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Pityriacitrin alkaloid derivative containing acylhydrazone structure and its preparation method and use

A technology of alkaloid derivatives and acylhydrazones, which is applied in the field of pityriacitrin alkaloid derivatives containing an acylhydrazone structure and its preparation, can solve the problems of high cost, low natural content of pityriacitrins alkaloids, low synthesis yield, etc., and achieve good results Anti-Plant Virus and Pathogen Activity Effect

Active Publication Date: 2022-05-17
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Through literature research, due to the low natural content of pityriacitrins alkaloids, low synthesis yield and high cost, researchers mainly focus on the application of pityriacitrins in medicine, especially anti-tumor, and there are few reports on the control of diseases and insect pests.

Method used

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  • Pityriacitrin alkaloid derivative containing acylhydrazone structure and its preparation method and use
  • Pityriacitrin alkaloid derivative containing acylhydrazone structure and its preparation method and use
  • Pityriacitrin alkaloid derivative containing acylhydrazone structure and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation method of the pityriacitrin alkaloid derivative containing the acylhydrazone structure with the chemical structural formula I is as follows:

[0027] The prepared pityriacitrin alkaloid derivatives containing an acylhydrazone structure have the following chemical structure formula I:

[0028]

[0029] In the above chemical structural formula I, R represents methyl, propyl, isopropyl, n-butyl, n-butyl, tert-butyl, benzyl, cyclopentyl, cyclohexyl, phenyl, 2-fluorophenyl , 3-fluorophenyl, 3,4-difluorophenyl, 2,6-difluorophenyl, 2,4-difluorophenyl, 2,3-difluorophenyl, 4-fluorophenyl, 2 -Chlorophenyl, 3-chlorophenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl, 2,4-dichlorophenyl, 2,3-dichlorophenyl, 2,5 -Dichlorophenyl, 4-chlorophenyl, 5-chloro-2-fluorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 4-iodophenyl, 2-nitro Phenyl, 3-nitrophenyl, 4-nitrophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-trifluoromethylphenyl, 3-tri Fluoromethylphen...

Embodiment 2

[0034] The preparation method of N'-benzylidene-pyrido[3,4-b]indole-1-carboxylhydrazide shown in chemical structural formula I-1 is as follows:

[0035] The chemical structural formula I-1 of N'-benzylidene-pyrido[3,4-b]indole-1-formyl hydrazide is

[0036]

[0037] The concrete steps of its preparation method are as follows:

[0038] The first step, after mixing the aqueous solution of glyoxylic acid monohydrate (10.37g, mass fraction 50%) and ethyl acetate (145mL), add K 2 CO 3 An aqueous solution (20 mL, 10% by mass) was adjusted to pH 5, and tryptamine (9.60 g, 60 mmol) was slowly added under stirring to fully dissolve it, and then stirred and reacted at room temperature for 24 hours. After the reaction, filter, and wash the solid product with ethyl acetate and a small amount of ethanol, and dry to obtain 10.702g of yellow solid compound 1, with a yield of 83%. After determination, the relevant parameters of the yellow solid are: 1 H NMR (400MHz, DMSO-d 6 )δ2.81–2.8...

Embodiment 3

[0044] The preparation method of N'-(4-methylbenzylidene)-pyrido[3,4-b]indole-1-carboxylhydrazide shown in chemical structural formula I-2 is as follows:

[0045] The chemical structural formula I-2 of N'-(4-methylbenzylidene)-pyrido[3,4-b]indole-1-formyl hydrazide is

[0046]

[0047] The concrete steps of its preparation method are as follows:

[0048] The first step to the fourth step, with embodiment 1;

[0049] In the fifth step, except that 4-methylbenzaldehyde is used, the others are the same as in Example 1, and diethyl ether is recrystallized and purified to obtain a light yellow solid with a yield of 92%; after determination, the relevant parameters of the light yellow solid are: 1 H NMR (400MHz, DMSO-d 6 )δ11.24 (s,1H,CONH),11.83(s,1H,NH),8.69(s,1H,N=CH),8.44(d,J=4.3and 22.4Hz,2H,ArH),7.84( d,J=8.1Hz,1H,ArH),7.84(d,J=8.1Hz,1H,ArH),7.65(d,J=7.5Hz,2H,ArH),7.60(t,J=7.7Hz,1H ,ArH),7.30–7.28(m,2H,ArH),2.35(s,3H,CH 3 ); 13 C NMR (100MHz, DMSO-d 6 )δ161.7, 148.7,...

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Abstract

The present invention contains acylhydrazone structure pityriacitrin alkaloid derivatives and its preparation method and application, and relates to a biocide containing β-carboline and acylhydrazone structure pityriacitrin alkaloid derivatives, and acylhydrazone structure pityriacitrin alkaloids The derivative has the following chemical structure formula I, its preparation method, the specific steps are shown in the following chemical reaction equation, and its use is as an anti-plant virus agent and as a phytopathogenic fungicide.

Description

technical field [0001] The technical solution of the present invention relates to a biocide containing β-carboline and a pityriacitrin alkaloid derivative containing an acylhydrazone structure at the first position, specifically a pityriacitrin alkaloid derivative containing an acylhydrazone structure and its preparation method and application. Background technique [0002] Pityriacitrins alkaloids are a class of β-carboline alkaloids with a novel structure, in which an indole structure is linked at the C-1 position of β-carboline through a carbonyl functional group. Compounds containing such core skeletons extracted from nature include pityriacitrin, pityriacitrin B, hytiosulawesine, 7-MeO-pityriacitrin, 7,2’-(MeO) 2 Pityriacitrins alkaloids such as -pityriacitrin and 2'-MeO-6'-OH-pityriacitrin (Mini. Rev. Med. Chem., 2021, 21, 233-244.), as shown in structural formula 1. [0003] [0004] Since the Japanese research team first reported the isolation of pityriacitrins a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A01N43/90A01P3/00
CPCC07D471/04A01N43/90Y02A50/30
Inventor 卢爱党王禄王铁男李红岩王兹稳陈建新
Owner HEBEI UNIV OF TECH
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