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Application of 4-oxo-2-crotonamide derivative to preparation of bacteriostatic agents

A crotyl amide and oxo technology, which is used in the preparation of carboxylic acid amides, the preparation of organic compounds, and the active ingredients of amides, can solve problems such as threats to human life and health

Active Publication Date: 2017-06-20
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The threat of drug-resistant bacteria is unpredictable and seriously endangers human life and health

Method used

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  • Application of 4-oxo-2-crotonamide derivative to preparation of bacteriostatic agents
  • Application of 4-oxo-2-crotonamide derivative to preparation of bacteriostatic agents
  • Application of 4-oxo-2-crotonamide derivative to preparation of bacteriostatic agents

Examples

Experimental program
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Effect test

preparation example Construction

[0067] Specifically, the synthesis method may include the following steps:

[0068] (1) Formula (II) compound and glyoxylic acid generate formula (III) compound;

[0069] (2) the compound of formula (III) is condensed with an amine compound to obtain a compound of formula (I);

[0070] Wherein, in the step (1), the reaction condition is to use glacial acetic acid as the reaction solvent, and reflux reaction under the action of a catalytic amount of concentrated sulfuric acid to prepare the compound (III).

[0071] Wherein, in step (2), the reaction conditions are that compound (III) uses anhydrous dichloromethane as a solvent, first reacts with isobutyl chloroformate to generate a mixed anhydride, and then condenses with an amine compound to obtain compound (I); Or compound (III) is activated by carbodiimide condensing agent 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide with N,N-dimethylformamide as solvent, and then Condensation with amine compounds to obtain compound (I). ...

Embodiment 1

[0072] Embodiment 1, the synthesis of (E)-4-oxo-4-(1,1'-biphenyl)-2-butenamide (abbreviation I-1 or 4ph5) 1) β-bibenzoyl acrylic acid (abbreviation III-1) synthesis

[0073] In the 500mL reaction flask, add 4-biphenyl ethyl ketone (abbreviation II-1) (62.48g, 0.318mol), glyoxylic acid monohydrate (28.85g, 0.313mol), the acetic acid (250mL) of concentration 98% and concentration 98 % concentrated sulfuric acid (1mL), stirred, the material could not be completely dissolved, stirred and heated to 115 ° C, refluxed for about 0.5h, the reaction system was a yellow clear liquid, continued to react at the same temperature until the basic reaction of the raw materials was complete (TLC detection), after the reaction Evaporate acetic acid under reduced pressure, a large amount of white solid precipitated, add petroleum ether:ethyl acetate (volume ratio 2:1, 50mL), stir at room temperature for 0.5h, filter with suction, and dry under vacuum at 40°C to obtain the off-white solid product ...

Embodiment 2

[0079] Example 2, (E)-4-oxo-4-(1,1'-biphenyl)-N,N-dimethyl-2-butenamide (I-2) (referred to as 4ph5-2) Synthesis

[0080] Into the 200mL round bottom flask, add the β-bibenzoyl acrylic acid prepared in Example 1 (abbreviation III-1) (6.68g, 26.48mmol), anhydrous N,N-dimethylformamide (DMF, 30mL ), 1-hydroxybenzotriazole (HOBt, 4.29g, 31.77mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 10.15g, 52.96mmol ), electromagnetically stirred at room temperature to obtain a brown suspension A. Take another 25mL round bottom flask, add dimethylamine hydrochloride (3.0g, 36.79mmol), 5mL anhydrous DMF, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 2.59g, 31.78mmol), electromagnetically stirred at room temperature to obtain a colorless solution B. After 2h, the colorless solution B was added to the brown suspension A, followed by TLC, and the reaction was basically complete after 24h. It was quenched by adding 100 mL of water, extracted three times with 250 mL of di...

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Abstract

The invention discloses application of a 4-oxo-2-crotonamide derivative to preparation of bacteriostatic agents. The structure of the 4-oxo-2-crotonamide derivative is shown as a formula (I). The 4-oxo-2-crotonamide derivative has a bacteriostatic effect; good antibacterial activity can be realized on methicillin-resistant staphylococcus aureus, methicillin-resistant staphylococcus epidermidis, vancomycin drug-resistant enterococcus faecalis, vancomycin drug-resistant enterococcus faecium, methicillin-sensitive staphylococcus aureus, methicillin-sensitive staphylococcus epidermidis, vancomycin-sensitive enterococcus faecalis and vancomycin-sensitive enterococcus faecium. The formula I is shown in the description.

Description

technical field [0001] The invention relates to the application of 4-oxo-2-butenamide derivatives in the preparation of antibacterial agents. Background technique [0002] The situation of bacterial drug resistance is becoming increasingly serious, and the types and numbers of drug-resistant bacteria are increasing rapidly. Drug-resistant bacterial infection has become a serious problem in clinical anti-infection treatment. The fatality rate of drug-resistant bacterial infections is 11.7%, which is more than double that of common infections. The medical expenses of drug-resistant bacterial infections have risen sharply, more than three times higher than that of general infections, and the annual loss is tens of billions. The threat of drug-resistant bacteria is unpredictable and seriously endangers human life and health. [0003] Clinical Gram-positive pathogenic bacteria mainly include: Staphylococcus aureus (Staphylococcus aureus), including Methicillin-resistant Staphylo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/165A61K31/16A61P31/04C07C231/02C07C235/76C07D317/60
CPCA61K31/16A61K31/165C07C235/76C07D317/60
Inventor 余利岩王菊仙游雪甫王玉成任金凤赵莉莉王浩胡辛欣聂彤颖
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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