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Podophyllotoxin structure modified derivative and preparation method thereof

A technology for podophyllotoxin and epipodophyllotoxin is applied in the field of structure-modified derivatives of podophyllotoxin and the preparation thereof, which can solve the problems of difficult modification and modification of podophyllotoxin structure, and achieves good application value and potential, production and production. High efficiency and easy operation

Inactive Publication Date: 2021-09-17
GUANGDONG MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The main purpose of the present invention is to provide a structurally modified derivative of podophyllotoxin and its preparation method. The preparation method of the present invention has mild reaction conditions, easy operation, high product yield, high purity, high atom economy, and successful It solves the problem that the structure of podophyllotoxin is difficult to modify and transform in the prior art

Method used

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  • Podophyllotoxin structure modified derivative and preparation method thereof
  • Podophyllotoxin structure modified derivative and preparation method thereof
  • Podophyllotoxin structure modified derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033]

[0034] In acetonitrile, add the compounds of the above formulas (II), (III) and (IV), copper iodide (CuI), triethylamine, then raise the temperature to 25°C, and stir and seal the reaction at this temperature for 24h; wherein, The mol ratio of formula (II) compound and cuprous iodide (CuI) is 1:0.05, the mol ratio of formula (II) compound and triethylamine is 1:0.1, formula (II) compound and (III), (IV ) compound in a molar ratio of 1:1:1, and the ratio of the compound of formula (II) in millimoles (mmol) to acetonitrile in milliliters (ml) is 1:5.

[0035]After the reaction, the reaction system was naturally cooled to room temperature, concentrated by rotary evaporation to obtain a crude product, which was subjected to 300-400 mesh silica gel column chromatography, using ethyl acetate and petroleum ether mixture as eluent, wherein acetic acid The volume ratio of ethyl ester and sherwood oil is 1:5, thereby obtains the target product formula (I) compound (C) of whi...

Embodiment 2

[0040]

[0041] In acetonitrile, add the compounds of the above formulas (II), (III) and (IV), copper iodide (CuI), and triethylamine, then raise the temperature to 40°C, and stir and seal the reaction at this temperature for 12h; wherein, The molar ratio of formula (II) compound and cuprous iodide (CuI) is 1:0.2, the molar ratio of formula (II) compound and triethylamine is 1:0.2, formula (II) compound and (III), (IV ) compound in a molar ratio of 1:2:2, and the ratio of the compound of formula (II) in millimoles (mmol) to acetonitrile in milliliters (ml) is 1:8.

[0042] After the reaction, the reaction system was naturally cooled to room temperature, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was subjected to 200-300 mesh silica gel column chromatography, using a mixture of ethyl acetate and petroleum ether as the eluent, wherein The volume ratio of ethyl acetate and sherwood oil is 1:8, thereby obtains the targe...

Embodiment 3

[0047]

[0048] In acetonitrile, add the compounds of the above formulas (II), (III) and (IV), copper iodide (CuI), triethylamine, then raise the temperature to 30°C, and stir and seal the reaction at this temperature for 8h; wherein, The molar ratio of formula (II) compound and cuprous iodide (CuI) is 1:0.15, the molar ratio of formula (II) compound and triethylamine is 1:0.3, formula (II) compound and (III), (IV ) compound in a molar ratio of 1:1.5:1.5, and the ratio of the compound of formula (II) in millimoles (mmol) to acetonitrile in milliliters (ml) is 1:6.

[0049] After the reaction, the reaction system was naturally cooled to room temperature, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was subjected to 200-300 mesh silica gel column chromatography, using a mixture of ethyl acetate and petroleum ether as the eluent, wherein The volume ratio of ethyl acetate and sherwood oil is 1:6, thereby obtains the targe...

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Abstract

The invention discloses a podophyllotoxin structure modified derivative and a preparation method thereof, and belongs to the technical field of organic chemical synthesis. The derivative is an N-substituted-4[beta]-amino-4-deoxy epipodophyllotoxin derivative, the structural formula of the derivative is shown as a formula (I), and in the formula (I), R1 and R2 are independently selected from phenyl, 2-thienyl, alkyl-substituted aryl, halogen-substituted aryl, C1-C6 alkyl or camphor substituent. The preparation method of the podophyllotoxin structure modified derivative has the advantages of being mild in synthesis condition, easy to operate, high in product yield, high in atom economy and the like, has good scientific research value and application prospect, provides a brand new route for structural modification of the compound, can play an important role in the field of synthesis of drug intermediates, pesticide intermediates and the like, reduces the production cost, and has good application value and potential in industry and scientific research.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a structurally modified derivative of podophyllotoxin and a preparation method thereof. Background technique [0002] Podophyllotoxin (PPT) is an aryl naphthalene lignan lactone isolated from the plant Dysosma of the genus Podophyllum. most notably. However, podophyllotoxin has serious adverse reactions to the gastrointestinal tract and is not suitable for direct clinical use. Since the 1950s, researchers have carried out a lot of structural modification work on podophyllotoxin, and its derivatives etoposide (VP-16) and teniposide (teniposide, VM-26) have been successfully marketed and become As the first-line clinical anti-tumor drug, through unremitting efforts, some new PPT derivatives with better pharmacological and pharmacokinetic properties have been discovered, but there are still serious adverse reactions, such as prone to gastrointestinal disorders, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04
CPCC07D493/04C07B2200/07
Inventor 杨忠涛杨渭光周子彤何月玲罗辉
Owner GUANGDONG MEDICAL UNIV
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