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Emodin derivative and application thereof in preparing antibacterial agents

A technology of emodin and derivatives, which is applied in the field of medicine, can solve the problems of not too long clinical application time and increased drug resistance, and achieve good anti-drug-resistant bacteria effect

Inactive Publication Date: 2012-11-14
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Even newly marketed antibacterial drugs such as "quinupristin / dalfopristin" have been found to be resistant to some clinical isolates; and quinolones, which have not been clinically used for a long time, are widely used in China, making them resistant. Severely exacerbated drug levels

Method used

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  • Emodin derivative and application thereof in preparing antibacterial agents
  • Emodin derivative and application thereof in preparing antibacterial agents
  • Emodin derivative and application thereof in preparing antibacterial agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 4-chloro-1,3,8-trihydroxy-6-methyl-9,10-anthraquinone (3) and 4,7-dichloro-1,3,8-trihydroxy-6-methanol Synthesis of 9,10-anthraquinone (6), 4,5-dichloro-1,3,8-trihydroxy-6-methyl-9,10-anthraquinone (10)

[0024]

[0025] Take 4.46g (14.8mmol) of emodin, 300ml of anhydrous acetic acid, and 30ml of concentrated hydrochloric acid in an oil bath at 85°C and stir for 10 minutes, mix well, and then add 1.6ml (16mmol) of 30% hydrogen peroxide dropwise:

[0026] 1) Add 8 times in batches, slowly drop 200 μl each time, drop every 5 minutes. After the dropwise addition, continue to stir for 20 minutes to terminate the reaction. After the reaction liquid is cooled, add 250ml of water, and immediately a yellow precipitate is formed. It is filtered under reduced pressure and separated on a silica gel column to obtain compound 3 (4.02g, 13.22mmol, 89%)

[0027] 2) Add all at one time, continue to stir for 20 minutes after the dropwise addition, and then stop the reactio...

Embodiment 2

[0030] Example 2 Synthesis of 2-iodo-4-chloro-1,3,8-trihydroxy-6-methyl-9,10-anthraquinone (7)

[0031]

[0032] Take 0.8 g of 2-iodo-1,3,8-trihydroxy-6-methyl-9,10-anthraquinone (synthesized in our laboratory, see literature: Huang Wen, He Yang, Wu Xiaohua. Emodin derivatives and Its use [P]. Chinese patent: 201110230199, 2011-08-11, 2mmol), 60ml of anhydrous acetic acid, 10ml of concentrated hydrochloric acid in a 250ml round bottom flask, stir in an oil bath at 85°C for 10 minutes, mix well, then drop Add 300 μl of 30% hydrogen peroxide (add in 5 times, drop once every 5 minutes.) Stop the reaction for 20 minutes after the dropwise addition. After cooling, add 250ml of water and immediately find a yellow precipitate. Filter under reduced pressure and wash with water twice. Compound 7 (0.82 g, 90%) was obtained by vacuum filtration and drying.

[0033] Compound 7: 1 H NMR (400 MHz, DMSO) δ 13.83 (s, 1H), 11.67 (s, 1H), 7.45 (s, 1H), 7.16 (s, 1H), 2.42 (s, 3H).

Embodiment 3

[0034] Example 3 2,4,7-trichloro-1,3,8-trihydroxy-6-methyl-9,10-anthraquinone (4),

[0035] 2,4,5,7-Tetrachloro-1,3,8-trihydroxy-6-methyl-9,10-anthraquinone (5) and

[0036] Synthesis of 2,4,5-trichloro-1,3,8-trihydroxy-6-methyl-9,10-anthraquinone (8)

[0037]

[0038] Add 0.54g (2mmol) of emodin, 10ml of hydrochloric acid, 35ml of glacial acetic acid, and 0.82g (8mmol) of manganese dioxide into a 150ml round-bottomed flask in turn, and react at room temperature for about 15 minutes. After the plate reaction is complete, pour it into 200ml of water , precipitated at a high speed, filtered under reduced pressure, washed the filter cake twice with water to remove acetic acid, and separated by column to obtain compounds 4 (456mg, 1.22mmol, 61.0%), 5 (182mg, 0.45mmol, 22%) and 8 (84mg, 0.23mmol, 12%).

[0039] Compound 4: 1 H NMR (400 MHz, DMSO) δ 13.10 (s, 1H), 12.10 (s, 1H), 7.26 (s, 1H), 2.52 (s, 3H).

[0040] Compound 5: 1 H NMR (400MHz, CDCl 3 )δ12.90(s,1H), 12.85(s,...

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PUM

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Abstract

The invention relates to an emodin derivative and application thereof in preparing antibacterial agents. The chemical structural formula of the emodin derivative is represented as formula (I), wherein R1, R2, R3 and R4 are -F, -Cl, -Br, -I or -NO2; and R5, R6 and R7 are -H, -CH3, -CH2CH3 and -COCH3. The emodin derivative is a high-activity compound designed by performing structural modification on compounds with natural emodin as a matrix according to the principle of medical molecules. Experiments prove that the emodin derivative has good effects of resisting drug-resistance bacteria and superbacteria, the pharmaceutical effect of the emodin derivative is remarkably better than that of the emodin, and a new choice is provided for clinical medication.

Description

technical field [0001] The invention relates to emodin derivatives and uses thereof, belonging to the field of medicines. Background technique [0002] Since Fleming discovered penicillin in 1928, humans have discovered thousands of antibiotics. On the one hand, the birth of antibiotics has saved countless lives. On the other hand, with the widespread use of antibiotics, the problem of microbial resistance is becoming more and more serious. desperate situation. However, the discovery of new antibiotics has slowed down significantly in the past 40 years. Only a new structure of lipopeptide antibiotic daptomycin (daptomycin) has been successfully used clinically. It is urgent to develop new antibiotics to deal with the problem of drug resistance of pathogenic bacteria. [0003] Most of the antibacterial drugs in clinical use were discovered between 1936 and 1968. In the past 40 years, only three drugs with new antibacterial mechanisms have been discovered, namely linezolid, ...

Claims

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Application Information

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IPC IPC(8): C07C50/34C07C46/00A61K31/122A61P31/04A61P31/06
Inventor 陈谦明何杨黄文
Owner SICHUAN UNIV
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