Indolylhydrazone derivative as well as preparation method and application thereof to prevention and control of plant viruses, sterilization and disinsection

A technology of indolehydrazone and derivatives, applied in the field of pesticides, to achieve excellent anti-plant virus activity and good anti-tobacco mosaic virus effect

Active Publication Date: 2020-02-07
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In 2017, Boominathan et al. reported that under the catalysis of a catalytic amount of TfOH, the efficient realization of aza Synthesis of [4,5-b] indoles (Org. Biomol. Chem., 2017, 15(8): 1872-1875.), but its biological activity is still under test and has not been reported

Method used

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  • Indolylhydrazone derivative as well as preparation method and application thereof to prevention and control of plant viruses, sterilization and disinsection
  • Indolylhydrazone derivative as well as preparation method and application thereof to prevention and control of plant viruses, sterilization and disinsection
  • Indolylhydrazone derivative as well as preparation method and application thereof to prevention and control of plant viruses, sterilization and disinsection

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Experimental program
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preparation example Construction

[0059] The present invention provides a kind of above-mentioned tetrahydroazepine The preparation method of [4,5-b] indolehydrazone derivatives, the method comprises: first, L-tryptophan in SOCl 2 Catalyzed esterification reaction with methanol to generate L-tryptophan methyl ester (I), L-tryptophan methyl ester under triethylamine alkaline conditions on the Ts protecting group to form II, II respectively with α-bromobenzene Ethanone undergoes nucleophilic substitution to generate III, and then undergoes dehydration condensation and ring-closing rearrangement under the catalysis of trifluoromethanesulfonic acid to generate the corresponding IV, IV undergoes hydrazine hydrolysis to generate the corresponding hydrazide V, and the intermediate V is aldehyde-condensed to obtain the general Tetrahydroazepine And [4,5-b] indolehydrazone compound;

[0060]

[0061] Among them, R 1 , R 2 , R 3 As described above, the present invention will not be repeated here.

[0062] The...

Embodiment 1

[0081] Embodiment 1: Tetrahydroazepine Synthesis of [4,5-b]indolehydrazone Derivative VI-1

[0082]

[0083] L-Tryptophan methyl ester (I)

[0084] 10.31 g (50 mmol) of L-tryptophan and 150 mL of anhydrous methanol were added to a 250 mL round bottom flask, and 10 mL of thionyl chloride was slowly added in an ice-water bath. After dropping, the solution was clarified and heated to reflux for 5 hours. After the reaction was complete as detected by TLC, the solvent was removed, washed with saturated sodium carbonate solution, extracted with ethyl acetate (50mL×3), washed with saturated brine three times, dried over anhydrous sodium sulfate, and suction filtered. Rotary evaporation gave 10.51 g of a brown solid, with a yield of 96%. Melting point: 90-91°C. 1 H NMR (400MHz, CDCl 3 )δ8.65 (s, 1H, Ar-NH), 7.60 (d, J=8.0Hz, 1H, Ar-H), 7.29 (d, J=8.0Hz, 1H, Ar-H), 7.16(t, J=7.2Hz, 1H, Ar-H), 7.10(t, J=7.2Hz, 1H, Ar-H), 6.95(d, J=2.4Hz, 1H, C=CH), 3.84(dd, J= 8.0, 4.8Hz, 1H, ...

Embodiment 2

[0169] Embodiment 2: the assay of anti-tobacco mosaic virus activity, assay procedure is as follows:

[0170] 1. Virus purification and concentration determination:

[0171] 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.

[0172] 2. Compound solution preparation:

[0173] 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.

[0174] 3. In vitro effect:

[0175] 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 tetrahydroaza [4,5-b] indolylhydrazone derivative as well as a preparation method and application thereof to prevention and control of plant virtuses, sterilization and disinsection, and the meaning of each group in a general formula is shown as a specification. The tetrahydroaza [4,5-b] indolylhydrazone derivative disclosed by the invention has excellent anti-plant-virus activity and further has broad-spectrum bactericidal activity and insecticidal activity.

Description

technical field [0001] The present invention relates to tetrahydroazepine The bi[4,5-b] indolehydrazone derivatives, their preparation methods and their applications in plant virus control, bactericidal and insecticidal aspects belong to the technical field of pesticides. Background technique [0002] Aza And[4,5-b]indole structures are important heterocyclic structural units found in a series of bioactive molecules and natural products. Such as PNU-22394 is a potent 5-HT 2c Agonists may have certain effects in the treatment of obsessive-compulsive disorder, anxiety, and obesity; dopamine receptor: the human brain secretes a dopamine receptor, and the lack of dopamine receptors in the human body will slow down the response and easily cause obesity. Natural products such as subincanadine F, ngouniensine, and ibogamine have remarkable pharmaceutical properties, showing certain anticancer, cyclin-dependent kinase (CDK) inhibitors, and glycogen synthase kinase inhibitors. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P7/04A01P7/02A01P1/00A01P3/00
CPCC07D487/04A01N43/90
Inventor 汪清民宋红健李丽丽刘玉秀王兹稳李永强
Owner NANKAI UNIV
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