Camlexin derivative as well as preparation method and application thereof

A technology of derivatives and phytoalexin, applied in the field of fine chemicals, can solve the problem of low activity and achieve the effect of expanding the scope of application

Pending Publication Date: 2022-04-22
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The purpose of the present invention is to provide a camalexin derivative and its preparation method and use in view of the problem that the camalexin derivative has various activities and good environmental compatibility, but its activity is relatively low.

Method used

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  • Camlexin derivative as well as preparation method and application thereof
  • Camlexin derivative as well as preparation method and application thereof
  • Camlexin derivative as well as preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0036] The preparation method of described phytoalexin camalexin derivative, concrete steps are as shown in following reaction formula four:

[0037]

[0038] Using 5-bromo-1H-indole-3-carbothioamide shown in chemical structural formula 3e as raw material, reacting with ethyl 3-bromopyruvate in an ethanol solvent under heating and reflux to generate 2 as shown in chemical structural formula 5 -(5-bromo-1H-indol-3-yl)thiazole-4-formic acid ethyl ester intermediate product; the intermediate product is dissolved in ethanol, and 80% hydrazine hydrate is added to undergo hydrazinolysis reaction under heating conditions to obtain as chemical Important intermediate 2-(5-bromo-1H-indol 3-yl)thiazole-4-carbohydrazide shown in structural formula 6; finally 2-(5-bromo-1H-indol 3-yl)thiazole-4 -carbohydrazide reacts with different substituted aldehyde compounds to obtain 2-(5-bromo-1H-indol-3-yl)-N'-methylenethiazole-4 as shown in the general formula I - carbohydrazide.

[0039] The ...

Embodiment 1

[0041]

[0042] The preparation method of (E)-N'-benzylidene-2-(5-bromo-1H-indol-3-yl)thiazole-4-carbohydrazide shown in chemical structural formula I-1 is:

[0043] In the first step, chlorosulfonic acid isocyanate (12 mmol) was added dropwise to a solution of 5-bromoindole (10 mmol) in DMF (10 mL) under nitrogen protection at -50°C, and after the addition was completed, the temperature was raised to room temperature to continue the reaction for 1.5 hours. After the reaction was detected by TLC, the reaction system was poured into ice water, stirred for 30 minutes, and filtered with suction to obtain a yellow solid 5-bromo-1H-indole-3-carbonitrile with a yield of 99% and a melting point of 185-186°C; 1 H NMR (400MHz, CDCl 3 )δ9.18(s, 1H), 7.93(s, 1H), 7.76(s, 1H), 7.45(d, J=8.7Hz, 1H), 7.39(d, J=8.7Hz, 1H); 13 C NMR (100MHz, DMSO-d 6 )δ 135.9, 134.0, 128.4, 126.1, 120.7, 115.6, 115.0, 114.4, 84.0, the product was determined to be 5-bromo-1H-indole-3-carbonitrile.

[004...

Embodiment 2

[0049]

[0050] (E)-2-(5-bromo-1H-indol-3-yl)-N'-(4-methoxybenzylidene)thiazole-4-carbohydrazide shown in chemical structure I-2 The preparation method is:

[0051] Except that the fifth step is 4-methoxybenzaldehyde instead of benzaldehyde, the others are the same as in Example 1, a white solid with a yield of 56% and a melting point of >300°C; 1 H NMR (400MHz, DMSO-d 6 )δ12.08(s,1H),11.71(s,1H),8.59(s,1H),8.54(s,1H),8.30(s,1H),8.29(s,1H),7.72(d,J =8.7Hz, 2H), 7.49(d, J=8.6Hz, 1H), 7.39(d, J=8.6Hz, 1H), 7.06(d, J=8.7Hz, 2H), 3.83(s, 3H); 13 C NMR (100MHz, DMSO-d 6 C 20 h 16 BrN 4 o 2 S[M+H] + 455.0172, found (ESI + ) 455.0173, the product was determined to be (E)-2-(5-bromo-1H-indol-3-yl)-N'-(4-methoxybenzylidene)thiazole-4-carbohydrazide.

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Abstract

The invention relates to a camalexin derivative as well as a preparation method and application thereof. The structural general formula of the phytoalexin camalexin derivative is as shown in I. According to the derivative, a new substituent group is introduced on the basis of alkaloid camalexin, a bromine atom is introduced to the fifth position in an indole structural unit of a core skeleton of a natural product camalexin, a hydrazide hydrazone functional group is introduced to the fourth position in a thiazole structural unit, and a series of camalexin derivatives are generated. The alkaloid phytoalexin camalexin derivative disclosed by the invention has very good plant virus resisting activity and broad-spectrum phytopathogen killing activity.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to plant-alexin camalexin derivatives and their preparation and application as a biocide in agriculture. Background technique [0002] Camalexin (3-thiazol-2'-yl-indole, as shown in structural formula 1) is a unique phytoalexin of cruciferous plants, also known as camelinin, it is a sulfur-containing indole alkaloid, Representative phytoalexins or phytoalexins produced by cruciferous plants after external stimuli can be induced by various pathogens (such as bacteria, fungi, viruses, oomycetes, etc.) [Glawischnig, E. Camalexin. Phytochem. 2007, 68(4), 401–406.]. [0003] [0004] Since Browne et al [Browne, L.M; Conn, K.L; Ayer, W.A; Tewari, J.P.Tetrahedron1991, 47 (24), 3909–3914.] first isolated the phytoalexin camalexin from the leaves of Camellia japonica in 1991, phytoalexin camalexin and Its derivatives not only protect crops in agricultural production, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04C07D417/14A01N43/78A01P1/00
CPCC07D417/04C07D417/14A01N43/78
Inventor 卢爱党李林王兹稳廖安财
Owner HEBEI UNIV OF TECH
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