Coumarin-thiazole-indolone compounds, and preparation method and application thereof

An indolinone type, compound technology, applied in the directions of organic chemistry, medical preparations containing active ingredients, antibacterial drugs, etc., can solve problems such as difficult treatment of infectious diseases, and achieve the effect of good inhibition and killing activity

Inactive Publication Date: 2015-08-12
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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  • Coumarin-thiazole-indolone compounds, and preparation method and application thereof
  • Coumarin-thiazole-indolone compounds, and preparation method and application thereof
  • Coumarin-thiazole-indolone compounds, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of 3-acetyl-2H-benzopyran-2-one

[0026]

[0027] Put salicylaldehyde (1.22g, 10 mmol), ethyl acetoacetate (2.6g, 20 mmol), piperidine (0.5 mL) in a round bottom flask, add ethanol 100 mL, reflux for 12 hours, TLC shows that the reaction Complete, stop the reaction, cool to room temperature, add 300 mL of water, extract with ethyl acetate (200 mL×3), combine the organic phases, dry over anhydrous sodium sulfate, filter, spin dry, separate and purify through a silica gel column to obtain a yellow solid powder 1.5 g, yield 79%. 1 H NMR (CDCl 3 , 400 MHz) δ: 2.73 (s, 3H), 7.33-7.35 (m, 2H), 7.64-7.69 (m, 2H), 8.51 (s, 1H).

Embodiment 2

[0028] Example 2: Preparation of 3-(2-bromoacetyl)-2H-benzopyran-2-one

[0029]

[0030] 3-Acetyl-2H-chromen-2-one (188 mg, 1 mmol), p-toluenesulfonic acid (380 mg, 2 mmol), N-bromosuccinimide (354 mg, 2 mmol) in a round-bottomed flask, add 10 mL of DMF, react at 100 °C for 2 hours, TLC shows that the reaction is complete, stop the reaction, add saturated sodium thiosulfate solution, extract with ethyl acetate, combine the organic phases, and purify by silica gel column chromatography , to obtain 127 mg of white solid powder, yield 44%. 1 H NMR (CDCl 3 , 400 MHz) δ: 4.76 (s, 2H), 7.37-7.42 (m, 2H), 7.69-7.73 (m, 2H), 8.65 (s, 1H).

Embodiment 3

[0031] Example 3: Preparation of ethyl 4-(2-oxo-2H-benzopyran-3-yl)thiazole-2-carboxylate

[0032]

[0033] Put 3-(2-bromoacetyl)-2H-benzopyran-2-one (133 mg, 1 mmol), ethyl thiooxamide (399 mg, 3 mmol) in a round bottom flask, add 10 mL of methanol was stirred at room temperature for 24 hours. TLC showed that the reaction was complete. Stop the reaction, add 20 mL of water, extract with ethyl acetate, combine the organic phases, and purify by silica gel column chromatography to obtain 190 mg of tan solid powder with a yield of 63%. 1 H NMR (CDCl 3 , 400 MHz) δ: 1.49 (t, 3H), 4.51 (q, 2H), 7.32 (t, 1H), 7.38 (d, 1H), 7.58 (t, 1H), 7.66 (d, 1H), 8.74 ( s, 1H), 8.92 (s, 1H).

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Abstract

The invention discloses coumarin-thiazole-indolone compounds, and a preparation method and application thereof. The compounds are disclosed as Formula (I). The preparation method comprises the following steps: reacting salicylaldehyde and ethyl acetoacetate to obtain 3-acetyl-2H-benzopyranyl-2-one, carrying out bromination, cyclization and hydrazinolysis reaction to obtain 4-(2-oxo-2H-benzopyranyl-3-yl)thiazolyl-2-formylhydrazine, and finally, reacting with various substituted isatin to obtain the target compounds. The compounds can be used as a raw material of antibacterial drugs. The preparation method has the advantage of simple and accessible raw materials, and is convenient to operate.

Description

technical field [0001] The invention relates to a coumarin-thiazole-indolinone 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, is an endogenous active substance present in mammalian tissues and body fluids. In addition, the isatin structure also exists...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14A61K31/427A61P31/04
CPCC07D417/14
Inventor 王广成彭知云刘文超何典雄余健蒋杨洋
Owner JISHOU UNIVERSITY
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