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

Benzofuran compounds and their preparation and use

A technology of benzofuran and compound, applied in the field of benzofuran compound and preparation thereof, can solve problems such as toxic and side effects

Inactive Publication Date: 2017-06-13
SHANGHAI JIAOTONG UNIV
View PDF1 Cites 3 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
  • Benzofuran compounds and their preparation and use
  • Benzofuran compounds and their preparation and use
  • Benzofuran compounds and their preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Synthesis of 4-(benzyloxy)-2-hydroxybenzaldehyde I ( figure 1 ): 2,4-dihydroxybenzaldehyde (5.00g, 36mmol) was dissolved in acetonitrile (500mL), then potassium iodide (9.00g, 54mmol) and sodium bicarbonate (4.50g, 54mmol) were added, after adding, slowly Benzyl chloride (5.50 g, 43.5 mmol) was added dropwise and refluxed for 12 h. 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) 5.25 g of 4-(benzyloxy)-2-hydroxybenzaldehyde was obtained (white solid, yield 64%).

[0056] 1 H NMR (CDCl 3 ;300MHz), δ5.11(s, 2H, OCH 2 Ph)6.51-6.52(d, 1H, ArH), 6.60-6.63(dd, 1H, ArH), 7.36-7.46(m, 6H, ArH), 9.72(s, 1H, OH), 11.48(s, 1H, OH).

Embodiment 2

[0058] Synthesis of triphenylbenzylphosphine chloride: Benzyl chloride (2.88g, 31.6mmol) and triphenylphosphine (8.57g, 32.7mmo) were dissolved in 20mL of acetonitrile and heated to reflux overnight. After the reaction was completed, it was cooled to room temperature and filtered to obtain 7.5 g of triphenylbenzylphosphine chloride (white solid, yield 61%).

[0059] 1 H NMR (DMSO; 300MHz), δ5.25-5.30(d, 2H, J=15.9Hz, CH 2 P), 6.98-7.01 (m, 2H, ArH), 7.19-7.29 (m, 3H, ArH), 7.65-7.77 (m, 12H, Ph), 7.87-7.93 (m, 3H, Ph).

Embodiment 3

[0061] Synthesis of 4-benzyloxybenzyl alcohol: 4-hydroxybenzyl alcohol (10.00g, 80.55mmol) was dissolved in 150mL of acetonitrile, then potassium carbonate (22.27g, 161.1mmol) was added, and benzyl chloride (12.24 g, 96.66mmol), reflux 12h. After the reaction was completed, quenched with water, extracted with ethyl acetate, combined organic phases, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by silica gel column chromatography (petroleum ether: ethyl acetate = 3:1 ) to obtain 15 g of 4-benzyloxybenzyl alcohol (white solid, yield 87%).

[0062] 1 H NMR (DMSO; 300MHz), δ4.39-4.41 (d, 2H, CH 2 OH), 5.00-5.04(t, 1H, CH 2 OH), 5.06(s, 2H, OCH 2 Ph), 6.94-6.97 (d, 2H, ArH), 7.20-7.23 (d, 2H, ArH), 7.31-7.45 (m, 5H, ArH).

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 benzofuran compound as well as a preparation method and application thereof. The structural formula of the benzofuran compound is as shown in formula (I) in the specification, wherein R1, R2 and R4 are respectively selected from hydrogen, C1-C5 alkyl, nitryl, halogen, ester group, hydroxyl, amino, acylamino or alkoxyl; R3 represents hydrogen, C1-C5 alkyl, benzyl, aryl or heteroaryl. The invention also relates to the application of the benzofuran compound in inhibition on gram-positive bacterium. According to the preparation method disclosed by the invention, an aromatic ring of a 3-ketoxime substituent benzofuran structure is taken as the center to build and optimize the compound; the prepared novel compound is subjected to an antibacterial screening experiment, and a primary antibacterial test proves that the prepared compound has broad-spectrum antibacterial activity.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and specifically relates to a benzofuran compound and its preparation and application. Background technique [0002] 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. [0003] Benzofuran derivatives are an important class of heterocyclic compounds, which have a very wide range of biological effects, such as antibacterial, antitumor, and anti-inflammatory. A large number of studies have found that the introduction of a ketone chain substituent at the 3-position of the benzofuran ring has an important impact on the antibacterial activ...

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): C07D307/81C07D307/80A61K31/343A61P31/04
CPCC07D307/80C07D307/81Y02A50/30
Inventor 傅磊姜发琴徐步哲包健何宛张勇
Owner SHANGHAI JIAOTONG 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