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Pityriacitrin alkaloid derivative containing acylthiourea structure as well as preparation method and application of pityriacitrin alkaloid derivative

A technology of alkaloid derivatives and acylthiourea, which is applied in the fields of botanical equipment and methods, chemicals for biological control, biocides, etc., can solve the problem of high cost, low natural content of pityriacitrins alkaloids, and synthetic yields. Low problems, to achieve the effect of good anti-plant virus and fungus activity

Active Publication Date: 2021-08-20
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 acylthiourea structure as well as preparation method and application of pityriacitrin alkaloid derivative
  • Pityriacitrin alkaloid derivative containing acylthiourea structure as well as preparation method and application of pityriacitrin alkaloid derivative
  • Pityriacitrin alkaloid derivative containing acylthiourea structure as well as preparation method and application of pityriacitrin alkaloid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1

[0027] The preparation method of the pityriacitrin alkaloid derivative containing the acylthiourea structure with the chemical structural formula I is as follows:

[0028] The prepared pityriacitrin alkaloid derivatives containing an acylthiourea structure have the following chemical structure formula I:

[0029]

[0030] 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...

Embodiment 2

[0035] The preparation method of N-phenyl-2-(pyrido[3,4-b]indole-1-carbonyl)hydrazide-1-thioamide shown in chemical structural formula I-1 is as follows:

[0036] The chemical structural formula I-1 of N-phenyl-2-(pyrido[3,4-b]indole-1-carbonyl)hydrazide-1-thioamide is

[0037]

[0038] The concrete steps of its preparation method are as follows:

[0039] 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,...

Embodiment 3

[0045] The preparation method of N-(4-methylphenyl)-2-(pyrido[3,4-b]indole-1-carbonyl)hydrazide-1-thioamide shown in chemical structural formula I-2 is as follows:

[0046] The chemical structural formula I-2 of N-(4-methylphenyl)-2-(pyrido[3,4-b]indole-1-carbonyl)hydrazide-1-thioamide is

[0047]

[0048] The concrete steps of its preparation method are as follows:

[0049] The first step to the fourth step, with embodiment 1;

[0050] In the fifth step, except that 4-methylphenyl isothiocyanate is used, the others are the same as in Example 1, and ether recrystallization is purified to obtain a white solid with a yield of 78%; after determination, the relevant parameters of the white solid are: : 1 H NMR (400MHz, CDCl 3 )δ10.08(s,1H,NH),8.18(s,1H,ArH),7.84(d,J=7.22Hz,1H,ArH),7.75(s,1H,ArH),7.43–7.42(m, 1H,ArH),7.35–7.29(m,3H,ArH),7.17(t,J=7.1Hz,1H,ArH),6.99(d,J=7.1Hz,2H,ArH),2.17(s,3H, CH 3 ); 13 C NMR (100MHz, CDCl 3 )δ180.8,165.0,141.1,137.1,136.3,135.1,134.7,13...

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Abstract

The invention discloses a pityriacitrin alkaloid derivative containing an acylthiourea structure as well as a preparation method and application of the pityriacitrin alkaloid derivative, and relates to a biocide of the pityriacitrin alkaloid derivative containing beta-carboline and containing the acylthiourea structure at the first position, and the pityriacitrin alkaloid derivative containing the acylthiourea structure has a chemical structural general formula I shown in the description. According to the preparation method, the specific steps are shown as a chemical reaction equation defined in the description, and the pityriacitrin alkaloid derivative can be used as a plant virus resisting agent and a plant pathogenic fungus killing agent.

Description

technical field [0001] The present invention is a pityriacitrin alkaloid derivative containing an acylthiourea structure and its preparation method and application, and relates to a biocide of a β-carboline heterocyclic compound containing an acylthiourea structure at the 1-position, specifically pityriacitrin containing an acylthiourea structure Alkaloid derivatives and their preparation and use. 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 - pityriacitrin and 2'-MeO-6'-OH-pityriacitrin and other pityriacitrins alkaloids (Mini. Rev. Med. Chem., 2021, 21, 233-244.), as shown in structural formula 1. [0003] [0004] Since the Japanese rese...

Claims

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Application Information

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IPC IPC(8): C07D471/04A01N47/34A01P1/00A01P3/00A01P7/04
CPCC07D471/04A01N47/34Y02A50/30
Inventor 卢爱党马钰聪王铁男李红岩王兹稳陈建新
Owner HEBEI UNIV OF TECH
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