Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of preparation method of bacterial inhibitor coumarin [3,4] abenzothiophene compound

A bacterial inhibitor, benzothiophene technology, applied in the field of preparation of bacterial inhibitor coumarin [3,4] abenzothiophene compounds, can solve the problem of limited application range, low reaction efficiency, many reaction steps, etc. question

Active Publication Date: 2021-08-24
诸暨市人民医院
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reported preparation methods of coumarin[3,4]abenzothiophene compounds are mainly obtained through oxidative coupling, which has the disadvantages of many reaction steps, low reaction efficiency and limited application range.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of preparation method of bacterial inhibitor coumarin [3,4] abenzothiophene compound
  • A kind of preparation method of bacterial inhibitor coumarin [3,4] abenzothiophene compound
  • A kind of preparation method of bacterial inhibitor coumarin [3,4] abenzothiophene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the preparation of 4a product

[0041] At room temperature, in a 25mL round bottom flask, add 5mmol of 2-hydroxycinnamaldehyde compound 1a, 5mmol of chlorobenzene compound 2a, 6mmol of elemental sulfur 3 respectively, and then add ethanol aqueous solution (H 2 O / EtOH=1:1, v / v) 15mL, 0.5mmol iron bromide, stirred at 90°C for 10 hours. After cooling, add 15 mL of saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, dry with anhydrous magnesium sulfate, evaporate the solvent, perform 200-300 mesh silica gel column chromatography, The mobile phase petroleum ether: acetone eluted to obtain the pure product of coumarin[3,4]abenzothiophene compound 4a (yield 95%, light yellow solid). 4a 1 H-NMR spectrum see figure 1 , 4a 13 C-NMR spectrum see figure 2 .

[0042] 1 H NMR (500MHz, CDCl 3 ):δ8.15(dd,J 1 =2.4Hz,J 2 =6.6Hz,1H),8.05(dd,J 1 =1.5Hz,J 2 =7.8Hz,1H),7.68(dd,J ...

Embodiment 2

[0046] Embodiment 2: Preparation of 4b product

[0047] At room temperature, in a 25mL round-bottomed flask, add 5mmol of 2-hydroxycinnamaldehyde compound 1a, 5mmol of 3-methylchlorobenzene compound 2b, 6mmol of elemental sulfur 3, and then add ethanol aqueous solution (H 2 O / EtOH=1:1, v / v) 15mL, 0.5mmol iron bromide, stirred at 90°C for 10 hours. After cooling, add 15 mL of saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, dry with anhydrous magnesium sulfate, evaporate the solvent, perform 200-300 mesh silica gel column chromatography, The mobile phase petroleum ether: acetone eluted to obtain the pure product of coumarin[3,4]abenzothiophene compound 4b (yield 94%, light yellow solid). 4b 1 H-NMR spectrum see image 3 , 4b 13 C-NMR spectrum see Figure 4 .

[0048] 1 H NMR (500MHz, CDCl 3 ):δ7.98(m,3H),7.91(s,1H),7.55-7.61(m,2H),7.52(d,J=8.5Hz,1H),7.49(s,1H),7.47(s, 1H), 7.44(s,...

Embodiment 3

[0052] Embodiment 3: Preparation of 4c product

[0053] At room temperature, in a 25mL round bottom flask, add 5mmol of 6-methyl-2-hydroxycinnamaldehyde compound 1b, 5mmol of chlorobenzene compound 2a, 6mmol of elemental sulfur 3, and then add ethanol aqueous solution ( h 2 O / EtOH=1:1, v / v) 15mL, 0.5mmol iron bromide, stirred at 90°C for 10 hours. After cooling, add 15 mL of saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, dry with anhydrous magnesium sulfate, evaporate the solvent, perform 200-300 mesh silica gel column chromatography, The mobile phase petroleum ether: acetone eluted to obtain the pure product of coumarin[3,4]abenzothiophene compound 4c (yield 91%, light yellow solid). 4c 1 H-NMR spectrum see Figure 5 , 4c 13 C-NMR spectrum see Image 6 .

[0054] 1 H NMR (500MHz, CDCl 3 ):δ8.07-8.18(m,1H),7.80(br s,1H),7.59-7.70(m,1H),7.32-7.51(m,4H),2.48(s,3H);

[0055] 13 ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method of a bacterial inhibitor coumarin[3,4]abenzothiophene compound. The preparation method is: a 2-hydroxycinnamaldehyde compound represented by formula (I), The halogenated benzene compounds shown and the elemental sulfur shown in formula (III), with ferric bromide (FeBr 3 ) as catalyst, ethanol aqueous solution (H 2 O-EtOH=1:1) is a solvent, and 1,8-diazabicycloundec-7-ene (DBU) is fully reacted under the action of a base, and the product is obtained by post-processing coumarin [3 ,4] Abenzothiophene compounds. The invention has the advantages of high catalytic efficiency, low substrate cost, non-toxic and cheap solvent, low requirement on equipment, excellent yield and the like.

Description

technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical intermediates, and in particular relates to a preparation method of a bacterial inhibitor coumarin [3,4]abenzothiophene compound. Background technique [0002] Bacteria are the most numerous of all organisms, mainly spherical, rod-shaped, and helical. Bacteria also have a great impact on human activities. Bacteria are the pathogens of many diseases, and can spread diseases among normal human bodies through various ways, such as contact, digestive tract, respiratory tract, insect bites, etc., which are highly contagious and extremely harmful to society. Bacterial inhibitors, also known as bacteriostatic agents, refer to substances that inhibit bacterial reproduction. After the substance acts on the bacteria, in most cases, it is between the limit concentration of sterilization and inhibition of its proliferation. At the intermediate concentration, the bacteria neither die no...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 徐锦骆方军
Owner 诸暨市人民医院