction, separate the layers, extract the aqueous phase with dichloromethane (60 mL×3), combine the organic layers, wash with saturated brine, dry over anhydrous sodium sulfate, filter with suction, precipitate under reduced pressure, and perform column chromatography on the crude product (V (dichloromethane): V (methanol) = 50:1), 0.21 g of a light yellow solid was obtained with a yield of 86% and a melting point of 204-205°C. 1 H NMR (400MHz, CDCl 3 )δ9.76(s,...

Embodiment 3

[0047] Embodiment 3: the synthesis of Kealiinine class derivative II-3 and II-4

[0048] II-3: Kealiinine B (0.52g, 1.43mmol), benzaldehyde (0.23g, 2.17mmol), and toluene (30mL) were added to a 100mL round bottom flask, heated to 110°C, and reacted overnight. Precipitate under reduced pressure, remove toluene, add ethanol (30 mL), add sodium borohydride (0.20 g, 5.26 mmol) in batches under stirring at room temperature, react for 3 h, and monitor by TLC. Add a small amount of water to quench the reaction, remove most of the solvent under reduced pressure, add 50 mL of water, extract with dichloromethane (80 mL×3), combine the organic layers, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure Precipitation and column chromatography of the crude product (V (dichloromethane): V (methanol) = 50: 1) gave 0.49 g of a yellow solid with a yield of 76% and a melting point of 112-114°C. 1 H NMR (400MHz, CDCl 3 )δ7.57(d, J=8.4Hz, 2H), 7.30-...

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Abstract

The invention relates to a Kealiinine derivative II, a preparation method thereof and an application of the derivative II in resisting plant viruses and germs. The Kealiinine derivative II shows especially excellent plant virus resisting activity, can well inhibit tobacco mosaic viruses (TMV), and also shows certain plant pathogenic germ resisting activity.

Description

technical field [0001] The invention relates to Kealiinine derivatives and their preparation and application in resisting plant viruses and germs, belonging to the technical field of agricultural protection. Background technique [0002] The ocean is the largest treasure house of resources on the earth. Its unique marine environment (high salinity, high pressure, anoxic, low (constant) temperature, low (no) light) produces marine natural products with diverse biological activities and rich structures. So far, more than 25,000 natural products of marine biological origin have been discovered, and this number is still increasing by an average of 1,000 species per year (Nat.Prod.Rep.2014, 31(2):160-258.; Nat. Prod. Rep. 2017, 34(3): 235-294.). In the field of medicine, many marine natural products exhibit excellent medicinal activities such as antitumor, antibacterial, antiviral, and anticardiovascular diseases (Journal of Chengde Medical College, 2017, 34(4): 332-336.); In t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C07D403/12C07D401/12A01N43/52A01N47/36A01N47/38A01N47/18A01P1/00A01P3/00
CPCC07D235/02C07D403/12C07D401/12A01N43/52A01N47/36A01N47/38A01N47/18
Inventor 汪清民李刚王兹稳刘玉秀
Owner NANKAI UNIV
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