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Structure, preparation method and use of diethylenetriamine-based cantharidimide dimer derivative

A technology of cantharidin derivatives and crystals, which is applied in the field of unsaturated demethylcantharimid dimer structure, and can solve problems such as difficult crystallization

Inactive Publication Date: 2016-05-25
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No crystal structure of cantharimid dimer has been reported so far, indicating that its crystallization is difficult, which is a challenge

Method used

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  • Structure, preparation method and use of diethylenetriamine-based cantharidimide dimer derivative
  • Structure, preparation method and use of diethylenetriamine-based cantharidimide dimer derivative
  • Structure, preparation method and use of diethylenetriamine-based cantharidimide dimer derivative

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Experimental program
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Effect test

Embodiment 1

[0027] Dissolve 0.33g of unsaturated demethylcantharidin in 30ml of acetonitrile, add 0.10g of diethylenetriamine at a material ratio of 2:1, stir at room temperature for 20h, and obtain a white powdery precipitate. After the solvent evaporates to about 10ml remaining, After filtration, the resulting precipitate was recrystallized with methanol to obtain colorless rod-shaped crystals, which was the target product.

Embodiment 2

[0029] Dissolve 0.33g of unsaturated demethylcantharimid in 30ml of acetonitrile, add 0.23g of bis(2-bromoethyl)amine at a ratio of 2:1, stir at room temperature for 20h, and obtain a white powdery precipitate. The solvent was evaporated to about 10ml remaining, filtered, and the obtained precipitate was recrystallized with methanol to obtain colorless rod-shaped crystals, which was the target product.

[0030] Description of drawings.

[0031] attached figure 1 is 2,2'-(3-azopentane-1,5-diyl)bis(3a,4,7,7a-tetrahydro-4,7-epoxy-1,3-dihydroisoindole -1,3-diketone) of 1 HNMR spectrum.

[0032] attached figure 2 is 2,2'-(3-azopentane-1,5-diyl)bis(3a,4,7,7a-tetrahydro-4,7-epoxy-1,3-dihydroisoindole -1,3-diketone) of 13 CNMR spectrum.

[0033] attached image 3 is 2,2'-(3-azopentane-1,5-diyl)bis(3a,4,7,7a-tetrahydro-4,7-epoxy-1,3-dihydroisoindole -1,3-dione) crystal structure, ellipsoidal probability 30%.

[0034] attached Figure 4 is 2,2'-(3-azopentane-1,5-diyl)bis(3a,...

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Abstract

The invention relates to a structure, a preparation / crystallization method and partial characters of a cantharidin derivative. The compound is of a colorless rod crystal in appearance, the melting point is 126.0-127.2 DEG C, the molecular formula is C20H21N3O6, the chemical name is 2,2'-(3-azapentane-1,5-diyl)bi(3a,4,7,7a-tetrahydro-4,7-epoxy-1,3-dihydro-isoindole-1,3-dione), and the structure formula is shown in the specification. The structure is of a triclinic system, the space group is P-1, a is equal to 8.765(3) angstroms, b is equal to 9.709(3) angstroms, c is equal to 11.940(4) angstroms, alpha is equal to 76.723(4) degrees, beta is equal to 78.423(4) degrees, gamma is equal to 74.682(4) degrees, V is equal to 943.1(5) cubic angstroms, and Z is equal to 2. The preparation method of the compound is simple, and the compound has a mild inhibition effect on lung carcinoma cells and breast cancer cells.

Description

technical field [0001] The invention relates to the fields of organic chemistry, medicinal chemistry and crystallography, in particular to the structure, preparation and application of diethylenetriamine-linked unsaturated demethylcantharimid dimers. . Background technique [0002] As a typical small molecule protein phosphatase (proteinphosphatase, PP) inhibitor, since 1264, cantharidin has been used as an anticancer drug worldwide, it is effective for liver cancer, pancreatic cancer, colon cancer, oral cancer, Bladder cancer, breast cancer, lung cancer, and digestive tract tumors all have certain therapeutic effects. Remarkably, cancer cells that have become resistant to conventional drugs can still be killed by cantharidin, making the compound a new hope for treating cancer. It is not difficult to understand that while cantharidin can kill cancer cells, it is also toxic to some normal cells, especially normal cells in the gastrointestinal tract, urinary tract, and kidne...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00A61P35/00
CPCC07B2200/13C07D519/00
Inventor 谭学杰李坤邢殿香刘耘
Owner QILU UNIV OF TECH
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