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Compound, pharmaceutical composition, medicine and application of compound, pharmaceutical composition and medicine in preparation of antibacterial products

A compound and solvate technology, applied in the application field of preparing antibacterial products, can solve problems such as adverse effects

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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] A variety of FtsZ inhibitors that have been reported so far have shown excellent antibacterial activity. The alkaloid compound sanguinarine has a moderate inhibitory effect on Gram-negative bacteria and Gram-positive bacteria, and has a broad spectrum of antibacterial activity, but It is also slightly inhibitory to tubulin in eukaryotic cells
Since tubulin plays an indispensable role in maintaining cell shape, movement, and intracellular material transportation, the above compounds may cause serious adverse effects on the body while exerting antibacterial effects

Method used

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  • Compound, pharmaceutical composition, medicine and application of compound, pharmaceutical composition and medicine in preparation of antibacterial products
  • Compound, pharmaceutical composition, medicine and application of compound, pharmaceutical composition and medicine in preparation of antibacterial products
  • Compound, pharmaceutical composition, medicine and application of compound, pharmaceutical composition and medicine in preparation of antibacterial products

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Embodiment 1: the preparation of 2-(anilino)benzoic acid (2)

[0067]

[0068] Weigh raw material 2-bromobenzoic acid (2.0g, 10mmol), aniline (1.85g, 20mmol), potassium carbonate (1.37g, 10mmol) and catalytic amount of copper powder (0.2-0.3 microns, 4.97mmol) and dissolve in 80mL in ethanol. The reaction solution was heated under reflux for 12 hours. After the reaction was monitored by TLC, the cooled reaction solution was poured into hot water, filtered through diatomaceous earth to remove insoluble matter, and then the filtrate was acidified with diluted hydrochloric acid solution to adjust the pH to 5-6, a large amount of precipitates were separated out, and the resulting precipitated product was purified by ethanol recrystallization to obtain 1.65 g of pure gray solid product, namely intermediate 2, with a yield of 78%.

Embodiment 2

[0069] Embodiment 2: Preparation of 9(10H)-acridone (3)

[0070]

[0071] The intermediate 2-(anilino)benzoic acid (2.0 g, 9.4 mmol) prepared in Example 1 above was put into a 100 mL round bottom flask, and 10 mL of concentrated sulfuric acid was added thereto. Stir the mixture under nitrogen protection at 100°C for 6 hours. After monitoring the complete reaction by TLC, cool to room temperature, and then pour the cooled reaction solution into a large amount of ice water and stir. After the solid precipitates, it is collected by suction filtration under reduced pressure. The solid was washed several times with sodium bicarbonate solution, and dried in vacuo to obtain 1.5 g of a yellow solid product, ie Intermediate 3, with a yield of 82%.

Embodiment 3

[0072] Embodiment 3: the preparation of 9-bromoacridine (4)

[0073]

[0074]The intermediate 9(10H)-acridone (4.0 g, 20.5 mmol) prepared in Example 2 above was weighed and placed in a 250 mL round bottom flask. Phosphorus tribromide (19.5 mL, 205 mmol) was injected dropwise in an ice bath at 0° C. under nitrogen protection. After the dropwise addition, the reaction solution was moved to 110° C. and stirred at this temperature for 24 hours. After the completion of the reaction was monitored by TLC, the reaction solution was cooled to room temperature, and then slowly added to water to quench the reaction. Then the filtrate was adjusted to pH 14 with sodium hydroxide solution, transferred to a separatory funnel, extracted three times with dichloromethane, the combined organic phase was washed twice with brine, dried over anhydrous sodium sulfate, filtered with suction, and extracted under reduced pressure Concentrate to obtain 3.81 g of a yellow solid product, ie Intermedi...

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Abstract

The invention particularly relates to a compound, a pharmaceutical composition, a medicine and application of the compound, the pharmaceutical composition and the medicine in preparation of antibacterial products. The seeking of a novel antibacterial target and the development of a novel chemical entity have important significance for solving the increasingly severe bacterial drug resistance problem at present, and the design of a compound entity acting on the FtsZ target is expected to be developed to obtain an antibacterial drug which has no influence on a host. The invention provides a 9-aralkyl-10-methylacridine quaternary ammonium salt derivative and a preparation method thereof, and the compound has significant bactericidal and / or bacteriostatic activity on gram-positive bacteria, has a good effect of inhibiting bacterial division protein FtsZ, and can be used for preparing antibacterial products.

Description

technical field [0001] The invention belongs to the technical field of antibacterial active compounds, in particular to a 9-arylalkyl-10-methylacridine quaternary ammonium salt derivative, comprising the 9-arylalkyl-10-methylacridine quaternary ammonium salt The pharmaceutical composition of derivatives, medicine and its application in the preparation of antibacterial products. Background technique [0002] Information in this background section is not necessarily to be taken as an acknowledgment or in any way to suggest that this information constitutes prior art. [0003] The discovery of antibacterial drugs is a milestone in the history of drug discovery. Most of the antibiotics used clinically have the characteristics of high efficiency and broad spectrum, and can effectively treat various diseases caused by a variety of common Gram-positive and Gram-negative bacteria infections. However, drug-resistant bacterial infections caused by the widespread use and abuse of anti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02A61P31/04A61K31/473A01N43/42A01P1/00
CPCC07D219/02A61P31/04A01N43/42
Inventor 马淑涛宋迪张楠
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