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Phenanthroindolizidine alkaloid quaternary ammonium salt derivative and preparation and plant virus resisting application thereof

A technology of phenanthroindolizidine and anti-plant virus agent, which is applied in the fields of phenanthroindolizidine alkaloid quaternary ammonium salt derivatives and their preparation and anti-plant virus applications, and can solve problems such as lack of reports, Achieve the effect of good in vivo activity, high in vitro anti-TMV activity, and excellent anti-plant virus activity

Active Publication Date: 2015-12-09
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

In the separation and identification of sylphenine, the literature has reported the methyl iodide quaternary ammonium salt derivatives to identify its exact structure [(a) GovindachariTR, LakshmikanthamMV, K.NagarajanK, PaiBR.Chemical ExaminationofTylophoraAsthmatica-IITrtrahedron, 1958, 4 by degradation reaction ,311-324;(b)GellertE,GovindachariTR,LakshmikanthamMV,RagadIS,RudzatsR,ViswanathN.TheAlkaloidsofTylophoracrebriflora:StructureandSynthesisofTylocrebrine,aNewPhenanthroindolixidineAlkuloid.TheAlkaloidsofTylophoracrebriflora,1962,1008-1014;(c)MulchandaniNB,VenkatachalamSR.AlkaloidsofPergulariapallida.Phytochemistry,1976,15(10 ), 1561-1563. (d) Lou Hongxiang, Li Xian, Chu Xiaojun, Jiang Zhiming, Zhao Yanwei. Separation of alkaloids and preparation of derivatives from the root of Baiqian in North China. Journal of Shandong Medical University, 1995, 33(2), 158-162.], in addition to the influence of the 10-position N substituent on the activity of phenanthroindolizidine alkaloids has never been studied, and the method of derivatizing the 10-position N is also lacking in reports

Method used

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  • Phenanthroindolizidine alkaloid quaternary ammonium salt derivative and preparation and plant virus resisting application thereof
  • Phenanthroindolizidine alkaloid quaternary ammonium salt derivative and preparation and plant virus resisting application thereof
  • Phenanthroindolizidine alkaloid quaternary ammonium salt derivative and preparation and plant virus resisting application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: Synthesis of phenanthrene and indolizidine alkaloid quaternization product

[0027]

[0028] Dissolve R-serphine or S-serphine (590 mg, 1.5 mmol) in CHCl 3 , then add iodomethane or bromide (3-propene bromide, 3-bromopropyne, 1-bromo-2-butyne, bromoacetonitrile, bromoacetamide, 2-bromo-N-methylacetamide, 2 -Bromo-N,N-dimethylacetamide, benzyl bromide, p-trifluoromethylbenzyl bromide, p-trifluoromethylbenzyl bromide, 2-bromoacetophenone) (3 mmol). The reaction was heated to reflux for 24-48h, and the reaction was desolvated under reduced pressure to obtain a crude product, which was then separated by normal pressure column chromatography (CH 2 Cl 2 :MeOH=20:1) to obtain the target product.

[0029] Compound I-S-1a

[0030] Pale yellow solid, Mp: 216-217°C. Yield: 20%. 1 HNMR (400MHz, DMSO-d 6)δ8.12(s, 1H), 8.10(s, 1H), 7.47(s, 1H), 7.39(s, 1H), 5.20(d, J=16.0Hz, 1H), 4.97(d, J=16.0 Hz, 1H), 4.52-4.39(m, 2H), 4.30(br, 1H), 4.07(s, 6H), 4.00(s, 3H),...

Embodiment 2

[0093] Example 2: Research on the physicochemical properties of phenanthrene and indolizidine alkaloid quaternary ammonium salt derivatives

[0094] Above-mentioned preferred phenanthrene and indolizidine alkaloid quaternary ammonium derivatives I-S-1a, I-S-1b, I-R-1a, I-R-1b, I-R-2a, I-S-7b, I-S-8a, I-S-8b, I-R- 8a, I-S-10a, I-S-10b, I-S-11a, I-S-11b, I-S-12 compared with their respective control samples (R) / (S)-siraphyrine, characterized by preferred compounds compared to known compounds Compared with it, it has outstanding advantages, specifically: (1) the chemical stability is significantly enhanced, and the deterioration speed is obviously slower than them when placed at room temperature under the same conditions or exposed to sunlight for the same time; (2) the water solubility is significantly enhanced, (R) / ( S)-sermenine is insoluble in water, and the water solubility of the above quaternary ammonium salt derivatives is greater than 5mg / mL; the above two points have a ...

Embodiment 3

[0095] Embodiment 3: the assay of anti-tobacco mosaic virus activity, assay procedure is as follows:

[0096] 1. Virus purification and concentration determination:

[0097] Virus purification and concentration determination were carried out in accordance with the SOP specification for tobacco mosaic virus compiled by the Bioassay Laboratory of the Institute of Elements, Nankai University. After the crude virus extract was centrifuged twice with polyethylene glycol, the concentration was measured and refrigerated at 4°C for later use.

[0098] 2. Compound solution preparation:

[0099] After weighing, the original drug was dissolved in DMF to prepare 1×10 5 μg / mL mother solution, and then diluted with 1‰ Tween 80 aqueous solution to the required concentration; Ningnanmycin preparation was directly diluted with water.

[0100] 3. In vitro effect:

[0101] Rub inoculation of leaves of Shanxi tobacco at the right age, rinse with running water, the virus concentration is 10 μg...

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Abstract

The invention relates to a phenanthroindolizidine alkaloid quaternary ammonium salt derivative and preparation and plant virus resisting application thereof. See the specification for the meaning of groups in the formula. The phenanthroindolizidine alkaloid quaternary ammonium salt derivative has good light stability, heat stability and water solubility, shows excellent plant virus resisting activity and can well restrain tobacco mosaic viruses (TMV).

Description

technical field [0001] The invention relates to phenanthrene and indolizidine alkaloid quaternary ammonium salt derivatives, a preparation method thereof and application of anti-plant virus. Background technique [0002] In 1935, the first phenanthrene and indolizidine alkaloid, tylophorine, was isolated and identified [RatnagiriswaranAN, VenkatachalamK. 441.], due to its unique chemical structure and remarkable biological activity, it has attracted extensive attention from chemists at home and abroad. Phenanthrene and indolizidine alkaloids mainly exist in four families of plants: Asclepiadaceae, Moraceae, Acanthaceae and Lauraceae. Among them, the most important ones are the plants of the Romoaceae. In this family, five genera of plants have been found to contain phenanthroindolizidine alkaloids, namely: Tylophora, Cyanchum, The genera Pergularia, Vinceto-xicum and Antitoxicum. Phenanthrene and indolizidine alkaloids have been found to have a wide range of biological ac...

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 汪清民韩贵芳王兹稳刘玉秀
Owner 河北祥德康宏生物科技有限公司
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