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13-aminoxanthatin derivatives and preparation method and application thereof

A technology of Xanthomonas and derivatives, which is applied in the field of 13-aminoxanthium derivatives and their preparation, can solve problems such as no reports on activity research, and achieve the effect of strong poisoning activity

Active Publication Date: 2019-11-12
SHANXI AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of this, at present, Xanthiting and its derivatives are researched on anti-tumor, anti-inflammatory, anti-ulcer, insecticidal and bacteriostatic, but Xanthiting and its derivatives are effective in killing diamondback moth and various plant pathogenic fungi. There is no report on the activity of spore germination inhibition

Method used

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  • 13-aminoxanthatin derivatives and preparation method and application thereof
  • 13-aminoxanthatin derivatives and preparation method and application thereof
  • 13-aminoxanthatin derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The following is the synthetic route of compound 1-20:

[0021] Dissolve a certain amount of Xanthin and secondary amine in methanol, then stir and react at room temperature or in an oil bath, and track and detect with TLC. After the reaction is completed, concentrate the reaction solution under reduced pressure, and prepare silica gel thin plate chromatography to obtain the desired target product.

[0022] The numbers of compounds 1-20 correspond to the numbers (1)-(20) of R in the general chemical formula respectively.

[0023]

[0024] The physical and chemical properties of compound 1 are as follows:

[0025] 1) Pale yellow liquid;

[0026] 2) The nuclear magnetic resonance spectrum characteristic of this compound:

[0027] With deuterated chloroform as solvent, TMS as internal standard, wherein each peak belongs to: 1 H NMR (500MHz, CDCl 3 )δ: 7.07 (d, J = 16.0Hz, 1H, 2-H), 6.26 (d, J = 9.0Hz, 1H, 5-H), 6.19 (d, J = 16.0Hz, 1H, 3-H) ,4.29-4.34(m,1H,8-H),3....

Embodiment 2

[0148] Insecticidal activity test:

[0149] 1. Insects to be tested: larvae of diamondback moth (Plutella xylostella) at the end of the 2nd instar.

[0150] 2. Samples and reagents: raw material Xanthin, Xanthin derivatives 1-20 prepared in the examples, and positive control drug toosendanin (>98%); solvent is acetone (analytical pure).

[0151] 3. Bioassay method:

[0152] Using the small leaf dish addition method: spread a layer of filter paper on the bottom of a 9cm-diameter petri dish, and add water to moisturize it. Pick 20 larvae of Plutella xylostella xylostella at the end of the second instar with the same size and robustness in each dish. Weigh appropriate amounts of toosendanin, xanthin and compound 1-20 prepared in the examples and add acetone to prepare a drug solution with a concentration of 20 mg / ml. Cut the cabbage leaves into 1×1cm small leaf discs, use a micro-dropper to measure 2 μL of the drug solution to be tested and apply it evenly on the surface of the ...

Embodiment 3

[0159] Antibacterial activity test:

[0160] 1. Pathogens tested: Alternaria solani, Fusarium solani, Botrytis cinerea, Colletotrichum morbiculare, provided by the Plant Pathology Laboratory of Shanxi Agricultural University.

[0161] 2. Samples and reagents:

[0162] The samples are: raw material Xanthin, Xanthin derivatives 1-20 prepared in the examples, and positive control agents difenoconazole (98%) and hymexazol (99%); the solvent is DMSO (chromatographically pure) , the emulsifier is Tween-80 (excellent pure).

[0163] 3. Bioassay method:

[0164] Using the method of inhibiting spore germination:

[0165] (1) Preparation of spore suspension: add sterile water to the cultured plate of sporulated strains, gently rub the surface of the culture medium with an inoculation loop, and then filter out mycelia and culture medium with double-layer gauze. Add appropriate sterile water to the spore suspension and stir. Observe under a 100X microscope, preferably 30-40 spores pe...

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Abstract

The invention provides 13-aminoxanthatin derivatives. A chemical formula of the derivatives is as shown in the specification. A preparation method comprises the following steps: carrying out a Michaeladdition reaction outside the ring of xanthatin and secondary amines to prepare the derivatives. A series of new 13-aminoxanthatin derivatives are synthesized, the derivatives have relatively strongtoxic activity against plutella xylostella, and have a certain inhibition effect against spore germination of alternaria solani, fusarium solani, botrytis cinerea and colletotrichum orbiculare. Therefore the derivatives can be used to prepare efficient and low-toxic plant-derived insecticides and bacteriostatic agents.

Description

technical field [0001] The invention relates to the technical field of xanthine derivatives, in particular to 13-amino xanthine derivatives and their preparation methods and applications. Background technique [0002] Xanthatin is a sesquiterpene lactone compound in the Compositae (Compositae) Xanthium L. plant, because of its anti-tumor, anti-inflammatory, insecticidal and bacteriostatic properties. biological activity has become the focus of research. [0003] In the existing literature, Xanthiting and its derivatives have been studied in the aspects of anti-tumor, anti-cancer, anti-inflammation, anti-ulcer, inhibition of enzyme activity, insecticide and bacteriostasis: Literature [Geng Ya-di, Zhang Lei, Wang Guo-Yu, et al. Xanthatin mediates G 2 / M cell cycle arrest,autophagy and apoptosis via ROS / XIAP signaling in human colon cancer cells[J].Natural product research,2018:1-5.] found that Xanthin can inhibit and mediate the apoptosis and apoptosis of human colon cancer ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/93C07D405/06A01N43/12A01N43/40A01N43/60A01N43/36A01N43/84A01P3/00A01P7/04
CPCA01N43/12A01N43/36A01N43/40A01N43/60A01N43/84C07B2200/07C07D307/93C07D405/06
Inventor 郅晓燕李婷
Owner SHANXI AGRI UNIV
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