Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

2-Substituted-3-arylmethanone-6-(5-methyl-2-phenyl-4-ethoxyoxazole)benzofuran compound

A technology of ethoxy oxazole and benzofuran, applied in organic chemistry, organic active ingredients, antibacterial drugs, etc., can solve problems such as toxic and side effects, and achieve excellent antibacterial activity

Inactive Publication Date: 2016-07-06
SHANGHAI JIAO TONG UNIV
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since most of the antibacterial drugs used clinically have severe side effects, the development of safe and efficient antibacterial compounds has become an important research direction for medicinal chemists

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
  • 2-Substituted-3-arylmethanone-6-(5-methyl-2-phenyl-4-ethoxyoxazole)benzofuran compound
  • 2-Substituted-3-arylmethanone-6-(5-methyl-2-phenyl-4-ethoxyoxazole)benzofuran compound
  • 2-Substituted-3-arylmethanone-6-(5-methyl-2-phenyl-4-ethoxyoxazole)benzofuran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of 4-(benzyloxy)-2-hydroxybenzaldehyde I ( Figure 4 ): Dissolve 2,4-dihydroxybenzaldehyde (100mg, 0.72mmol) in acetonitrile (15ml), then add potassium iodide (179.3mg, 1.08mmol) and sodium bicarbonate (90.7mg, 1.08mmol), then drop slowly Add benzyl chloride (100ul, 0.87mmol) and reflux for 12 hours. After the reaction was completed, it was quenched with water, extracted with ethyl acetate, the organic phases were combined, washed three times with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10 : 1) 110 mg of 4-(benzyloxy)-2-hydroxybenzaldehyde was obtained (colorless solid, yield 67%). 1 HNMR (CDCl 3 ; 300MHz), δ5.12(s, 2H, O CH 2 Ph) 6.40-6.64 (m, 2H, ArH), 7.41-7.43 (m, 6H, ArH), 9.73 (s, 1H, CHO), 11.44 (brs, 1H, OH).

Embodiment 2

[0047] (E)-5-(Benzyloxy)-2-(4-methoxystyryl)phenol II 1 Synthesis( Figure 4 ): under nitrogen atmosphere, add zinc powder (1.4g, 22mmol) in anhydrous tetrahydrofuran (20ml), then lower the temperature of the reaction system to -5~0°C, add titanium tetrachloride dropwise at this temperature (1.2ml, 11mmol), after the addition, the temperature of the reaction system was raised to room temperature, stirred for half an hour, and then refluxed for 2.5 hours. After the reflux, the temperature of the reaction system was lowered to -5~0°C again, and 4-(benzyloxy)-2-hydroxybenzaldehyde (1g, 4.4mmol) and p-methoxybenzaldehyde (721mg, 5.3mmol) of tetrahydrofuran solution, refluxed for 2 hours after dropping. After the reaction was completed, the reaction was quenched with 10% aqueous sodium bicarbonate solution, then extracted with dichloromethane, the organic phases were combined, washed three times with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced...

Embodiment 3

[0049] 6-(Benzyloxy)-2-(4-methoxyphenyl)benzofuran III 1 Synthesis( Figure 4 ): Dissolve (E)-5-(benzyloxy-2-(4-methoxystyryl)phenol (280mg, 0.84mmol) in tetrahydrofuran (15ml), add anhydrous potassium carbonate (695mg, 5.04 mmol), after stirring for 10 minutes, add iodine (1.28g, 5.04mmol), and stir at room temperature for 12 hours.After the reaction finished, quench the reaction with saturated aqueous sodium bicarbonate solution, then add dropwise saturated aqueous sodium bisulfite solution to remove The remaining iodine was extracted with ethyl acetate, the organic phases were combined, washed three times with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) 150 mg of 6-(benzyloxy)-2-methoxybenzofuran was obtained (yellow solid, yield 54%). 1 HNMR (CDCl 3 ;300MHz), δ3.87(s, 3H, OCH 3 ), 5.14(s, 2H, O CH 2 Ph), 6.826(s, 1H, ArH), 6.889-6.91...

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 relates to a 2-substituted-3-arylketone-6-(5-methyl-2-phenyl-4-ehtyoxyloxazole)benzofuran compound with the structural formula as shown in the specification. Compared with the prior art, the novel compound is prepared by introducing (5-methyl-2-phenyloxaole-4-yl)ethyoxyl to the 6 site of benzofuran by taking 3-ketone substituent benzofuran as the center of an aromatic ring; a preparation method of the compound is established and optimized; the prepared novel compound is subjected to an antibacterial screening experiment; the primary in-vitro antibacterial experiment confirms that the prepared novel compound has excellent broad-spectrum antibacterial activity and can be used for preparing novel antibacterial drugs.

Description

[0001] This application is a divisional application with the application number 201110292388.3, ​​the filing date is 2011.9.29, and the invention name is "3-methanone-6-substituted benzofuran compounds and their preparation methods and uses". technical field [0002] The present invention relates to compounds in the field of medicine and chemical industry and their preparation and application methods, in particular to a 2-substituted-3-aryl ketone-6-(5-methyl-2-phenyl-4-ethoxyoxane Azole) benzofuran compounds. Background technique [0003] In recent years, infections caused by a large number of drug-resistant strains have become a medical problem worldwide, and methicillin-resistant Staphylococcus aureus is one of the important categories. Since most antibacterial drugs used clinically have serious side effects, the development of safe and efficient antibacterial compounds has become an important research direction for medicinal chemists. [0004] Benzofuran derivatives are...

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): C07D413/12C07D413/14A61K31/423A61P31/04
CPCC07D413/12C07D413/14Y02A50/30
Inventor 傅磊姜发琴刘井宝刘晶晶刘文陆
Owner SHANGHAI JIAO TONG UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products