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Benzofuran-3-ketone substitute phenyl compound as well as preparation method and application

A technology for benzofuran and compounds, applied in the field of benzofuran-3-methanone-substituted phenyl compounds and their preparation and application

Inactive Publication Date: 2012-10-03
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, compared with the positive control erythromycin, there is still a certain gap

Method used

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  • Benzofuran-3-ketone substitute phenyl compound as well as preparation method and application
  • Benzofuran-3-ketone substitute phenyl compound as well as preparation method and application
  • Benzofuran-3-ketone substitute phenyl compound as well as preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of 4-methyl o-iodoanisole:

[0022] Such as figure 1 As indicated, p-cresol (2 g, 18.5 mmol) was dissolved in methanol, NaI (2.77 g, 18.5 mmol), and NaOH (740 mg, 18.5 mmol) were added. The suspension was cooled to 0° C., 30 ml of 5% sodium hypochlorite solution was added dropwise to the suspension, and reacted for 5 hours. After the reaction was completed, the reaction was quenched with sodium thiosulfate, extracted with ether, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and evaporated to dryness to obtain a light yellow solid, which was separated on a silica gel column to obtain a light yellow oily liquid (740 mg, 17%), the oily liquid (740mg, 3.16mmol) was further selected to be dissolved in acetone, potassium carbonate (874mg, 6.32mmol) was added, and stirred. Under the protection of nitrogen, iodomethane (672mg, 4.74mmol) was added, after the dropwise completion, the temperature was raised to 68°C a...

Embodiment 2

[0024] Preparation of 5-methyl-2-(4-methoxyphenyl)-benzofuran:

[0025] 4-Methyl o-iodoanisole (783mg, 3.16mmol), palladium triphenylphosphine chloride (44mg, 0.06mmol) and cuprous iodide (24mg, 0.13mmol) were dissolved in anhydrous N,N-dimethyl Triethylamine (640mg, 6.32mmol) was added to methyl formamide under nitrogen, and after stirring for 15 minutes, p-methoxyphenylacetylene (835mg, 6.32mmol) was added and heated to 60°C. After reacting for 12 hours, add water to quench the reaction, extract with ethyl acetate, wash the organic phase with water and saturated brine, dry over anhydrous sodium sulfate, filter and evaporate to dryness to obtain a dark brown solid, which is separated on a silica gel column to obtain a white solid 2, 4 '-Dimethoxy-5-methyl-tolan (601 mg, 75.4%);

[0026] Dissolve 2,4'-dimethoxy-5-methyl-toluene (601mg, 2.3mmol) in methanol, add potassium carbonate (795mg, 5.75mmol), heat to 68°C, and reflux overnight. Cool to room temperature, evaporate meth...

Embodiment 3

[0028] Preparation of 4-acetoxybenzoic acid:

[0029] Dissolve 4-hydroxybenzoic acid (1 g, 7.24 mmol) in 20 ml of pyridine, add dropwise acetic anhydride (1.47 g, 14.4 mmol), react at room temperature for 1 hour, evaporate pyridine and acetic acid, extract with ethyl acetate, and use Wash with saturated sodium bicarbonate solution and saturated brine, dry over anhydrous sodium sulfate, evaporate the solvent to give 4-acetoxybenzoic acid (1.3g, 100%)

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Abstract

The invention belongs to the technical field of medicaments, relating to benzofuran-3-ketone substitute phenyl compound as well as preparation method and application. The compound is prepared by preparing 5- methyl-2-(4- methoxy phenyl)-benzofuran by using 4-O-methyl iodide anisole and than reacting with 4-micristin. The compound prepared by the invention can be used for inhibiting the bioactivity of cancer cells and microbes.

Description

technical field [0001] The invention relates to a compound in the field of pharmaceutical chemical technology and its preparation and application method, in particular to a benzofuran-3-methanone-substituted phenyl compound and its preparation and application. Background technique [0002] Combretastin A-4 (CA4) is a natural product isolated from plants. Petti and his colleagues isolated it from the African dwarf tree in 1982, and found that it had a significant inhibitory effect on mouse P38 cells in the activity screen. [0003] Subsequent molecular biology studies clarified that CA4 has a similar structure to colchicine and podophyllotoxin, and they all interact with the α subunit of tubulin to inactivate tubulin. Generally speaking, CA4 can hinder the formation of the spindle during cell division, so that the chromosomes cannot migrate to the spindles at both ends, so that the cells cannot divide normally and are inhibited in the Go phase. However, CA4 has poor water s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/80A61K31/343A61P35/00A61P31/00A61P31/04
Inventor 傅磊蒋玺臻刘文陆姜发琴谢东升张伟
Owner SHANGHAI JIAOTONG UNIV
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