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Phenanthroindolizidine (or phenanthroquinolizidine) alkaloid derivatives, preparation methods and anti-plant virus activities thereof

A technology of phenanthroindolizidine and alkaloid derivatives, which is applied in the field of preparation and application of anti-plant virus activity, can solve problems such as less research, and achieve the effects of good anti-plant virus activity and excellent anti-plant virus activity

Active Publication Date: 2015-07-08
河北祥德康宏生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many studies on 13a-hydrophenanthrene and indolizidine alkaloids and 14a-hydrophenanthrene and quinolizidine alkaloids, 13a non-hydrogen substituted phenanthrene and There are very few studies on the derivatives of phenanthroquinolizidine alkaloids

Method used

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  • Phenanthroindolizidine (or phenanthroquinolizidine) alkaloid derivatives, preparation methods and anti-plant virus activities thereof
  • Phenanthroindolizidine (or phenanthroquinolizidine) alkaloid derivatives, preparation methods and anti-plant virus activities thereof
  • Phenanthroindolizidine (or phenanthroquinolizidine) alkaloid derivatives, preparation methods and anti-plant virus activities thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: 13a substituted phenanthroindolizidine and 14a substituted quinolizidine alkaloid derivatives I-1~I-3, I-15~I-17 and I-31~I-32 Synthesis

[0032] Synthesis of 13a-substituted phenanthrene indolizidine alkaloid derivatives I-1, I-2 and I-3:

[0033]

[0034] Synthesis of 1-tert-butyl formate-2-methyl formate-2-(2,3,7-trimethoxyphenanthrenemethyl)pyrrolidine: Add phenanthrene methanol (1.79 g, 6 mmol) in a 250 mL round bottom flask and dichloromethane, and then dropwise added phosphorus tribromide (3.25g, 12mmol) with a constant pressure dropping funnel. After the reaction was completed, water was added to the reaction system to quench the reaction. The liquid was separated, and the organic phase was washed with ice water, and the organic phase obtained from the liquid separation was evaporated by rotary evaporation to obtain the phenanthrene methyl bromide. The phenanthrene methyl bromide was carried on to the next step without further purification. In ...

Embodiment 2

[0043] Example 2: 13a-substituted phenanthroindolizidine and 14a-substituted quinolizidine alkaloid derivatives I-4, I-11~I-14, I-18, I-22~I-27 and the synthesis of I-33

[0044] Synthesis of Compounds I-4, I-11, I-12 and I-14:

[0045]

[0046] Synthesis of I-11: Add ethylene glycol (40mL), raw material ester I-1 (0.48g, 1.1mmol), hydrazine hydrate (80%, 2mL) successively in a 100mL reaction flask, heat to reflux for 2 hours, stop To react, dichloromethane (80 mL) was added to dilute the reaction, washed with water (20 mL*3), washed with saturated brine, dried over anhydrous sodium sulfate, and precipitated to obtain I-1 (0.44 g, 94%): melting point: 210 ° C decomposition; 1 H NMR (400MHz, CDCl 3 )δ8.68(s, 1H), 7.92-7.76(m, 3H), 7.42(s, 1H), 7.18(d, J=7.8Hz, 1H), 4.21(d, J=15.8Hz, 1H), 4.16(d, J=15.8Hz, 1H), 4.08(s, 3H), 4.07(s, 3H), 3.98(s, 3H), 3.82(s, 1H), 3.73(s, 1H), 3.40(d , J=15.6Hz, 1H), 3.22(s, 1H), 3.17(d, J=15.6Hz, 1H), 2.57(dd, J=16.4, 8.4Hz, 1H), 2.30-2.23...

Embodiment 3

[0054] Example 3: 13a substituted phenanthroindolizidine and 14a substituted quinolizidine alkaloid derivatives I-5~I-9, I-19~I-22, I-28~I-30 Synthesis with I-34~I-39

[0055] Synthesis of Compounds I-19, I-22 and I-28:

[0056]

[0057]Synthesis of I-22: Add dichloromethane (40mL), raw material alcohol I-16 (0.40g, 0.95mmol), DMAP (0.14g, 1.1mmol) in a 100mL reaction flask, slowly add acetyl chloride (0.08 g, 1.0 mmol) in dichloromethane (10 mL), the dropwise addition was completed, and the stirring reaction was continued for 2 hours. Precipitate under reduced pressure, add water (30mL), add saturated sodium hydroxide solution dropwise, adjust pH to 14, extract with dichloromethane (30mL*3), combine organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, remove A brown-yellow solid was dissolved and separated by column chromatography to obtain a yellow solid (0.35g, 80%): melting point 167-170°C; 1 H NMR (400MHz, CDCl 3 )δ7.85(s, 1H), 7.85(s, 1H),...

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Abstract

The invention relates to 13a substituted phenanthroindolizidine alkaloid derivatives and 14a substituted phenanthroquinolizidine alkaloid derivatives, preparation methods and anti-plant virus activities thereof, wherein various groups in a formula are defined in an instruction. The 13a substituted phenanthroindolizidine alkaloid derivatives and the 14a substituted phenanthroquinolizidine alkaloid derivatives have good light stability and good thermal stability, show excellent anti-plant virus activities, and can be provided for well inhibiting tobacco mosaic virus (TMV).

Description

technical field [0001] The present invention relates to 13a-substituted phenanthroindolizidine and 14a-substituted phenanthroquinolizidine alkaloid derivatives and their preparation and anti-plant virus activity application. Background technique [0002] Since the first phenanthrene and indolizidine alkaloid, silephine ((R)-tylophorine) (1a), was isolated in 1935, it has attracted countless botanists due to its unique chemical structure and remarkable biological activity. , synthetic chemists and pharmacologists. So far, nearly 100 phenanthrene and indolizidine alkaloids have been reported, and they mainly exist in Asclepiadaceae, Moraceae, Acanthaceae and Lauraceae plants. middle. Among nearly one hundred phenanthrene and indolizidine alkaloids and phenanthrene and quinolizidine alkaloids that have been isolated, 13a-hydrophenanthrene and indolizidine alkaloids (such as: (R)-tylophorine (1a) and (R)-antofine (1b)) are the most common. In 1984, two novel structures of ph...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07D455/03A01N43/90A01P1/00
CPCA01N43/90C07D455/03C07D471/04
Inventor 汪清民苏波蔡春龙邓萌王兹稳
Owner 河北祥德康宏生物科技有限公司
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