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Synthesis method of cytochalasin compound and cytochalasin derivative

A technology for cytochalasin and a synthesis method, which is applied in the field of synthesis of cytochalasin compounds and cytochalasin derivatives, can solve the problems of high toxicity, high price and low yield of reagents, and achieves safe reagents and simple operation. , the effect of high yield

Active Publication Date: 2021-07-16
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the currently reported synthesis methods of cytochalasin generally have shortcomings such as many steps, low yield, high toxicity of reagents, and high price, which cannot meet the needs of its modification and improvement.

Method used

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  • Synthesis method of cytochalasin compound and cytochalasin derivative
  • Synthesis method of cytochalasin compound and cytochalasin derivative
  • Synthesis method of cytochalasin compound and cytochalasin derivative

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Embodiment 1

[0091] Embodiment 1 of the present invention discloses a preparation method of cytochalasin compound aspochalasin Z, comprising the following steps:

[0092]

[0093] (A) Dissolve 1.6mmol of compound A in 1.6L of anhydrous dichloromethane, then add 3.23mmol of 1,5,7-triazabicyclo[4.4.0]-5-decene and stir at room temperature for 14h, Then add saturated aqueous sodium bicarbonate solution to quench the reaction;

[0094] (B) Take the above-mentioned quenched reaction product and add ethyl acetate to extract, then wash with saturated aqueous sodium chloride solution, then add anhydrous sodium sulfate to dry, filter, concentrate under vacuum, and finally obtain after purification by silica gel column chromatography The cytochalasin compound aspochalasin Z (293 mg, yield 49%, theoretical yield).

[0095] The theoretical yield of the cytochalasin compound aspochalasin Z was calculated to be 593 mg; the actual yield was 293 mg when measured on the obtained product; the yield calc...

Embodiment 2

[0107] Embodiment 2 of the present invention discloses a preparation method of cytochalasin compound aspochalasin Z, comprising the following steps:

[0108] (A) Dissolve 1.6mmol of Compound A in 32mL of anhydrous dichloromethane, then add 3.21mmol of 1,5,7-triazabicyclo[4.4.0]-5-decene and stir at room temperature for 14h, then Add saturated aqueous sodium bicarbonate solution to quench the reaction;

[0109] (B) Take the above-mentioned quenched reaction product and add ethyl acetate to extract, then wash with saturated aqueous sodium chloride solution, then add anhydrous sodium sulfate to dry, filter, concentrate under vacuum, and finally obtain after purification by silica gel column chromatography The cytochalasin compound aspochalasin Z (223mg, yield rate 38%, theoretical yield 593mg).

[0110] The theoretical yield of the cytochalasin compound aspochalasin Z was calculated to be 593 mg; the actual yield was 223 mg when measured on the obtained product; the yield calcul...

Embodiment 3

[0121] Embodiment 3 of the present invention discloses a preparation method of cytochalasin compound aspochalasin Z, comprising the following steps:

[0122] (A) Dissolve 1.6mmol of compound A in 1.6L of anhydrous dichloromethane, then add 4.81mmol of 1,5,7-triazabicyclo[4.4.0]-5-decene and stir for 14h at room temperature. Then add saturated aqueous sodium bicarbonate solution to quench the reaction;

[0123] (B) Take the above-mentioned quenched reaction product and add ethyl acetate to extract, then wash with saturated aqueous sodium chloride solution, then add anhydrous sodium sulfate to dry, filter, concentrate under vacuum, and finally obtain after purification by silica gel column chromatography The cytochalasin compound aspochalasin Z (285 mg, yield 48%, theoretical yield 593 mg).

[0124] The theoretical yield of the cytochalasin compound aspochalasin Z was calculated to be 593 mg; the actual yield was 285 mg when measured on the obtained product; the yield calculate...

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Abstract

The invention discloses a preparation method of a cytochalasin compound aspochalasin Z. The whole steps are simple, the adopted reagent is safe, and the raw material cost is low. Meanwhile, the invention also discloses a method for synthesizing a cytochalasin derivative compound AA, a compound BB, a compound CC and a compound DD, a method for synthesizing a cytochalasin compound trichoderone A and a method for synthesizing a cytochalasin compound trichoderone by using the compound aspochalasin Z. The steps of each method are simple, the adopted raw materials and reagents are safe and low in price, the cytochalasin compound can be simply and efficiently prepared.

Description

technical field [0001] The present invention relates to the technical field of cytochalasin compounds, in particular to a synthesis method of cytochalasin compounds and cytochalasin derivatives. Background technique [0002] Cytochalasins are a class of fungal polyamino acid hybrid secondary metabolites with significant biological functions. Currently, more than 400 different cytochalasins have been successfully isolated and identified. Cytochalasin compounds have a wide range of biological activities, specifically including nematicide activity, antifouling and anti-inflammatory activity, inducing leukemia cell apoptosis, inhibiting angiogenesis, and anti-multidrug-resistant bacteria, and even some cells Relaxin also has anti-HIV and phytotoxic activity. In addition, cytochalasin compounds also have anti-tumor properties, and are expected to be used to prepare anti-cancer drugs. [0003] However, since the main target of cytochalasin is actin, the specific mechanism of act...

Claims

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Application Information

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IPC IPC(8): C07D209/96C07D491/107
CPCC07D209/96C07D491/107C07B2200/07
Inventor 邓军吴海丁一鸣龙先文曲春雷
Owner NANKAI UNIV
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