A kind of synthetic method of cytochalasin compound flavipesine A

A technology for the synthesis of cytochalasin and its synthesis method, which is applied in the field of synthesis of the cytochalasin compound flavipesineA, which can solve the problems of high cost, long cycle, and expensive price, and achieve the effects of low cost, short production cycle, and high production efficiency

Active Publication Date: 2022-05-31
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the currently reported synthesis methods of cytochalasin generally have disadvantages such as many steps, low yield, high toxicity of reagents, and high price, which are not enough to meet the needs of its modification and improvement.
[0005] At present, no feasible chemical synthesis method for cytochalasin-like skeleton compounds has been reported, and the existing bio-fermentation extraction methods have disadvantages such as high cost, low yield, long cycle, difficult separation of products, and low purity.
The separation method reported in the literature can basically only obtain milligram-level products from dozens or even hundreds of grams of crude extract, and the efficiency of biological fermentation methods is low.

Method used

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  • A kind of synthetic method of cytochalasin compound flavipesine A
  • A kind of synthetic method of cytochalasin compound flavipesine A
  • A kind of synthetic method of cytochalasin compound flavipesine A

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Embodiment 1

[0032] Embodiment 1 of the present invention provides the synthetic method of compound B used in the present invention, which is as follows:

[0033]

[0034] P-toluenesulfonic acid (2.27 mmol) and 2,2,6,6-tetramethylpiperidine oxide (2.34 mmol) were mixed in 15 mL of dichloromethane solution under ice bath, and continued stirring (400 rpm) for 10 min under ice bath Then, the dichloromethane solution of this mixture was added to a 7 mL dichloromethane solution of compound D (0.38 mmol), and the stirring was continued (400 rpm) for 1 h under an ice bath, and then the reaction was quenched with 10 mL of saturated aqueous sodium bicarbonate solution under an ice bath. (10 min), extracted with ethyl acetate at room temperature, washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered under reduced pressure (500 mbar), and concentrated under reduced pressure (150 mbar), the obtained crude product was used in a silica gel column layer ...

Embodiment 2

[0040] A method for synthesizing a cytochalasin compound flavipesine A, the specific synthesis route of which is as follows:

[0041]

[0042] Specific steps are as follows:

[0043] (1) Compound B (0.075 mmol) was dissolved in 1.5 mL of anhydrous tetrahydrofuran at room temperature, zinc powder (0.90 mmol) and ammonium acetate (1.05 mmol) were added, and then stirred at 40° C. (450 rpm) for 2 h, and then At room temperature, filtered through celite (500 mbar) and concentrated under reduced pressure (150 mbar) to obtain the crude product, which was purified by silica gel column chromatography (eluent: V ethyl acetate: V petroleum ether=50:50) to obtain intermediate C (26.9 mg, 89% yield);

[0044] (2) At room temperature, dissolve intermediate C (0.05 mmol) in 1 mL of anhydrous tetrahydrofuran, add scandium trifluoromethanesulfonate (0.25 mmol), stir (450 rpm) for 2 h, and then use 1 mL of saturated sodium bicarbonate at room temperature The reaction was quenched with aqu...

Embodiment 3

[0046]

[0047] (1) Compound B (0.075 mmol) was dissolved in 0.15 mL of anhydrous tetrahydrofuran at room temperature, zinc powder (0.75 mmol) and ammonium acetate (0.90 mmol) were added, and then stirred at 40° C. (450 rpm) for 2 h, and then Filtered through celite (500 mbar) at room temperature and concentrated under reduced pressure (150 mbar) to obtain the crude product, which was purified by silica gel column chromatography (V ethyl acetate: V petroleum ether = 50:50) to give Intermediate C (22 mg, yield 73%);

[0048] (2) At room temperature, dissolve intermediate C (0.05 mmol) in 0.1 mL of anhydrous tetrahydrofuran, add scandium trifluoromethanesulfonate (0.20 mmol), stir (450 rpm) for 2 h, and then add 1 mL of saturated hydrogen carbonate at room temperature The reaction was quenched with aqueous sodium solution (10 min), extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered under reduced ...

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Abstract

The invention discloses a synthesis method of flavipesine A, a cytochalasin compound. The structural formula of the compound is: the synthesis method comprises: 1) dissolving compound B in tetrahydrofuran, adding a reducing agent at room temperature, and reacting at 40°C to obtain Intermediate C; 2) At room temperature, add the reaction reagent to the THF solution of Intermediate C to obtain Compound A. The reagents used in the synthesis process provided by the present invention can be purchased commercially at low prices, and this reaction strategy is also applicable to the synthesis of other types of cytochalasin-like intermediate product derivatives, so as to study the structure modification and structure-activity relationship of this type of alkaloids , New drug development and mass production lay the foundation.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing a cytochalasin compound flavipesine A. Background technique [0002] Natural products with complex and diverse structures have always been an important source of small molecule drug discovery. Although natural products have rich and diverse structures, their natural sources are often very limited, and it is difficult to conduct in-depth research on their chemical properties and biological activities. Therefore, how to be concise and efficient. , Obtaining a large number of natural products with specific structures and their analogs has become an important research content of natural product chemical synthesis, biosynthesis and organic synthesis methodology. [0003] Cytochalasan is a kind of fungal polyamino acid hybrid secondary metabolite with significant biological functions. So far, more than 400 different compounds in this family have be...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107
CPCC07D491/107Y02P20/55
Inventor 邓军吴海丁一鸣龙先文曲春雷
Owner NANKAI UNIV
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