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Metronidazole-isatin type compound as well as preparation method and application thereof

A compound, isatin-type technology, applied in the field of metronidazole-isatin-type compound and its preparation method and application, can solve problems such as difficult treatment of infectious diseases, and achieve good inhibitory and killing effects

Inactive Publication Date: 2016-05-04
JISHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] With the wide application of antibacterial drugs, especially the abuse of antibiotics, the problem of bacterial resistance worldwide has become increasingly serious in recent years, and it is showing an increasing trend year by year, which brings great difficulties to the treatment of infectious diseases

Method used

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  • Metronidazole-isatin type compound as well as preparation method and application thereof
  • Metronidazole-isatin type compound as well as preparation method and application thereof
  • Metronidazole-isatin type compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-methylbenzenesulfonate

[0023]

[0024] Place metronidazole (10.00mmol), pyridine (35.0mL) and p-toluenesulfonyl chloride (20.00mmol) in a round bottom flask, stir and react at room temperature for 12h, TLC shows that the reaction is complete, stop the reaction, and pour the reaction solution into an appropriate amount of In water, off-white crystals were precipitated, filtered with suction, washed the filter cake with an appropriate amount of water, and dried to obtain a white solid powder 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-methyl Base benzene sulfonate, productive rate 69.5%. 1 HNMR(d 6 -DMSO, 400MHz): δ:2.40(s,3H),2.41(s,3H),4.39(t,2H),4.55(t,2H),7.39(d,2H),7.59(d,2H), 7.92(s,1H);EIMSm / z=326[M + ].

Embodiment 2

[0025] Example 2: Preparation of 4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)benzaldehyde

[0026]

[0027] P-Hydroxybenzaldehyde (2mmol), cesium carbonate (4mmol), 2-(2-methyl-5-nitro-1H-imidazol-1-yl) ethyl 4-methylbenzenesulfonate (2mmol) In a round bottom flask, add N,N-dimethylformamide (5mL), heat up to 90°C and react for 12h, TLC shows that the reaction is complete, stop the reaction, add water, extract 3 times with ethyl acetate, combine the extracts, Dry over anhydrous sodium sulfate, filter and spin dry, and the residue is separated by chromatography to obtain a yellow solid powder 4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy ) Benzaldehyde, 73% of productive rate. 1 HNMR(d 6 -DMSO,400MHz)δ:2.51(s,3H),4.48(t,2H),4.76(t,2H),7.01(d,2H),7.84(d,2H),8.04(s,1H),9.87 (s,1H);EIMSm / z=276[M + ].

Embodiment 3

[0028] Example 3: (E)-3-((E)-(4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)benzylidene)hydrazone base) preparation of indoline-2-one (1)

[0029]

[0030] Put isatin (10.00mmol) and hydrazine hydrate (11.00mmol) in a round-bottomed flask, add methanol (15.0mL), reflux for 3-8h, stop the reaction, cool to room temperature, filter the reaction solution with appropriate amount of methanol The filter cake was washed and dried to obtain 3-hydrazinoindolin-2-one as a yellow solid powder; the yield was 72%. 3-Diaminoindoline-2-one (1.00mmol), 4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)benzaldehyde (1.00 mmol) in a round-bottomed flask, add ethanol (6.0mL), glacial acetic acid (1 drop), heat up to reflux, react for 4-8h, TLC shows that the reaction is complete, stop the reaction, cool to room temperature, suction filter, and use an appropriate amount of ethanol The filter cake was washed to obtain a crude product, which was purified by silica gel column chromatography to ob...

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Abstract

The invention discloses a metronidazole-isatin type compound as well as a preparation method and an application thereof. The compound has a structure represented by a formula (I) (shown in the specification). The preparation method comprises the following steps: preparing 2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethyl-4-methyl benzenesulfonate from metronidazole and paratoluensulfonyl chloride serving as raw materials, and reacting by virtue of cesium carbonate serving as alkali, N,N-dimethyl formamide serving as a solvent and p-hydroxy benzaldehyde, so as to obtain 4-(2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethyoxyl)benzaldehyde; carrying out dehydration condensation on isatin, a derivative of isatin and hydrazine hydrate so as to obtain an intermediate, and carrying out dehydration condensation on the intermediate and 4-(2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethyoxyl)benzaldehyde in the presence of glacial acetic acid serving as a catalyst, so as to obtain the target product. The compound can be used as a raw material of antibacterial drugs; and in the preparation method, the raw materials are simple and easily available, and the operation is convenient.

Description

technical field [0001] The invention relates to a metronidazole-isatin type compound, its preparation method and its application in the preparation of antibacterial drugs. Background technique [0002] With the widespread application of antibacterial drugs, especially the abuse of antibiotics, the problem of bacterial resistance worldwide has become increasingly serious in recent years, and it is showing an increasing trend year by year, which brings great difficulties to the treatment of infectious diseases. In particular, the emergence of multidrug-resistant bacteria such as methicillin-resistant Staphylococcus aureus (MRSA), penicillin-resistant Streptococcus pneumoniae (PRSP), and multidrug-resistant Mycobacterium tuberculosis has seriously threatened human life and health. [0003] Isatin, also known as indolindione or 2,3-indoloquinone, exists in various natural products and is a common natural product structure. According to literature reports, isatin and its derivat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12A61K31/4178A61P31/04
CPCC07D403/12
Inventor 王广成彭知云李欣李涓
Owner JISHOU UNIVERSITY
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