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4alpha-acyloxy-2'(2',6'),2alpha-polyhalogenated podophyllotoxin derivatives as well as preparation method and application thereof

A technology of podophyllotoxin and acyloxy, applied in the field of application in the preparation of botanical pesticides

Inactive Publication Date: 2014-02-05
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of E-ring halogenated 2α-chloropodophyllotoxin esters and their insecticidal activity have not been reported yet.

Method used

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  • 4alpha-acyloxy-2'(2',6'),2alpha-polyhalogenated podophyllotoxin derivatives as well as preparation method and application thereof
  • 4alpha-acyloxy-2'(2',6'),2alpha-polyhalogenated podophyllotoxin derivatives as well as preparation method and application thereof
  • 4alpha-acyloxy-2'(2',6'),2alpha-polyhalogenated podophyllotoxin derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] 1. Products: 4α-acyloxy-2′(2′,6′), 2α-polyhalogenated podophyllotoxin derivatives 1-31 (see the following for the physical and chemical properties of each derivative)

[0044] 2. Preparation method:

[0045] The following is the synthetic route of 2'(2',6')-halopodophyllotoxin:

[0046] Dissolve podophyllotoxin in anhydrous N,N'-dimethylformamide, and then dissolve N-chlorosuccinimide or N-bromosuccinimide in anhydrous N,N' -Dimethylformamide, slowly dripped into the reaction solution at 0°C, naturally warmed to room temperature, followed by TLC detection. After the reaction was complete, it was poured into water, extracted with ethyl acetate, and the combined organic phases were washed with sodium carbonate and saturated sodium chloride, dried over anhydrous sodium sulfate, concentrated, separated and purified by column chromatography to obtain 2'(2 ',6')-halogenated podophyllotoxins in pure form.

[0047]

[0048] The physical and chemical properties of 2'-chlor...

Embodiment 2

[0235] Embodiment 2: bioassay experiment

[0236] 1. Insects to be tested: armyworm larvae in the early 3rd instar, provided by the insect breeding room of the Pollution-free Pesticide Research Center of Northwest A&F University.

[0237] 2. Samples and reagents:

[0238] The samples are: toosendanin, podophyllotoxin, 2′-chloropodophyllotoxin, 2′,6′-dichloropodophyllotoxin, 2′-bromopodophyllotoxin, 2′,2α-dichloropodophyllotoxin, 2',6',2α-trichloropodophyllotoxin, 2'-bromo-2α-chloropodophyllotoxin and compound 1-31. The solvent was acetone, analytically pure, from Chengdu Kelong Chemical Reagent Factory.

[0239] 3. Bioassay method:

[0240] Using the method of adding small leaf butterfly: spread a layer of filter paper on the bottom of a petri dish with a diameter of 9 cm, and add water to moisturize it. Pick 10 3rd instar prophase armyworm larvae with the same size and robustness from each dish. Weigh 5 mg toosendanin, podophyllotoxin, 2′-chloropodophyllotoxin, 2′,6′-dichl...

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Abstract

The invention discloses a series of new 4alpha-acyloxy-2'(2',6'),2alpha-polyhalogenated podophyllotoxin derivatives and a preparation method thereof. The chemical general formula of the series of 4alpha-acyloxy-2'(2',6'),2alpha-polyhalogenated podophyllotoxin derivatives is shown in the specification, wherein X is Cl, Y is H, or X and Y are Cl, or X is Br and Y is H. The preparation method comprises the following steps: performing E-cyclohalogenation, C-4 hydroxy protection, C-2alpha-chloro, and C-4 deprotection on podophyllotoxin used as a raw material so as to obtain 2'(2',6'),2alpha-polyhalogenated podophyllotoxin, and finally reacting DMAP / DCC or BF3.Et2O used as a esterification reagent C-4-OH with 11 carboxylic acids so as to obtain the 4alpha-acyloxy-2'(2',6'),2alpha-polyhalogenated podophyllotoxin derivatives, wherein the C-cycloacrylated product is produced in accompanying when the BF3.Et2O is used as the esterification reagent. The test shows that the 4alpha-acyloxy-2'(2',6'),2alpha-polyhalogenated podophyllotoxin derivatives have good insecticidal activity which is partially higher than that of the podophyllotoxin, wherein the insecticidal activities of a plurality of compounds are higher than that of commercial botanical pesticide toosendanin, and a botanical insecticide with high efficiency and low toxicity can be hopefully prepared from the 4alpha-acyloxy-2'(2',6'),2alpha-polyhalogenated podophyllotoxin derivatives.

Description

technical field [0001] The present invention relates to a series of 4α-acyloxy-2′(2′,6′), 2α-polyhalogenated podophyllotoxin derivatives with insecticidal activity and a preparation method thereof, and the series of 4α-acyloxy- Application of 2'(2',6'), 2α-polyhalogenated podophyllotoxin derivatives in the preparation of botanical insecticides. Background technique [0002] Podophyllotoxin is a kind of cyclolignan lactone with good biological activity. It was first isolated from Podophyllum scutellaria, and mainly exists in the genus Anise, Heliconia and Peach in the family Berberidaceae. It has attracted much attention because of its antitumor, antiviral, antifungal and other activities. For example: Etoposide (VP-16) and Teniposide (VM-26), derivatives of podophyllotoxin, have obvious inhibitory effects on small cell lung cancer, Cuiwan cancer, acute leukemia, and malignant lymphoma. role, and has been widely used clinically; literature [Catherine Tung-Ling Lee, Victor C...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04A01N43/90A01P7/04
CPCA01N43/90C07D493/04
Inventor 徐晖樊玲玲
Owner NORTHWEST A & F UNIV
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