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Synthesis method of colchicine

A technology for colchicine and synthetic methods, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of modification and improvement, low yield of colchicine, etc., achieve simple operation, improve biological activity and Toxic and side effects, the effect of being easy to industrialized production

Active Publication Date: 2017-10-24
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Description
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Problems solved by technology

For this reason, people hope to carry out modification research to colchicine, to improve its biological activity and toxic and side effects, however, the productive rate of existing colchicine is low, is not enough to its modification improvement, therefore, urgently needs to find a kind of It will be a very urgent and meaningful research topic to prepare colchicine by chemical synthesis in order to improve its biological activity and side effects through structural modification

Method used

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  • Synthesis method of colchicine
  • Synthesis method of colchicine
  • Synthesis method of colchicine

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preparation example Construction

[0029] Such as figure 1 Shown, the synthetic method of the colchicine of one embodiment, comprises the following steps (wherein, Me represented herein is a methyl group, and what NHAc represents is NHCOCH 3 ):

[0030] Step S110: under anhydrous conditions, the structural formula is The compound A and p-toluenesulfonamide are dissolved in the first organic solvent, and then copper sulfate is added to react at 100-160° C. to obtain the first reaction solution.

[0031] Wherein, the molar ratio of compound A to p-toluenesulfonamide is 1:1˜1:1.5.

[0032] Wherein, the first organic solvent is tetrahydrofuran or diethyl ether; preferably tetrahydrofuran, using tetrahydrofuran as the first organic solvent has a higher yield.

[0033] Wherein, copper sulfate is an oxidizing agent and a dehydrating agent in step S110, therefore, using copper sulfate in step S110 can effectively reduce preparation steps and improve efficiency. Specifically, the copper sulfate added in step S110 i...

Embodiment 1

[0079] The preparation process of the colchicine of the present embodiment is as follows:

[0080] (1) Dry anhydrous copper sulfate at 100°C for 8 hours to obtain dry anhydrous copper sulfate; then, under nitrogen conditions, dissolve compound A (25.5mmol) and p-toluenesulfonamide (30.6mmol) in To the tetrahydrofuran (100 mL) solution, dry anhydrous copper sulfate (51.0 mmol) was then added, and reacted at 120° C. for 24 hours, and cooled to room temperature to obtain a first reaction solution. In the first reaction solution, add pentamethylcyclopentadiene rhodium dichloride dimer (0.26mmol), silver hexafluoroantimonate (1.04mmol), sodium acetate (51mmol) and compound B (51.0mmol), And reacted at 80°C for 24 hours, the obtained reaction solution was filtered with diatomaceous earth, the filtrate was distilled under reduced pressure to remove tetrahydrofuran, the crude product was dissolved in ethyl acetate, and then washed with water, saturated sodium chloride, anhydrous sodiu...

Embodiment 2

[0105] The preparation process of the colchicine of the present embodiment is as follows:

[0106] (1) Dry anhydrous copper sulfate at 100°C for 12 hours to obtain dry anhydrous copper sulfate; then, under nitrogen conditions, dissolve compound A (25.5mmol) and p-toluenesulfonamide (25.5mmol) in Then add dry anhydrous copper sulfate (127.5 mmol) to the ether (100 mL) solution, react at 100° C. for 24 hours, and cool to room temperature to obtain the first reaction solution. In the first reaction solution, add pentamethylcyclopentadiene rhodium dichloride dimer (0.255mmol), silver hexafluoroantimonate (1.02mmol), sodium acetate (12.75mmol) and compound B (25.5mmol) , and reacted at 120°C for 12 hours, the obtained reaction solution was filtered with diatomaceous earth, the filtrate was distilled under reduced pressure to remove tetrahydrofuran, the crude product was dissolved in ethyl acetate, and then washed with water, saturated sodium chloride in sequence, anhydrous sulfuric...

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Abstract

The invention relates to a synthesis method of colchicine. According to the synthesis method of the colchicine, a compound as shown in the specification is used as a raw material, and then efficient intramolecular [5+2] cycloaddition is considered as key reaction; in combination with locating group guided dehydrogenation Hike reaction and Walker reaction, a molecular skeleton structure is rapidly constructed, so that an obtained structural formula, which has the same structure as a natural product, is the colchicine; and a modification research can be carried out on the colchicine favorably, so as to improve the bioactivity and the toxic and side effects of the colchicine.

Description

technical field [0001] The invention relates to a method for synthesizing colchicine. Background technique [0002] Since its isolation, colchicine has attracted the interest of many organic chemists with its novel chemical structure, and has attracted the attention of biologists because of its unique biological activity. Colchicine has many good biological activities, and there are still biologists conducting pharmacological research on it. In terms of gout treatment, colchicine is a specific prescription drug approved by the U.S. Food and Drug Administration (FDA) for the treatment of acute gout, and it has a good effect on relieving the symptoms of gout. [0003] Although colchicine is effective in the treatment of diseases such as gout and familial Mediterranean fever, due to the high toxicity of natural colchicine to normal tissues, patients often experience nausea, vomiting, diarrhea, and abdominal pain even when taking the drug under the guidance of a doctor In seve...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C233/32
Inventor 陈波胡亚剑刘鑫李闯创
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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