9-substituted seraphine derivatives and their preparation and application in anti-tobacco mosaic virus activity

A technology of tobacco mosaic virus and seraphine, which is applied in the field of 9-substituted seraphine derivatives and their preparation and application in anti-tobacco mosaic virus activity, and can solve the problems of biological activity and biological activity. The impact of no literature reports and other issues

Active Publication Date: 2021-07-06
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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  • 9-substituted seraphine derivatives and their preparation and application in anti-tobacco mosaic virus activity
  • 9-substituted seraphine derivatives and their preparation and application in anti-tobacco mosaic virus activity
  • 9-substituted seraphine derivatives and their preparation and application in anti-tobacco mosaic virus activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0023]

[0024] In a 100 mL reaction flask, 0.76 g (1.99 mmol) of intermediate 1, 30 mL of anhydrous dichloromethane, 0.3 g (3.82 mmol) of acetyl chloride, 0.4 g (3.95 mmol) of triethylamine, 4-(N,N-dichloromethane) were added. Methylamino)pyridine 0.05g (0.41mmol), the reaction was 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 atmospheric pressure column chromatography (elution with dichloromethane:methanol=40:1) 0.42 g of white solid was obtained, yield: 49%; 0.1 g (0.24 mmol) of the obtained intermediate 2 was added to a 100 mL reaction flask, then 30 mL of anhydrous toluene was added, and 1 mL of phosphorus oxychloride (10.92 mL) was added under stirring at room temperature. mmol), heated under reflux for 1 h, removed the solvent by rotary evaporation, added 30 mL of anhydrous meth...

Embodiment 2

[0026] The 9-substituted salmenine derivatives (compounds 2-9) are 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, 35.6, 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), 4.4...

Embodiment 3

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

[0036]

[0037]Add 0.2 g (0.45 mmol) of compound 4, 20 mL of absolute ethanol, 0.05 g (0.89 mmol) of potassium hydroxide to a 50 mL reaction flask, heat under reflux for 8 h, spin dry, add an appropriate amount of dichloromethane and water to dissolve, separate liquids, and the organic phase Washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, and desolvated under reduced pressure to obtain 0.12 g of white solid, yield 61%, melting point 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 )δ148.82, 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 a 9-substituted sylphenine derivative and its preparation and application in anti-plant virus. The meaning of R in the general formula can be found in the description. The invention provides a novel anti-tobacco mosaic virus structure, which is advantageous for industrialization, simple in synthesis and the like. The 9-substituted seraphine derivatives exhibit excellent anti-plant virus activity, and can well inhibit tobacco mosaic virus (TMV).

Description

technical field [0001] The present invention relates to 9-substituted walmenine derivatives and their preparation and application in resisting plant tobacco mosaic virus disease. Background technique [0002] In 1935, the first phenanthroindolizidine alkaloid, tylophorine, was isolated and identified (Indian J.Med.Res., 1935, 22, 433-441), due to its unique Its chemical structure and remarkable biological activity have attracted extensive attention from chemists at home and abroad. For the first time, our research group found that this kind of alkaloid has very good inhibitory activity against the highly harmful tobacco mosaic virus (TMV). Control agent NK-007. Although phenanthroindolizidine alkaloids have very good biological activities, they also have the disadvantages of high toxicity to the central nervous system, poor water solubility, and instability to light and heat, which affect their practical application. Therefore, further structural derivation of this class ...

Claims

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Application Information

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Patent Type & Authority Patents(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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