Broad-spectrum antibacterial benzamide compound and preparation method and application thereof

A benzamide and compound technology, applied in the field of 3,4-dichloro-N-benzamide and its preparation, can solve the problem of improvement of antibacterial activity without improvement, Clostridium difficile, no improvement of antibacterial activity, etc. problem, to achieve the effect of simple structure, huge development potential and good killing effect

Inactive Publication Date: 2020-10-16
SHANGHAI VETERINARY RES INST CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, Zhang Han et al. in my country (see literature: Synthesis of nitazoxanide derivatives and their antibacterial quantitative structure-activity relationship research, Chinese Academy of Agricultural Sciences, dissertation, 2012) synthesized two types of nitazoxanide derivatives (thiazoles and pyrimidines), the results showed that the minimum inhibitory concentration (MIC) of 7 compounds was less than or equal to 4μg / mL, but the tested bacteria were only anaerobic bacteria - Clostridium difficile
The compounds involved are mainly compounds with fluorine substitution on the benzene ring or trifluoromethane substitution. The drug synthesis cost is high, and the risk of environmental pollution is high, and the new compounds obtained do not improve the common aerobic or microbiological effects. Improvement of antibacterial activity of aerobic bacteria
Relevant reforms abroad mainly focus on the substitution of nitro on the thiazole ring and methylation on the benzene ring, but the obtained compounds also have no improvement in antibacterial activity against common aerobic or microaerophilic bacteria.

Method used

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  • Broad-spectrum antibacterial benzamide compound and preparation method and application thereof
  • Broad-spectrum antibacterial benzamide compound and preparation method and application thereof
  • Broad-spectrum antibacterial benzamide compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of 3,4-dichloro-N-(5-nitrothiazol-2-yl)benzamide (Formula I)

[0032] One-step synthesis. The target compound is synthesized by the reaction of acid chloride and heterocyclic (or phenyl) amine compound. Weigh about 3 mmol of 2-amino-5-nitrothiazole (Formula III), put it into a 100 mL three-necked flask, add 15 mL THF (tetrahydrofuran), stir magnetically until it is completely dissolved, take an ice-salt bath, and cool to 0 After adding 1.2 to 1.5 eq (equivalent) triethylamine. 3.6 mmol of 3,4-dichlorobenzoyl chloride (formula II) was dissolved in 5 mL of THF, and then slowly added dropwise into the reaction system through a constant pressure dropping funnel. After the dropwise addition, the ice bath was removed, and an appropriate amount of DMAP (p-dimethylaminopyridine) was added after the reaction for half an hour. Use petroleum ether: ethyl acetate as a developer, monitor the reaction by thin-layer chromatography until there is no raw materi...

Embodiment 2

[0034] Example 2: Antibacterial application of 3,4-dichloro-N-(5-nitrothiazol-2-yl)benzamide (Formula I)

[0035] The minimum inhibitory concentration (MIC) value of the target derivative compound was determined by the microbroth dilution method recommended by the Clinical and Laboratory Standards Institute (CLSI) VET01-A4.

[0036] The bacteria used in the examples include quality control strains and clinical isolates. The quality control strains: Escherichia coli (ATCC25922) and Staphylococcus aureus (ATCC25923) are preserved by our laboratory. Bacillus cereus (CVCC2002), Pasteurella multocida (CVCC469), and Streptococcus equine (CVCC556) were purchased from the strain preservation bank of China Veterinary Drug Control Institute. Clinically isolated strains: Escherichia coli, Staphylococcus aureus, Salmonella, Klebsiella pneumoniae, Aeromonas, Enterococcus and other 35 strains of bacteria were isolated, identified and preserved by our laboratory.

[0037] The target product...

Embodiment 3

[0044] Example 3: Inhibitory effect of 3,4-dichloro-N-(5-nitrothiazol-2-yl)benzamide (formula I) on bacterial growth and reproduction

[0045] Bacillus cereus (CVCC2002), Staphylococcus aureus ( S. aureus 3) For the test strain, take 10 5 The concentration of cfu / mL bacterial solution is the initial experimental bacterial concentration. After adding different concentrations of 3,4-dichloro-N-(5-nitrothiazol-2-yl)benzamide (Formula I) and NTZ, at 37 After culturing in a shaker at 180 rpm at 180 °C, 1 mL was taken every 1.5 h to measure the OD values ​​of different concentrations of bacterial solutions at 630 nm, and three replicates were set up to calculate the average value of OD. The antibacterial growth curve was drawn with time as the abscissa and OD value as the ordinate.

[0046] from Figure 1-4 As can be seen from the results in: before 7.5h, 2 µg / mL of 3,4-dichloro-N-(5-nitrothiazol-2-yl)benzamide (formula I) has always been effective against Bacillus cereus Very...

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Abstract

The invention provides a benzamide new compound with activity of resisting multiple bacteria anda preparation method and application thereof. The compound is 3, 4-dichloro-N-(5-nitrothiazole-2-yl) benzamide, the compound is small in molecular weight, relatively simple in structure and easy to synthesize and obtain, antibacterial experiments prove that the compound has the advantages of being highin inhibition performance, good in killing effect and the like, and common aerobic or microaerobic bacteria such as staphylococcus aureus, salmonella and enterococcus can be remarkably inhibited. Meanwhile, the growth and the propagation of bacteria can be effectively inhibited for a long time. Therefore, the compound has huge development potential in the antibacterial aspect.

Description

technical field [0001] The present invention relates to compounds and their synthesis and application. Specifically, the present invention relates to a new benzamide compound with activity against various bacteria and its preparation method and application. More specifically, it relates to 3,4-dichloro -N-(5-nitrothiazol-2-yl)benzamide and its preparation method and use. Background technique [0002] With the continuous emergence of antibacterial drugs in the 20th century, some bacterial infectious diseases that were originally difficult to treat in the past are no longer terminal diseases. However, with the continuous advent of antibacterial drugs and their wide application worldwide, the resistance of bacteria to antibiotics has become increasingly prominent, and has developed into a serious public health problem by the end of the 1980s. For example: Methicillin-Resistant Staphylococcus aureus (MRSA) has become a common pathogen of serious infections in hospitals; drug-re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/46A61P31/04A61K31/426A01N43/78A01P1/00A61K8/49A61Q11/00
CPCC07D277/46A61P31/04A01N43/78A61K8/49A61Q11/00Y02A50/30
Inventor 张可煜王霄旸王春梅郑海红王满梅费陈忠张丽芳王艳平江雪佳
Owner SHANGHAI VETERINARY RES INST CHINESE ACAD OF AGRI SCI
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