Dithiocarbamate compounds, and preparation method and application thereof

A technology of dithiocarbamate and compounds, applied in the field of chemical biology research, can solve the problems of unsuitable 5-aminopyrazole, interference reaction, high amino activity, etc.

Active Publication Date: 2020-02-28
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the amino activity of 5-aminopyrazole derivatives is high, which will interfere with the reaction. At present, there is no technical method for introducing dithiocarbamate on the 5-aminopyrazole heterocycle
In the past, we developed a dithiocarbamate reaction technology catalyzed by iodine and iron trifluoride, which effectively introduced dithiocarbamate fragments on imidazo heterocycles (Chinese patent, patent number: ZL201510524047. 2), but this technique is not suitable for the reaction of 5-aminopyrazole and indole
At present, the technical method of introducing dithiocarbamate fragments on indole adopts the reaction of non-commercialized and difficult-to-obtain expensive reagent indole magnesium reagent with thiuram, and this technical scheme is difficult to realize industrial production (Synlett, 2005 ,2691-2693)

Method used

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  • Dithiocarbamate compounds, and preparation method and application thereof
  • Dithiocarbamate compounds, and preparation method and application thereof
  • Dithiocarbamate compounds, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1. Synthesis of 5-amino-1-methyl-1H-pyrazol-4-yl-dimethylamino-dithiocarbamate (I-1).

[0049] The synthetic route is:

[0050]

[0051] Specifically include the following steps:

[0052] The compound of formula (1a), compound of formula (2a), potassium persulfate, and potassium iodide were mixed in a molar ratio of 1:1.5:2:0.2, wherein the compound of formula (a) was 2 mmol. The reaction system was stirred at 60°C for 12 hours. Cool after the reaction, add an appropriate amount of dichloromethane, extract with water, dry the organic phase, filter with suction, evaporate the filtrate, remove the solvent, and use silica gel column chromatography for the residue, rinse with petroleum ether, detect by TLC, and combine the effluent containing the product , the solvent was distilled off by a rotary evaporator, and the target product was obtained as a white solid by vacuum drying, with a yield of 61% and a purity of 99.5% (HPLC).

[0053] Compound I-1 physical c...

Embodiment 2

[0059] Example 2. Synthesis of 5-amino-1-methyl-3-phenyl-1H-pyrazol-4-yl-dimethylamino-dithiocarbamate (I-8).

[0060] The synthetic route is:

[0061]

[0062] Specifically include the following steps:

[0063] The above formula (1h) compound, formula (2a) compound, potassium persulfate, and potassium iodide were used in a molar ratio of 1:1.5:2:0.2, wherein the formula (1h) compound was 2 mmol. The reaction system was stirred at 60°C for 12 hours. Cool after the reaction, add an appropriate amount of dichloromethane, extract with water, dry the organic phase, filter with suction, evaporate the filtrate, remove the solvent, and use silica gel column chromatography for the residue, rinse with petroleum ether, detect by TLC, and combine the effluent containing the product , the solvent was distilled off by a rotary evaporator, and the target product was obtained as a white solid by vacuum drying, with a yield of 87% and a purity of 99.3% (HPLC).

[0064] Compound I-8 phys...

Embodiment 3

[0070] Example 3. Synthesis of 2-methyl-1H-indol-3-yl-dimethylamino-dithiocarbamate (II-2).

[0071]

[0072] Specifically include the following steps:

[0073] The above formula (3a) compound, formula (2a) compound, potassium persulfate, and potassium iodide were used in a molar ratio of 1:1.5:2:0.2, wherein the formula (3a) compound was 2 mmol. The reaction system was stirred at 60°C for 12 hours. Cool after the reaction, add an appropriate amount of dichloromethane, extract with water, dry the organic phase, filter with suction, evaporate the filtrate, remove the solvent, and use silica gel column chromatography for the residue, rinse with petroleum ether, detect by TLC, and combine the effluent containing the product , the solvent was distilled off by a rotary evaporator, and the target product was obtained as a white solid by vacuum drying, with a yield of 94% and a purity of 99.6% (HPLC).

[0074] Compound II-2 physical constants and characterization data are as fol...

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Abstract

The invention discloses dithiocarbamate compounds, and a preparation method and application thereof. The dithiocarbamate compounds disclosed by the invention comprise 5-aminopyrazole-dithiocarbamate,indole-dithiocarbamate and substituted benzene-dithiocarbamate. The dithiocarbamate compounds with structural formulas as shown in a formula I, a formula II and a formula III are respectively preparedthrough reactions of an aromatic hydrocarbon 5-aminopyrazole compound, an indole compound and a substituted benzene compound with an amino dithioformyl disulfide compound in a reaction solvent in thepresence of an oxidizing agent and an iodine reagent. The compounds have different degrees of antibacterial activity on Chinese rose anthracnose, Fusarium oxysporum, Fusarium proliferatum, Fusarium solani, Geotrichum candidum, Penicillium digitatum, Penicillium italicum, Phyricularia oryzae and the like.

Description

technical field [0001] The invention belongs to the field of chemical biology research, and in particular relates to a class of dithiocarbamate compounds and a preparation method and application thereof. Background technique [0002] Carbamate pesticides have the advantages of strong selectivity, wide insecticidal spectrum, synergists can be used to improve drug efficacy, low toxicity to humans, animals and fish, simple structure and easy synthesis. Dithiocarbamate compounds have been proved to have excellent biological activity. A large number of studies have shown that the splicing of dithiocarbamate fragments and nitrogen heterocycles has excellent biological activity ("Research Progress in Biological Activity of Carbadithiocarbamate Compounds", Applied Chemistry, 2015, 32(2), 123 -133), has obvious antitumor, antibacterial, antioxidative and insecticidal and other biological activities. In drug development, nitrogen-containing heterocycles including pyrazole, indole, p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/46C07D209/30C07D471/06C07D455/04C07C333/20A01N47/18A01N47/22A01P3/00
CPCA01N47/18A01N47/22C07C333/20C07D209/30C07D231/46C07D455/04C07D471/06
Inventor 汤日元黄卓斌张晓勇
Owner SOUTH CHINA AGRI UNIV
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