Topsentin derivatives and their preparation and application in anti-plant viruses and bacteria

A technology of derivatives and peanuts, applied in the direction of chemicals for biological control, botany equipment and methods, applications, etc., can solve the problems of low total yield, low natural content of alkaloids, and insufficient research on biological activity. Reaching the effect of good anti-plant virus and pathogenic bacteria 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

3-Acetylindole (11) reacts with copper bromide to obtain 3-bromoacetylindole (12), and then undergoes nucleophilic substitution with 1,1-dimethylhydrazine to obtain the key intermediate quaternary ammonium salt (13) , rearrangement of the quaternary ammonium salt (13) under heating conditions and then coupling to obtain the alkaloid Topsentin A (Deoxytopsentin, 1), the total yield of this route is low, and the rearrangement reaction conditions are harsh (structural formula 2) (Bull.SOC. Chim. Belg. 1987, 96, 809-812)
[0050] Due to the low natural content of Topsentin 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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  • Topsentin derivatives and their preparation and application in anti-plant viruses and bacteria
  • Topsentin derivatives and their preparation and application in anti-plant viruses and bacteria
  • Topsentin derivatives and their preparation and application in anti-plant viruses and bacteria

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Embodiment 1: Synthesis of Topsentin derivatives I-1 and I-7

[0076]

[0077] 61: Add (20mmol) indole and 80mL anhydrous ether into a 250mL round bottom flask, add 2.56mL (26mmol) of oxalyl chloride in ether solution dropwise at 0°C, react at 0°C for about 1.5h, monitor by TLC, the reaction is complete, Compound 60 was directly added 15 mL of absolute ethanol dropwise to the reaction solution without treatment, stirred at room temperature for 30 min, and monitored by TLC. After the reaction was completed, bright yellow powder 61 was obtained by suction filtration. The two-step yield was 86%, and the melting point was decomposed at 174°C. 1 H NMR (400MHz, DMSO-d 6 )δ12.48(s, 1H), 8.47(d, J=3.2Hz, 1H), 8.09(d, J=8.5Hz, 1H), 7.75(d, J=1.5Hz, 1H), 7.43(dd, J=8.5, 1.7Hz, 1H), 4.36(q, J=7.1Hz, 2H), 1.34(t, J=7.1Hz, 3H).

[0078] 62: In a 100mL round bottom flask, add compound 61 (5mmol), 40mL dichloromethane, add Et under stirring at 0°C 3 NO.9mL (1.4mmol) and 0.05g DM...

Embodiment 2

[0085] Embodiment 2: Synthesis of Topsentin derivatives I-2 and I-3

[0086]

[0087] I-2: Dissolve Topsentin A (0.16g, 0.5mmol) in 150mL dichloromethane, add Et 3 N (0.5mL, 3mmol), stirred at room temperature for about 10min, added Boc 2 O (0.44g, 2mmol), stirred at room temperature, monitored by TLC, after the reaction was complete, added water, extracted with dichloromethane, washed with saturated NaCl, anhydrous NaCl 2 SO 4 After drying and precipitating, column chromatography (PE:EA=15:1) separated to obtain 0.26 g of light yellow solid, yield 83%, melting point: 161-162°C. 1 H NMR (400MHz, CDCl 3 )δ8.59(s, 1H), 8.48-8.46(m, 1H), 8.26(d, J=7.7Hz, 1H), 8.19(d, J=7.2Hz, 1H), 8.05(s, 1H), 7.99(d, J=7.5Hz, 1H), 7.84(s, 1H), 7.45-7.42(m, 2H), 1.68(s, 18H), 1.53(s, 9H). 13 C NMR (100MHz, CDCl 3 )δ 179.7, 149.6, 149.0, 146.9, 145.4, 136.8, 135.9, 135.7, 135.1, 128.0, 127.7, 125.8, 124.7, 124.7, 123.6, 123.1, 122.6, 120.3, 119.0, 13.0, 115.8, 115.5 , 85.53, 84.0, 28.2, ...

Embodiment 3

[0089] Embodiment 3: Synthesis of Topsentin derivatives I-4, I-5 and I-6

[0090]

[0091] I-4: Dissolve Topsentin A (0.21g, 0.65mmol) in a mixed solution of 20mL dichloromethane and 20mL methanol, add camphorsulfonic acid (0.15g, 0.65mmol), heat to reflux for 2h, after precipitation, dichloromethane Methane was recrystallized, and 0.33 g of yellow crystals was obtained by suction filtration, yield 94.3%, melting point: 267-270°C. 1 H NMR (400MHz, DMSO-d 6 )δ12.65(s, 1H), 11.77(s, 1H), 8.76(s, 1H), 8.32(d, J=5.4Hz, 1H), 8.17(s, 2H), 8.03(d, J=7.5 Hz, 1H), 7.64(d, J=5.7Hz, 1H), 7.55(d, J=7.7Hz, 1H), 7.40-7.30(m, 2H), 7.29-7.10(m, 2H), 2.98(d , J=14.7Hz, 1H), 2.68(t, J=11.6Hz, 1H), 2.48(d, J=15.0Hz, 1H), 2.24(d, J=18.0Hz, 1H), 1.93(s, 1H ), 1.89-1.83(m, 1H), 1.80(d, J=18.1Hz, 1H), 1.42-1.20(m, 1H), 1.04(s, 3H), 0.74(s, 3H). 13 C NMR (100MHz, DMSO-d 6 )δ 216.6, 172.7, 141.8, 139.0, 137.3, 136.9, 126.4, 126.0, 124.7, 124.4, 123.3, 122.7, 121.8, 120.8, 119.8, 117.0, 114.0, ...

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Abstract

The invention relates to Topsentin derivatives I as well as preparation and application thereof in resistance to plant viruses and germs. The Topsentin derivatives I show especially excellent anti-plant virus activity, can well inhibit tobacco mosaic viruses (TMV), and also show good anti-plant germ activity, and details of referred content of substituent groups in a general formula see the specification. (The general formula is described in the specification).

Description

technical field [0001] The invention relates to Topsentin derivatives, a preparation method thereof and an application in resisting plant viruses and germs, and belongs to the technical field of agricultural protection. Background technique [0002] The ocean is the birthplace of life. Due to the special conditions of high salinity, high pressure, anoxic, and lack of light in the ocean environment, marine organisms produce many substances with special chemical structures and unique biological activities and functions during their life. It is a treasure house of marine resources for mankind. At present, more than 7,000 kinds of marine natural products have been isolated from marine organisms such as sponges, sea hares, sea squirts, seaweeds, sharks, and corals, 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 c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14A01N43/50A01P1/00A01P3/00
CPCA01N43/50C07D403/14
Inventor 汪清民冀晓霏王兹稳刘玉秀
Owner NANKAI UNIV
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