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3-ketone-6-substituted-benzofuran compound as well as preparation method and application thereof

A technology of benzofuran and compound, applied in the field of 3-methanone-6-substituted-benzofuran compound and its preparation, can solve problems such as toxic and side effects, and achieve the effect of excellent antibacterial activity

Inactive Publication Date: 2014-12-10
SHANGHAI JIAOTONG UNIV
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  • 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

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  • 3-ketone-6-substituted-benzofuran compound as well as preparation method and application thereof
  • 3-ketone-6-substituted-benzofuran compound as well as preparation method and application thereof
  • 3-ketone-6-substituted-benzofuran compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of 4-(benzyloxy)-2-hydroxybenzaldehyde I ( Figure 4 ): Dissolve 2,4-dihydroxybenzaldehyde (100 mg, 0.72 mmol) in acetonitrile (15 ml), then add potassium iodide (179.3 mg, 1.08 mmol) and sodium bicarbonate (90.7 mg, 1.08 mmol), then Benzyl chloride (100 ul, 0.87 mmol) was slowly added dropwise and refluxed for 12 hours. After the reaction was completed, it was quenched with water, extracted with ethyl acetate, combined organic phases, washed three times with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by silica gel chromatography (petroleum ether: ethyl acetate=10 : 1) Obtain 110 mg of 4-(benzyloxy)-2-hydroxybenzaldehyde (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 (1.4 g, 22 mmol) into anhydrous tetrahydrofuran (20 ml), then lower the temperature of the reaction system to -5~0°C, add tetrachloride dropwise at this temperature Titanium oxide (1.2 ml, 11 mmol), 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 reflux, the temperature of the reaction system was lowered to -5~0°C again, and 4-(benzyloxy)-2-hydroxybenzaldehyde (1 g, 4.4 mmol) and p-methoxybenzaldehyde (721 mg, 5.3 mmol) in tetrahydrofuran, reflux 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 reduc...

Embodiment 3

[0049] 6-(Benzyloxy)-2-(4-methoxyphenyl)benzofuran III 1 Synthesis( Figure 4 ): Dissolve (E)-5-(benzyloxy-2-(4-methoxystyryl)phenol (280 mg, 0.84 mmol) in tetrahydrofuran (15 ml), add anhydrous potassium carbonate (695 mg, 5.04 mmol), after stirring for 10 minutes, add iodine (1.28 g, 5.04 mmol), and stir at room temperature for 12 hours. After the reaction, quench the reaction with saturated aqueous sodium bicarbonate solution, then add saturated sodium bisulfite dropwise Remove residual iodine from the aqueous solution, then extract with ethyl acetate, combine the organic phases, wash three times with saturated brine, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and purify through silica gel chromatography (petroleum ether: ethyl acetate=5 : 1), to obtain 150 mg of 6-(benzyloxy)-2-methoxybenzofuran (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), 6.889-6.918(d, 1H, ArH, J=8...

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Abstract

The invention relates to a 3-ketone-6-substituted-benzofuran compound as well as a preparation method and application thereof. The 3-ketone-6-substituted-benzofuran compound has the following structural formula: the preferable 3-ketone-6-substituted-benzofuran compound can be used for preparing medicament capable of inhibiting the biological activity of the microorganism. Compared with the prior art, the 3-ketone-6-substituted-benzofuran compound takes 3-ketone substituent group benzofuran as a aromatic ring center; (5-methyl-2-phenyloxazole-4-yl) ethyoxyl is introduced into the 6th position of the benzofuran to obtain a novel compound; the preparation method of the compound is built and optimized; the prepared novel compound is subjected to a bacteriostat screening experiment; a primary in-vitro bacteriostat experiment confirms that the parts of prepared new compounds have excellent broad spectrum bacteriostasis activity; and the 3-ketone-6-substituted-benzofuran compound can be used for preparing the novel antibacterial medicament.

Description

technical field [0001] The invention relates to a compound in the field of medicine and chemical industry and its preparation and application method, in particular to a 3-methanone-6-substituted-benzofuran compound and its preparation method 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, anti-inflammatory and so on. A large number of studies have found that the introduction of a ketone chain substituent at the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/12C07D413/14A61K31/423A61P31/04
CPCY02A50/30
Inventor 傅磊刘井宝姜发琴蒋玺臻刘晶晶刘文陆
Owner SHANGHAI JIAOTONG UNIV
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