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Resveratrol dimer derivative and preparation and application methods thereof

A technology of resveratrol and dimer, applied in the field of medical engineering

Inactive Publication Date: 2011-09-14
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the design of resveratrol derivatives is varied, and the research on the activity of the prepared derivatives is also diverse, but the main research on resveratrol is still focused on anti-oxidation, anti-tumor, anti-diabetes and other aspects

Method used

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  • Resveratrol dimer derivative and preparation and application methods thereof
  • Resveratrol dimer derivative and preparation and application methods thereof
  • Resveratrol dimer derivative and preparation and application methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Preparation of 4-methyl o-iodoanisole:

[0080] Such as figure 1 As indicated, p-cresol (2 g, 18.5 mmol) was dissolved in methanol, and sodium iodide (2.77 g, 18.5 mmol) and sodium hydroxide (0.74 g, 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 tempera...

Embodiment 2

[0082] Preparation of methyl 3-iodo-5-methoxybenzoate:

[0083] Such as figure 2 As shown, with reference to Example 1, methyl p-hydroxybenzoate (5g, 32.8mmol) was iodized and methyl etherified to obtain methyl 3-iodo-5-methoxybenzoate (4.32g, 4.32g, 45%).

Embodiment 3

[0085] Preparation of 4-methoxyphenylacetylene:

[0086] Such as image 3 As indicated, 4-hydroxyiodobenzene (1 g, 4.5 mmol) was dissolved in acetone, potassium carbonate (1.245 g, 9 mmol) was added, and stirred. Under the protection of nitrogen, iodomethane (765mg, 5.4mmol) was added, after the dropwise completion, the temperature was raised to 68°C and refluxed. After reacting for 3 hours, evaporate acetone to dryness, extract with ethyl acetate, wash the organic phase with saturated brine, dry over anhydrous sodium sulfate, filter and evaporate to dryness to obtain a white solid, 4-methoxyiodobenzene (1.05g, 100%)

[0087] Dissolve 4-methoxyiodobenzene (1.05g, 4.5mmol) in triethylamine, add palladium chloride triphenylphosphine (63mg, 0.09mmol) and cuprous iodide (34mg, 0.18mmol), add under nitrogen Trimethylsilylacetylene (530 mg, 5.4 mmol), stirred overnight. After the reaction, triethylamine and excess trimethylsilylacetylene were distilled off to obtain a brown solid. ...

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Abstract

The invention discloses a resveratrol dimer derivative containing a Combretastin A-4 structure and preparation and application methods thereof, belonging to the technical field of medical engineering. By analyzing and researching reported anti-tumor activity and structure-activity relationship related to resveratrol and a derivative of the resveratrol, a series of derivatives with novel structures formed by polymerization of Combretastin A-4 and the resveratrol can be obtained through design and preparation. Through preliminary anti-tumor pharmacological tests, the prepared new compound is confirmed to have broad-spectrum tumor inhibitory activity to cancer cells.

Description

technical field [0001] The invention relates to a compound in the technical field of medical engineering and its preparation and application method, in particular to a resveratrol dimer derivative containing the structure of Combretastin A-4 and its preparation and application method. Background technique [0002] Combretastin A-4 (CA4) is a natural product isolated from plants. Petti and his colleagues isolated it from African dwarf trees in 1982, and found that it had a significant inhibitory effect on mouse P388 cells in the activity screen. Subsequent molecular biology research 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 h...

Claims

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Application Information

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