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1-Methyl-5-bromophylline derivatives and their preparation methods and uses

A technology of rubarine and derivatives, which is applied in the field of 1-methyl-5-bromorubarine derivatives and preparation thereof, can solve problems such as high production cost, environmental pollution, low yield, etc., and achieves good resistance to plants. Effects of viral and bacterial activity

Active Publication Date: 2020-05-26
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The technical problem to be solved by the present invention is to provide 1-methyl-5-bromophylline derivatives and their preparation methods and uses, wherein the 1-methyl-5-bromophylline derivatives are brand-new Alkaline derivatives, the preparation method of which overcomes the defects of low yield, high production cost and environmental pollution in the preparation of catarrhine derivatives in the prior art, and discovers 1-methyl-5-bromophyllidine derivatives for the first time Possesses good activity against plant viruses and pathogens

Method used

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  • 1-Methyl-5-bromophylline derivatives and their preparation methods and uses
  • 1-Methyl-5-bromophylline derivatives and their preparation methods and uses
  • 1-Methyl-5-bromophylline derivatives and their preparation methods and uses

Examples

Experimental program
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Effect test

Embodiment 1

[0034] The preparation method of 1-methyl-5-bromophylline derivative with chemical structural formula I is as follows:

[0035] The prepared 1-methyl-5-bromophylline derivative has the following chemical structure formula I:

[0036]

[0037] In the general formula I of the above chemical structure, HX represents an inorganic acid or an organic acid, and when HX represents an inorganic acid, it is HCl, HBr, HI, H 2 SO 4 or H 3 PO 4, when HX represents an organic acid, it is dichloroacetic acid, trifluoroacetic acid, propionic acid, butyric acid, malonic acid, oxalic acid, adipic acid, camphorsulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, trans ferulae Acid, salicylic acid, malic acid, succinic acid, p-hydroxybenzoic acid, lactic acid, caffeic acid, chlorogenic acid, sulfanilic acid, 5-sulfosalicylic acid, fumaric acid, gluconic acid, itaconic acid or sorbic acid.

[0038] The specific steps of the preparation method of the 1-methyl-5-bromophylline derivat...

Embodiment 2

[0042] The preparation method of 1-methyl-5-bromophylline benzoate shown in chemical structural formula I-1 is as follows:

[0043] The chemical structural formula I-1 of 1-methyl-5-bromophylline benzoate is

[0044]

[0045] The concrete steps of its preparation method are as follows:

[0046] In the first step, add 5 mL of DMF and 5 mL of formaldehyde solution with a mass percentage concentration of 37% to a 150 mL reactor at a temperature of 0 to 5° C. and magnetic stirring at 600 rpm. % dimethylamine aqueous solution is 33.5mmol of dimethylamine, 2.855mL of glacial acetic acid was added dropwise after 1h, and reacted for 15min, and then 3.20g (15.23mmol) of raw material 1-methyl-5-bromoindole was added, and after 1.5h of reaction, Transfer to room temperature and continue the reaction for 12 hours. After the completion of the reaction was detected by TLC spotting, first add saturated saline, then add a 30% NaOH aqueous solution by mass percentage, adjust the pH of the ...

Embodiment 3

[0049] The preparation method of 1-methyl-5-bromophylline L malate shown in chemical structural formula I-2 is as follows:

[0050] The chemical structural formula I-2 of 1-methyl-5-bromophylline L malate is

[0051]

[0052] The concrete steps of its preparation method are as follows:

[0053] The first step, with embodiment 1;

[0054] In the second step, except that benzoic acid is replaced with L malic acid, the others are the same as in Example 1, and purified by column chromatography to obtain a light yellow oil with a yield of 94%; 1 H NMR (400MHz, DMSO-d 6 )δ7.94(d, J=1.7Hz, 1H, Ar-H), 7.46(s, 1H, Ar-H), 7.44(d, J=8.7Hz, 1H, Ar-H), 7.30(dd, J=1.8,8.7Hz,1H,Ar-H),4.00(s,2H,Ar-CH 2 ),3.86–3.92(m,1H,CH 2 -CH),3.79(s,3H,N-CH 3 ),3.18(s,3H,CO 2 H,OH),2.49–2.56(m,1H,CH-CH 2 ),2.46(s,6H,N-(CH 3 ) 2 ),2.31–2.38(m,1H,CH-CH 2 ); 13 C NMR (100MHz, DMSO-d 6 )δ 177.2, 172.7, 135.8, 132.8, 129.9, 124.4, 121.9, 112.6, 106.5, 66.5, 52.5, 49.1, 43.2, 42.2, 33.2, the prod...

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Abstract

The invention discloses a 1-methyl-5-Bromogramine derivative and a preparing method and application thereof, and relates to a biocidal agent containing a five-membered heterocyclic compound with one nitrogen atom as an only ring heteroatom. The 1-methyl-5-Bromogramine derivative has the following chemical structural formula, namely, the general formula I (The formula is defined in the description). The preparing method of the 1-methyl-5-Bromogramine derivative includes the following specific steps shown as the chemical reaction equation (The formula is defined in the description); the 1-methyl-5-Bromogramine derivative is used as an anti-plant-virus agent and a plant-pathogenic-fungus killing agent.

Description

technical field [0001] The technical scheme of the present invention relates to the biocide containing the five-membered ring heterocyclic compound with 1 nitrogen atom as the only ring heteroatom, specifically 1-methyl-5-bromophylline derivative and its preparation Methods and uses. Background technique [0002] Phylloline is a natural alkaloid containing an indole skeleton. Its basic structural skeleton is a tertiary amine structure and an indole structure. Its chemical structural formula is as follows: [0003] [0004] Phylloline has extremely high biological activity. Widely distributed in nature, it is an allelopathic alkaloid produced by grasses such as wheat, barley and reed bamboo during the evolution process (Phytochemistry, 1984, 23(3), 539–541; Phytochemistry, 1985, 24(5),945–947; Exp.Appl.,1986,40(3),259–262.), has growth inhibitory effect on environmental plants, insects, microorganisms, etc. (Journal of Shaoyang University, 2003,2(2) , 131–135.). People...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/14A01N43/38A01P1/00A01P3/00C07C51/41C07C59/01C07C59/64C07C309/04C07C303/32C07C63/06
CPCA01N43/38C07D209/14
Inventor 卢爱党杨珊王铁男李红岩汪清民
Owner HEBEI UNIV OF TECH
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