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Application of perylene tetracarboxylic dianhydride amidation compound in anti-staphylococcus aureus

A technology of tetracarboxylic dianhydride amide and perylene tetracarboxylic dianhydride, which is applied in the fields of antibacterial drugs and organic chemistry, can solve the problems of limited antibacterial effect, achieve compound stability, simple preparation, and the effect of inhibiting the growth of Staphylococcus aureus

Inactive Publication Date: 2019-08-23
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Natural antibacterial materials come from natural plants with good biocompatibility but limited antibacterial effect

Method used

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  • Application of perylene tetracarboxylic dianhydride amidation compound in anti-staphylococcus aureus
  • Application of perylene tetracarboxylic dianhydride amidation compound in anti-staphylococcus aureus
  • Application of perylene tetracarboxylic dianhydride amidation compound in anti-staphylococcus aureus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] This example proposes a compound against Staphylococcus aureus: PDI-ACI, which has the following molecular structural formula:

[0063]

[0064] The preparation method of this compound is as follows:

[0065] Dissolve tetrachloroperylene anhydride and N,N-dimethylethylenediamine at a ratio of 1:16 (tetrachloroperylene anhydride 1 mmol, N,N-dimethylethylenediamine 16 mmol) in N-methylpyrrolidone (30 ml) and glacial acetic acid (15 ml) were reacted at 120 °C, followed by argon for 10 min and heated for 24 h. After the completion, add 60 ml of 2 mol / L hydrochloric acid and 60 ml of absolute ethanol, stir vigorously, put it in the refrigerator to stand still, suction filter after 24 h, wash with ethanol, and dry in vacuum to obtain the product and methyl iodide in a ratio of 1:8 ( The former (0.15 mmol, the latter 1.2 mmol) was dissolved in 8 ml of toluene, argon was passed through for 10 min at 85°C, and then heated to reflux for 12 h. After the reaction was completed,...

Embodiment 2

[0069] This embodiment proposes a compound against Staphylococcus aureus: PDI-I, which has the following molecular structural formula:

[0070] .

[0071] PDI-I preparation method is as follows:

[0072] 3,4,9,10-Perylenetetracarboxylic dianhydride (1 mmol; compared with tetrachloroperylene anhydride, which has 4 more chlorine atoms in the alkyl position), N,N-dimethylethylene di Amine (10 mmol)) and glacial acetic acid (10 ml) were sequentially added to N,N-dimethylpyrrolidone (NMP, 20 ml) and reacted at 120 °C for 24 h under the protection of argon. Cool the reacted mixture to room temperature, add 50 ml each of absolute ethanol and 2M HCl, stir with a glass rod, let it stand, filter, dry in vacuo, and refine by column chromatography (mobile phase: trichloromethane (CHCl 3 )), to obtain red solid PDI-I. Then PDI-I (0.188 mmol) and iodomethane (CH 3 I, 1.502 mmol) was added to toluene (8 ml), heated to reflux at 85°C for 9h. Then add diethyl ether to precipitate, filte...

Embodiment 3

[0074] This example proposes a compound against Staphylococcus aureus: PDI-2Br, which has the following molecular structural formula: ,

[0075] The preparation method of PDI-2Br is as follows:

[0076] Dissolve 1 mmol of dibromoic anhydride and 1.8 ml of N,N-dimethylethylenediamine in quinoline (10 ml), react at 160 °C, first pass argon for 10 min, and heat for 24 h. Cool and suction filter, wash with methanol, and dry in vacuo to obtain the product N,N-dimethyl-dibromoperyleneimide. Take N,N-dimethyl-dibromoperyleneimide and methyl iodide at a ratio of 1:8 (for example, the former is 0.1 mmol, the latter is 0.8 mmol) and dissolved in 40 ml of toluene, first pass argon for 10 min, and then heat at 85°C Reflux for 12 h. After the reaction, cool, filter with suction, wash with ether three times, and dry in vacuum to obtain PDI-2Br.

[0077] application

[0078] Anti-Staphylococcus aureus application based on the compound described in Example 1:

[0079] 1) Prepare strains...

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Abstract

The invention provides an application of a perylene tetracarboxylic dianhydride amidation compound in anti-staphylococcus aureus. The compound is simple to prepare, a perylene tetracarboxylic dianhydride compound and N,N-dimethylethylenediamine are used as raw materials, multiple steps are carried out, the compound can inhibit the growth of staphylococcus aureus, and the bacteriostasis circle of the compound is up to about 10 mm measured by the K-B method. The compound is subjected to 2-fold gradient dilution, and the measured minimum inhibitory concentration (MIC) against staphylococcus aureus is up to 6.25 mg / mL. The growth curve inhibition test shows that when a growth curve of the bacteria in the non-drug treatment group enters the logarithmic phase, a growth curve of the bacteria in the compound treatment group is still in the lag phase, and indicates that the compound can inhibit the division of staphylococcus aureus. The discovered compound in the future can be used for the control of staphylococcus aureus infection, can also be applied in the preparation of antibacterial biomaterials, and has certain application value.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to the application of a perylenetetracarboxylic dianhydride amidated compound in anti-staphylococcus aureus. Background technique [0002] Characteristics, pathogenicity, drug resistance of Staphylococcus aureus. Staphylococcus aureus belongs to the genus Staphylococcus and is a Gram-negative bacterium that is pathogenic to humans. The nutritional requirements of this type of bacteria are not high, and ordinary medium can meet their needs, and the colonies on solid medium are golden yellow. In liquid medium, the bacterial solution is turbid. Capsular polysaccharides exist on the surface of most Staphylococcus aureus, which facilitate the adsorption of bacteria to human cells or the surface of biological materials (such as biological valves, catheters, joints, etc.). Staphylococci are more resistant to the external environment. Staphylococcus aureus can cause purulent infection...

Claims

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Application Information

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IPC IPC(8): C07D471/06A61P31/04
CPCA61P31/04C07D471/06
Inventor 卫文强黄永伟王优杨育育李文博
Owner HENAN UNIVERSITY
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