Norcantharidin esterified derivatives and preparation method thereof

A technology for cantharidin esters and derivatives, which is applied in the field of synthesis of norcantharidin esterified derivatives, can solve the problems of undisclosed secondary products and the like, and achieve the effects of rapid and accurate content and control of the reaction process.

Active Publication Date: 2009-11-11
山东世博金都药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Nor does it disclose any method of producing secondary products as a corollary

Method used

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  • Norcantharidin esterified derivatives and preparation method thereof
  • Norcantharidin esterified derivatives and preparation method thereof
  • Norcantharidin esterified derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Preparation of 7-oxabicyclo[2,2,1]heptane-2,3-dicarboxylic acid butyl ester

[0088]

[0089] C 16 H 26 O 5

[0090] 298.38

[0091] Add 2g norcantharidin into the reaction flask, then add 6ml excess n-butanol, then add H 2 SO 4 0.1ml mix. Place the reaction flask on a thermostatic magnetic stirrer, stir and heat to 80°C-100°C and reflux for 70 minutes. After the reaction was terminated, an oily liquid was obtained. The product was washed with cold water 3 times×20ml, and a white waxy solid was obtained by suction filtration. The white solid was dissolved by adding preheated n-hexane at 45°C, and crystallized in the refrigerator. The next day, suction filtration gave a white solid crystal 7 -Oxabicyclo[2,2,1]heptane-2,3-dicarboxylic acid butyl ester, weighing a total of 2.24g.

[0092] TLC identification

[0093] Developing agent: chloroform: acetone: formic acid = 97: 3: 2

[0094] TLC color development method: iodine cylinder smoked.

[0095] Tests have proved that usi...

Embodiment 2

[0099] Preparation of 7-oxabicyclo[2,2,1]heptane-2,3-dicarboxylic acid hexyl ester

[0100]

[0101] C 20 H 34 O 5

[0102] 354.49

[0103] Synthesis steps: add 7.5ml (0.06mol) excess n-hexanol to the reaction flask, add 3.36g (0.02mol) norcantharidin, and then add H 2 SO 40.12ml mix. Place the reaction flask on a thermostatic magnetic stirrer, stir and heat to 80°C and reflux for 65 min. After the reaction was terminated, an oily liquid was obtained. The product was washed with cold water 3 times×20ml, and a white waxy solid was obtained by suction filtration. The white solid was dissolved by adding preheated n-hexane at 45°C, and crystallized in the refrigerator. The next day, suction filtration gave a white solid crystal 7 -Oxabicyclo[2,2,1]heptane-2,3-dicarboxylic acid hexyl ester, weighing a total of 3.56g pure product.

[0104] TLC identification

[0105] Developing agent: chloroform: acetone: formic acid = 97: 3: 2; the rest are the same as in Example 1.

Embodiment 3

[0107] Synthesis of 7-oxabicyclo[2,2,1]heptane-2,3-dicarboxylic acid octyl ester

[0108] The reaction formula is:

[0109]

[0110] C 24 H 42 O 5

[0111] 410.59

[0112] Add 6ml excess n-octanol to the reaction flask, add 2g norcantharidin, and then add H 2 SO 4 0.06ml mix. Place the reaction flask on a thermostatic magnetic stirrer and stir and heat to 45°C, reflux for 5 hours and terminate the reaction to obtain an oily liquid. The product is washed 3 times with cold water × 20ml, filtered with suction to obtain a white waxy solid, and dissolved in preheated n-hexane at 45°C. The white solid was crystallized in the refrigerator, and filtered with suction after 1-24 hours to obtain 7-oxabicyclo[2,2,1]heptane-2,3-dicarboxylic acid octyl ester, and weighed to obtain 2.27g pure product.

[0113] TLC identification

[0114] Developing agent: chloroform: acetone: formic acid = 97: 3: 2

[0115] TLC color development method: iodine cylinder smoked.

[0116] Tests have proved that ...

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Abstract

The invention relates to norcantharidin esterified derivatives and a preparation method thereof. The norcantharidin esterified derivatives are 7-oxabicyclo[2,2,1] heptane-2 carboxylic acid butyl ester-3 carboxylic acid butyl ester, 7-oxabicyclo[2,2,1] heptane-2,3 dicarboxylic acid hexyl ester, 7-oxabicyclo[2,2,1] heptane-2,3 dicarboxylic acid monooctyl ester, 7-oxabicyclo[2,2,1] heptane-2,3 dicarboxylic acid decyl ester, and 7-oxabicyclo[2,2,1] heptane-2,3 dicarboxylic acid dodecyl ester. The preparation method comprises the following steps: adding a corresponding alcohol in a mixing amount, adding norcantharidin and sulfuric acid in a mixing amount, mixing, stirring and heating the mixture, refluxing the mixture at 45 to 100 DEG C for 60 to 300 minutes, and obtaining oily liquid after reactions are finished; and washing the products with cold water, filtering solution obtained to obtain white waxy solid, adding preheated normal hexane in the white waxy solid to dissolve the white waxy solid, freezing obtained solution at the temperature of between 18 DEG C below zero and 4 DEG C for refrigeration and crystallization for 1 to 24 hours, and filtering the solution to obtain crystals, namely the corresponding norcantharidin esterified derivatives.

Description

Technical field [0001] The invention belongs to the synthetic category of norcantharidin esterified derivatives, and specifically relates to norcantharidin esterified derivatives and a preparation method thereof. [0002] The invention also relates to the thin-layer chromatography (TLC) identification method of the novel norcantharidin esterified derivative and the ratio of the developing agent. Background technique [0003] Cantharidin is an anti-tumor active ingredient extracted from the traditional Chinese medicine cantharidin. Through the Diels-Alder reaction, furan and maleic anhydride are artificially synthesized norcantharidin. It was tested for primary liver cancer in the 1970s. The latest research found that Formazan has a certain inhibitory effect on a variety of tumor cells, but its application is limited due to its strong stimulating effect on the urinary system and digestive system. [0004] In recent years, more than 100 kinds of cantharidin derivatives have been sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08A61P35/00
Inventor 阎敬武邸春盛杜成德
Owner 山东世博金都药业有限公司
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