6-Hydroxyloxoisoaporphine rare earth complexes, and synthetic method and application thereof

A rare earth complex, hydroxyl oxidation technology, applied in the field of medicine, to achieve significant in vitro anti-tumor activity, good medicinal value.

Inactive Publication Date: 2013-12-18
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] On the other hand, studies have shown that 6-hydroxyisoaporphine alkaloids have good antitumor activity, but it is still blank to use it as an antitumor active ligand to study metal complexes.

Method used

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  • 6-Hydroxyloxoisoaporphine rare earth complexes, and synthetic method and application thereof
  • 6-Hydroxyloxoisoaporphine rare earth complexes, and synthetic method and application thereof
  • 6-Hydroxyloxoisoaporphine rare earth complexes, and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Weigh 6-hydroxyisoapomorphine and Tb(NO 3 ) 3 ·6H 2 O, 1 mmol each, 6-hydroxyisoaporphine was dissolved in 40 mL of 80% (v / v) methanol, Tb(NO 3 ) 3 ·6H 2 O was dissolved in 20mL of water, the two were mixed and reacted, reacted at 75°C for 24 hours, concentrated and evaporated to remove most of the solvent (80% of the total amount of solvent added), cooled to room temperature and stood still, and precipitated reddish-brown block crystals ( Yield 95%).

[0055] Identify the resulting red blocky crystals:

[0056] (1) Infrared spectrum, the spectrum is as follows figure 1 shown;

[0057] IR(KBr):3376,3082,2972,1620,1596,1563,1481,1418,1384,1311,1289,1245,1226,1149,1042,1026,987,860,791,757,721,589,525,463cm -1 .

[0058] (2) UV spectrum, such as figure 2 shown;

[0059] (3) Elemental analysis results, as shown in the following table 1;

[0060] Table 1:

[0061]

[0062] (4) Electrospray mass spectrometry, such as image 3 shown;

[0063] ESI-MS m / z:807...

Embodiment 2

[0068] Weigh 6-hydroxyisoapomorphine and Dy(NO 3 ) 3 ·6H 2 O, 1 mmol each, dissolve 6-hydroxyisoaporphine in 100 mL of 40% (v / v) ethanol, and Dy(NO 3 ) 3 ·6H 2 O was dissolved in 50mL of 30% (v / v) methanol, the two were mixed and reacted at 70°C for 4 hours, concentrated and evaporated to remove most of the solvent (80% of the total amount of solvent added), cooled to room temperature and allowed to stand , a reddish-brown product was precipitated (88% yield).

[0069] The resulting reddish-brown product was subjected to infrared spectrum, ultraviolet spectrum, elemental analysis, electrospray mass spectrometry combined with X-ray single crystal diffraction analysis, and the obtained spectra were as follows: Figure 5 , Figure 6 , Figure 7 and Figure 8 Shown, wherein the data of infrared spectroscopy, elemental analysis, electrospray mass spectrometry are as follows:

[0070] IR(KBr):3390,3087,1620,1597,1564,1482,1448,1418,1384,1311,1289,1245,1149,1042,987,860,791,...

Embodiment 3

[0076] Weigh 6-hydroxyisoapomorphine and Gd(NO 3 ) 3 ·6H 2 O, 1 mmol each, 6-hydroxyl isoaporphine was dissolved in 80 mL of a mixed solution of methanol and ethanol (volume ratio 1:1), and Gd(NO 3 ) 3 ·6H 2 O) Dissolve in 20mL of water and methanol (volume ratio 3:1) mixed solution, mix the two to react, react at 85°C for 42 hours, concentrate and evaporate to remove most of the solvent (85% of the total amount of solvent added) , cooled to room temperature and stood still, and a reddish-brown product was precipitated (yield 85%).

[0077] The resulting reddish-brown product was subjected to infrared spectrum, ultraviolet spectrum, elemental analysis, electrospray mass spectrometry combined with X-ray single crystal diffraction analysis, and the obtained spectra were as follows: Figure 9 , Figure 10 , Figure 11 and Figure 12 Shown, wherein the data of infrared spectroscopy, elemental analysis, electrospray mass spectrometry are as follows:

[0078] IR(KBr):3390,3...

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Abstract

The invention discloses a series of new 6-hydroxyloxoisoaporphine rare earth complexes, having a structural general formula as shown in specification, wherein Ln is La, Ce, Pr, Nd, Sm, Eu, Gd, Tb or Dy. The complexes are synthesized from 6-hydroxyloxoisoaporphine and the rare earth metal nitrates (Ln(NO3)3.xH2O as raw materials through a heating or reflux reaction. According to the complexes and the synthetic method and application thereof disclosed by the invention, the proliferation inhibition activity of the complexes to a plurality of human tumor cell strains such as SK-OV-3, SK-OV-3 / DDP and T-24 is investigated, and results indicate that all of the complexes have remarkable antitumor activity in vitro; in particular, the 6-hydroxyloxoisoaporphine lanthanum complex has extremely remarkable activity to cervical cancer cells SK-OV-3; in addition, apart from the 6-hydroxyloxoisoaporphine europium complex, the other complexes all have a good inhibition effect on human ovarian cancer / cis-platinum persisters SK-OV-3 / DDP.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a rare earth complex of 6-hydroxyloxidized isoaporphine and its synthesis method and application. Background technique [0002] Cancer and cardiovascular and cerebrovascular diseases have become two major diseases that seriously endanger human life and health. The development of new anticancer drugs and the study of their mechanism of action have always been a hot spot in the chemical research of anticancer drugs, which has extremely important practical significance. [0003] As a research hotspot in the new discipline of inorganic medicinal chemistry, the extensive preliminary research on inorganic complex drugs provides broad prospects for the development of such new metal-based anticancer agents. Platinum anticancer agents are the most commonly used inorganic anticancer drugs at present, and have quite good curative effects on various cancers. However, due to the high toxic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/00A61K31/555A61P35/00
Inventor 陈振锋梁宏刘延成覃其品张传辉
Owner GUANGXI NORMAL UNIV
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