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9th-substituted tylophorine derivatives, preparation thereof, and application thereof on inhibiting activity of tobacco mosaic virus

A tobacco mosaic disease, anti-tobacco mosaic technology, applied in the field of 9-substituted sylphenine derivatives and their preparation and application in anti-tobacco mosaic virus activity, can solve the impact of biological activity No literature Reporting, biological activity and other issues, to achieve excellent anti-plant virus activity effect

Active Publication Date: 2019-03-05
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there has been no literature report on the effect of the 9-position substituent on the phenanthrene and indolizidine alkaloids on its biological activity.
The 9-position of phenanthroindolizidine alkaloids has special properties, and the C-H bond is relatively active, so the introduction of substituents at its 9-position may have a greater impact on its biological activity

Method used

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  • 9th-substituted tylophorine derivatives, preparation thereof, and application thereof on inhibiting activity of tobacco mosaic virus
  • 9th-substituted tylophorine derivatives, preparation thereof, and application thereof on inhibiting activity of tobacco mosaic virus
  • 9th-substituted tylophorine derivatives, preparation thereof, and application thereof on inhibiting activity of tobacco mosaic virus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1 Synthesis of 9-methylsilomenine (compound 1) (method 1)

[0023]

[0024] Add 0.76g (1.99mmol) of intermediate 1 to a 100mL reaction flask, 30mL of anhydrous dichloromethane, 0.3g (3.82mmol) of acetyl chloride, 0.4g (3.95mmol) of triethylamine, 4-(N,N-di Methylamino)pyridine 0.05g (0.41mmol), stirred at room temperature for 6h, the reaction solution was washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, and subjected to normal pressure column chromatography (dichloromethane:methanol=40:1 elution) Obtain white solid 0.42g, productive rate: 49%; The obtained intermediate 2 0.1g (0.24mmol) is joined in the reaction bottle of 100mL, then adds anhydrous toluene 30mL, adds phosphorus oxychloride 1mL (10.92 mmol), heated to reflux for 1 h, removed the solvent by rotary evaporation, added 30 mL of anhydrous methanol, added 0.1 g (2.64 mmol) of sodium borohydride in an ice-water bath, stirred at room temperature for 1 h, a large amo...

Embodiment 2

[0026] The 9-substituted sylphenine derivative (compound 2-9) is completed with reference to the operation steps of Example 1

[0027] Compound 2, white solid, yield 95%; melting point: 164-165°C; 1 H NMR (400MHz, CDCl 3 )δ7.82(s, 1H), 7.81(s, 1H), 7.34(s, 2H), 4.33-4.25(m, 1H), 4.11(s, 6H), 4.06(s, 3H), 4.05(s , 3H), 3.57(t, J=7.2Hz, 1H), 3.25(d, J=14.8Hz, 1H), 2.89-2.76(m, 1H), 2.61-2.51(m, 1H), 2.46(dd, J=16.8, 8.4Hz, 1H), 2.16-1.97(m, 3H), 1.97-1.82(m, 2H), 1.79-1.65(m, 2H), 1.49-1.35(m, 1H), 1.16-0.95( m, 4H), 0.71(t, J=6.8Hz, 3H); 13 C NMR (100MHz, CDCl 3 )δ148.7, 148.5, 148.0, 147.9, 130.7, 128.9, 125.8, 124.4, 124.0, 123.3, 105.3, 104.2, 103.5, 103.2, 62.9, 59.0, 56.1, 56.0, 55.9, 53.9, 30.3, 93.3, 34.3 , 24.6, 22.5, 22.0, 14.1; HRMS (ESI) calcd for C 29 h 38 NO 4 + (M+H) + 464.2795, found 464.2804.

[0028] Compound 3, pale yellow solid, yield 18%; melting point: 210-211°C; 1 H NMR (400MHz, CDCl 3 )δ7.81(s, 1H), 7.79(s, 1H), 7.53(s, 1H), 7.35(s, 1H), 4.44...

Embodiment 3

[0035] Example 3 Synthesis of 9-ethoxymethyl sylphenine (compound 10) (method 2)

[0036]

[0037]Add 0.2g (0.45mmol) of compound 4, 20mL of absolute ethanol, 0.05g (0.89mmol) of potassium hydroxide to a 50mL reaction bottle, heat to reflux for 8h, spin dry, add appropriate amount of dichloromethane and water to dissolve, separate liquid, organic phase Washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, and precipitated under reduced pressure to obtain 0.12 g of a white solid with a yield of 61% and a melting point of 155-156°C; 1 H NMR (400MHz, CDCl 3 )δ7.81(s, 1H), 7.80(s, 1H), 7.50(s, 1H), 7.32(s, 1H), 4.35-4.29(m, 1H), 4.11(s, 6H), 4.05(s , 6H), 3.97(d, J=9.6Hz, 1H), 3.76(t, J=8.4Hz, 1H), 3.60-3.47(m, 3H), 3.26(d, J=15.2Hz, 1H), 2.94 -2.84(m, 1H), 2.61-2.50(m, 2H), 2.16-1.98(m, 2H), 1.97-1.83(m, 1H), 1.81-1.67(m, 1H), 1.24(t, J= 6.8Hz, 4H); 13 C NMR (100MHz, CDCl 3 )δ 148.82, 148.77, 148.23, 148.18, 129.0, 128.1, 125.8, 124.4, 124.0...

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Abstract

The invention relates to 9th-substituted tylophorine derivatives, preparation thereof, and an application thereof on inhibiting plant viruses. The definition of R of the formula is represented in thedescription. The invention provides a novel structure that can inhibit tobacco mosaic virus, the industrialization is easy, and the synthesis is simple. The 9th-substituted tylophorine derivatives have excellent activity on inhibiting the activity of plant viruses and can well inhibit tobacco mosaic virus (TMV).

Description

technical field [0001] The invention relates to a 9-substituted sylphenine derivative and its preparation and application in resisting plant tobacco mosaic virus disease. Background technique [0002] In 1935, the first phenanthrene and indolizidine alkaloid, tylophorine, was isolated and identified (Indian J.Med.Res., 1935, 22, 433-441), due to its unique The chemical structure and remarkable biological activity have attracted extensive attention of chemists at home and abroad. For the first time, our research group discovered that this type of alkaloid has very good inhibitory activity against the extremely harmful tobacco mosaic virus (TMV), and based on this, extensive structural modification and transformation have been carried out to optimize the efficient plant virus disease Prevention and control agent NK-007. Although phenanthrene and indolizidine alkaloids have very good biological activity, they also have the disadvantages of high central nervous system toxicity...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A01N43/90A01P1/00
CPCA01N43/90C07D471/04
Inventor 汪清民闫长存刘玉秀宋红健王兹稳
Owner NANKAI UNIV
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