3-nitro-2h-chromene compounds with antibacterial activity and preparation method and application thereof

The technology of a compound and a nitro group is applied in the field of 3-nitro-2H-chromene compound and its preparation, which can solve the problems of prolonging the treatment time of patients, increasing the mortality rate and the like, and achieving the effect of simple reaction steps.

Inactive Publication Date: 2011-08-17
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The emergence and spread of these drug-resistant bacteria has brought serious problems to the treatment of bacterial infectious diseases, resulting in prolonged treatment time and increased mortality for patients

Method used

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  • 3-nitro-2h-chromene compounds with antibacterial activity and preparation method and application thereof
  • 3-nitro-2h-chromene compounds with antibacterial activity and preparation method and application thereof
  • 3-nitro-2h-chromene compounds with antibacterial activity and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: 3-nitro-2H-chromene

[0020] In a 250mL three-neck round bottom flask, add salicylaldehyde (0.488g, 4mmol), dibutylamine (0.260g, 2mmol), phthalic anhydride (1.184g, 8mmol) and toluene (25ml), and then load Dean-Stark water splitter. 2-Nitroethanol (0.364 g, 4 mmol) was added slowly (12 hours) with an automatic syringe pump, and the reaction mixture was stirred and refluxed for 24 hours. Then 2-nitroethanol (0.364 g, 4 mmol) was added slowly (12 hours), and the reaction mixture was refluxed for 24 hours. After removing the solvent under reduced pressure, the crude product was purified by silica gel column chromatography (petroleum ether / dichloromethane gradient elution) to obtain 0.324 g of a yellow solid product, namely 3-nitro-2H-chromene, with a yield of 45.8% and a melting point of 77.0 -78.0°C. The characterization parameters of 3-nitro-2H-chromene are as follows:

[0021] 1 H NMR (400MHz, CDCl 3 )δ: 7.79(s, 1H), 7.37-7.32(m, 1H), 7.26(dd, J=7.6, 1...

Embodiment 2

[0023] Example 2: 3-nitro-6-chloro-2H-chromene

[0024] In a 250mL three-neck round bottom flask, add 5-chloro-2-hydroxybenzaldehyde (0.626g, 4mmol), n-Bu 2 NH (0.260 g, 2 mmol), phthalic anhydride (1.184 g, 8 mmol), and toluene (25 ml) were fitted with a Dean-Stark trap. 2-Nitroethanol (0.364 g, 4 mmol) was added slowly (12 hours) with an automatic syringe pump, and the reaction mixture was stirred and refluxed for 24 hours. Then 2-nitroethanol (0.364 g, 4 mmol) was added slowly (12 hours), and the reaction mixture was refluxed for another 24 hours. After removing the solvent under reduced pressure, the crude product was purified by silica gel column chromatography (petroleum ether / dichloromethane gradient elution) to obtain 0.372 g of 3-nitro-6-chloro-2H-chromene as a yellow solid, with a yield of 44.0% , melting point: 109.5-110.4°C.

[0025] 1 H NMR (400MHz, CDCl 3 )δ: 7.71(s, 1H), 7.29(dd, J=8.7, 2.5Hz, 1H), 7.24(d, J=2.5Hz, 1H), 6.87(d, J=8.7Hz, 1H), 5.26( d, J=1.1...

Embodiment 3

[0027] Example 3: 3-nitro-6-fluoro-2H-chromene

[0028] In a 250mL three-neck round bottom flask, add 5-fluoro-2-hydroxybenzaldehyde (0.560g, 4mmol), dibutylamine (0.260g, 2mmol), phthalic anhydride (1.184g, 8mmol) and toluene (25ml), and then install the Dean-Stark water separator. 2-Nitroethanol (0.364 g, 4 mmol) was added slowly (12 hours) with an automatic syringe pump, and the reaction mixture was stirred and refluxed for 24 hours. Then 2-nitroethanol (0.364 g, 4 mmol) was added slowly (12 hours), and the reaction mixture was refluxed for 24 hours. After removing the solvent under reduced pressure, the crude product was purified by silica gel column chromatography (petroleum ether / dichloromethane gradient elution) to obtain 0.367 g of orange solid, namely 3-nitro-6-fluoro-2H-chromene, yield 47.1 %, 85.5-86.5°C.

[0029] 1 H NMR (400MHz, CDCl 3 )δ: 7.72(s, 1H), 7.07-7.02(m, 1H), 6.98(dd, J=7.8, 3.0Hz, 1H), 6.89(dd, J=8.9, 4.4Hz, 1H), 5.23(d , J=1.0Hz, 2H); 13 C NMR ...

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Abstract

The invention discloses 3-nitro-2H-chromene compounds, a preparation method and application thereof. The 3-nitro-2H-chromene compounds have a novel antimicrobial parent nucleus structure, are prepared by reacting salicylaldehyde or substituted salicylaldehyde, n-Bu2NH, phthalic anhydride and 2-nitroethanol, and can be used for preparing medicaments for treating infectious diseases, particularly can be used for preparing medicaments for treating infectious diseases caused by multidrug-resistant bacteria.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a 3-nitro-2H-chromene compound with antibacterial activity, a preparation method and application thereof. Background technique [0002] Antibiotics, sulfonamides, and quinolones are used to treat bacterial infectious diseases, but with the widespread use of these drugs, bacteria have developed resistance to these drugs, and even multidrug resistance. For example, methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus epidermidis (MRSE), drug-resistant Streptococcus pneumoniae, vancomycin-resistant Enterococcus (VRE) and Staphylococcus aureus (VRSA), etc. The emergence and spread of these drug-resistant bacteria has brought serious problems to the treatment of bacterial infectious diseases, resulting in prolonged treatment time and increased mortality for patients. Therefore, it is of great significance to develop new structures and drugs with non-traditional ant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/58A61K31/352A61P31/00
Inventor 鄢明肖国强殷霞
Owner SUN YAT SEN UNIV
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