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Structure, preparation and application of triethylene tetramine cantharidimide dimer derivative

A technology of cantharidin derivatives and crystals, which is applied to the structural field of unsaturated desmethyl cantharidinimide dimers, and can solve problems such as difficulty in 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 and application of triethylene tetramine cantharidimide dimer derivative
  • Structure, preparation and application of triethylene tetramine cantharidimide dimer derivative
  • Structure, preparation and application of triethylene tetramine cantharidimide dimer derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Dissolve 0.33g of unsaturated demethylcantharidin in 30ml of acetonitrile, add 0.15g of triethylenetetramine at a material ratio of 2:1, and stir at room temperature for 20 hours to 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 0.27g 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'-(3,6-diazaoctane-1,8-diyl)bis(3a,4,7,7a-tetrahydro-4,7-epoxy-1,3-dihydro isoindole-1,3-dione) 1 HNMR spectrum.

[0032] attached figure 2 is 2,2'-(3,6-diazaoctane-1,8-diyl)bis(3a,4,7,7a-tetrahydro-4,7-epoxy-1,3-dihydro isoindole-1,3-dione) 13 CNMR spectrum.

[0033] attached image 3 is 2,2'-(3,6-diazaoctane-1,8-diyl)bis(3a,4,7,7a-tetrahydro-4,7-epoxy-1,3-dihydro Isoindole-1,3-dione) crystal structure diagram, 30% ellipsoidal probability.

[0034] attached Figure 4 is 2,2'-(3,6-diazaoctane-1,8-diyl...

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Abstract

The invention provides a structure, preparation and application of a triethylene tetramine cantharidimide dimer derivative, and relates to a structure, preparation / crystallization method and partial property of cantharidin derivatives. The compound is a colorless rod-like crystal, has a melting point of 146.9-147.1 DEG C, a molecular formula of C22H26N4O6 and a chemical name of 2,2'-(3,6-diaza-1,8-octanediyl)bis(3a,4,7,7a-tetrahydro-4,7-epoxy-1,3-bishydroisoindole-1,3-dione), and has a structure as shown in the specification. The crystal belongs to the monoclinic crystal system and P21 space group, wherein a is 5.234(4)., b is 6.563(5)., c is 30.52(2)., alpha equaling to gamma is 90 degrees, beta is 92.618(12) degrees, V is 1047.2(13).<3>, and Z is 2. The compound is simple in preparation method, and has mild inhibition effects on lung cancer cells, breast cancer cells and colon 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 unsaturated demethylcantharimid dimers linked by triethylenetetramine groups. 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, ...

Claims

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Application Information

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IPC IPC(8): C07D519/00A61P35/00
CPCC07D519/00
Inventor 邢殿香石艳谭学杰刘耘
Owner QILU UNIV OF TECH
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