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Preparing method of (E)-N'-arylmethylene-4-(coumarin-3-yl)thiazole-2-hydrazide compound and its application

A kind of technology of aryl methylene and compound, applied in (E)-N'-aryl methylene-4-(coumarin-3-yl)thiazole-2-hydrazide compound preparation method and application It can solve the problems of difficulty in the treatment of infectious diseases and achieve good inhibitory and killing effects

Inactive Publication Date: 2015-08-05
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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  • Preparing method of (E)-N'-arylmethylene-4-(coumarin-3-yl)thiazole-2-hydrazide compound and its application
  • Preparing method of (E)-N'-arylmethylene-4-(coumarin-3-yl)thiazole-2-hydrazide compound and its application
  • Preparing method of (E)-N'-arylmethylene-4-(coumarin-3-yl)thiazole-2-hydrazide compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Preparation of 3-acetyl-2H-benzopyran-2-one

[0024]

[0025] Put salicylaldehyde (1.22 g, 10 mmol), ethyl acetoacetate (2.6 g, 20 mmol), and piperidine (0.5 mL) in a round-bottomed flask, add 100 mL of ethanol, reflux for 12 hours, TLC shows the reaction After completion, 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, and 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

[0026] Embodiment two: the preparation of 3-(2-bromoacetyl)-2H-benzopyran-2-one

[0027]

[0028] 3-Acetyl-2H-benzopyran-2-one (188 mg, 1 mmol), p-toluenesulfonic acid (380 mg, 2 mmol), N-bromosuccinimide (354 mg, 2 mmol) was placed in a round-bottomed flask, 10 mL of DMF was added, and the reaction was carried out at 100 °C for 2 hours. TLC showed that the reaction was complete, and the reaction was stopped. Saturated sodium thiosulfate solution was added, extracted with ethyl acetate, the organic phases were combined, and purified by silica gel column chromatography , to obtain 127 mg of white solid powder with a yield of 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

[0029] Example 3: Preparation of ethyl 4-(2-oxo-2H-benzopyran-3-yl)thiazole-2-carboxylate

[0030]

[0031] 3-(2-Bromoacetyl)-2H-benzopyran-2-one (133 mg, 1 mmol), thiooxamide ethyl ester (399 mg, 3 mmol) were placed in a round bottom flask and added 10 mL of methanol was stirred at room temperature for 24 hours, TLC showed that the reaction was complete, the reaction was stopped, 20 mL of water was added, extracted with ethyl acetate, the organic phases were combined, and purified by silica gel column chromatography to obtain 190 mg of yellow-brown solid powder with a yield of 63%. 1 H NMR (CDCl 3 , 400 MHz) δ: 1.49 (t, 3H, J = 7.2 Hz), 4.51 (q, 2H, J = 7.2 Hz), 7.32 (t, 1H, J = 8.0 Hz), 7.38 (d, 1H, J = 7.2 Hz) 8.0 Hz), 7.58 (t, 1H, J = 8.0 Hz), 7.66 (d, 1H, J = 8.0 Hz), 8.74 (s, 1H), 8.92 (s, 1H).

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Abstract

The invention discloses a preparing method of (E)-N'-arylmethylene-4-(coumarin-3-yl)thiazole-2-hydrazide compound and its application. A formula (I) of the compound is shown as below. The preparing method includes: making salicylic aldehyde and ethyl acetoacetate into 3-acetylindole-2H-chromene-2-one, allowing bromization, cyclization and hydrazinolysis to obtain 4-(2-oxo-2H-chromene-3-yl)thiazole-2-hydrazine, and allowing the 4-(2-oxo-2H-chromene-3-yl)thiazole-2-hydrazine to react with substituted benzaldehydes to obtain the target compound. The compound can serve as a raw material for antiseptic medicine; the preparing method has the advantages that the raw materials are simple and easy to obtain and operating is convenient.

Description

technical field [0001] ( E )-N'-arylmethylene-4-(coumarin-3-yl)thiazole-2-hydrazide is ( E )-N'-arylmethylene-4-(2-oxo-2H-benzopyran-3-yl)thiazole-2-hydrazide, the present invention relates to ( E )-N'-arylmethylene-4-(2-oxo-2H-benzopyran-3-yl) thiazole-2-hydrazide compounds and their preparation method and application in the preparation of antibacterial drugs . Background technique [0002] With the wide application of antibacterial drugs, especially the abuse of antibiotics, the problem of drug resistance of bacteria around the world has become increasingly serious in recent years, and the trend is increasing 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 poses a serious threat to human life and health. [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04A61P31/04
CPCC07D417/04
Inventor 王广成彭知云何典雄刘文超余健蒋杨洋
Owner JISHOU UNIVERSITY
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