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Oxazolone compound with bactericidal effect, and preparation method thereof

A compound, the technology of oxazolone, which is applied in the field of oxazolone compounds and their preparation, can solve the problems of difficult clinical treatment and difficult to effectively control the infection of new drug-resistant bacteria, and achieve good antibacterial effect

Inactive Publication Date: 2020-08-21
THE FIRST AFFILIATED HOSPITAL OF HENAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the problem of drug resistance of multidrug-resistant bacteria is particularly prominent, which brings great difficulties to clinical treatment.
Facing the vicious cycle of "drug resistance-new drug development-drug resistance", and the existing drugs are still difficult to effectively control the infection of new drug-resistant bacteria, medicinal chemists are working hard to develop new drugs against drug-resistant bacteria, design and screen new drugs with new New antibacterial drugs with unique structures, unique mechanisms of action or new targets, or hybrid drugs with other drugs

Method used

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  • Oxazolone compound with bactericidal effect, and preparation method thereof
  • Oxazolone compound with bactericidal effect, and preparation method thereof
  • Oxazolone compound with bactericidal effect, and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0023]

[0024] In a reaction flask with a water separator, add 13.5g of 3-hydroxyacetophenone into 150mL of toluene, stir and dissolve, add 12g of 4-methylbenzaldehyde and 11g of sodium methoxide, and slowly raise the temperature to reflux. The water generated during the reaction was discharged through the water separator. After 3 hours of reaction, TLC monitored the complete reaction of the raw materials. Under vacuum conditions, 50 mL of toluene was evaporated under reduced pressure, and then the reaction liquid was poured into 200 mL of water, and the pH of the reaction liquid was adjusted to medium properties, and then extracted 3 times with dichloromethane 100mL, combined the organic phases, and separated and purified by silica gel column chromatography to obtain 1-(3-hydroxyphenyl)-3-(tolyl)-2-enyl-1-ketone 18.1 g; LC-MS (ESI): m / z 239 [M+H] + .

Embodiment 2

[0026]In a reaction flask with a water separator, add 13.5g of 3-hydroxyacetophenone into 150mL of toluene, stir and dissolve, add 12g of 4-methylbenzaldehyde and 5.5g of sodium methoxide, slowly raise the temperature to reflux, during the reflux reaction process Drain the moisture generated in the reaction process through the water separator, keep the reflux reaction for 11h, distill 50mL of toluene under reduced pressure under vacuum conditions, then pour the reaction solution into 200mL of water, adjust the pH of the reaction solution to be neutral by dilute hydrochloric acid, and then use Dichloromethane 100mL was extracted 3 times, and the organic phases were combined, and then separated and purified by silica gel column chromatography to obtain 9.4g of 1-(3-hydroxyphenyl)-3-(tolyl)-2-enyl-1 ketone; LC- MS(ESI):m / z 239[M+H] + .

Embodiment 3

[0028] In the reaction flask, add 13.5g of 3-hydroxyacetophenone into 200mL of methanol, stir and dissolve, add 12g of 4-methylphenylacetaldehyde and 11.5g of potassium hydroxide, slowly raise the temperature to reflux, and concentrate the reaction solution after reflux reaction for 15h , after adding water 250mL, extracted several times with ethyl acetate 50mL, combined the organic phases, washed with saturated brine, concentrated and separated by silica gel column chromatography to obtain compound 1-(3-hydroxyphenyl)-3-(tolyl )-2-enyl-1-ketone 14.5g; LC-MS (ESI): m / z 239[M+H] + .

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Abstract

The invention discloses an oxazolone compound with bactericidal activity, and a preparation method thereof, and belongs to the technical field of synthesis of antibacterial drugs. The oxazolone compound is characterized in that the oxazolone compound has a structure shown in the description. 3-hydroxyacetophenone and 4-methylbenzaldehyde which are used as initial raw materials undergo a four-stepreaction to obtain the oxazolone compound with the novel structure, the synthesis method is simple, and the reaction yield is very high. An antibacterial activity test is carried out through an oxfordcup agar diffusion method, it is found that the inhibition effect of the target compound on Escherichia coli is much better than that of bixicillin, the inhibition effect on Staphylococcus aureus isclose to that of bixicillin, and the target compound has the potential of serving as a broad-spectrum antibacterial drug.

Description

technical field [0001] The invention belongs to the technical field of antibacterial drug synthesis, and in particular relates to an oxazolone compound with bactericidal effect and a preparation method thereof. Background technique [0002] Since the discovery of penicillin in 1928, antibiotics have been commonly used in clinical treatment of various diseases. While the variety and quantity of antibiotics are being introduced, under the influence of various human and objective factors, the difficulty of drug selection, drug overdose, abuse, etc. have increased, and serious drug resistance has emerged in both Gram-positive and Gram-negative bacteria. In addition, bacteria acquired exogenous drug-resistant genes through horizontal transfer also accelerated the generation of drug-resistant strains. In 2006, Science published a report that a strain of Staphylococcus aureus preserved in the laboratory in 1930 was sensitive to antibiotics currently used clinically, while a strain...

Claims

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Application Information

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IPC IPC(8): C07D263/38A61P31/04
CPCA61P31/04C07D263/38Y02A50/30
Inventor 赵智伟李洋洋漫彦文冯海瑕陈晓杰李小莉
Owner THE FIRST AFFILIATED HOSPITAL OF HENAN UNIV OF SCI & TECH
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