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Highly active oxoaporphinoid-rhodium (III) complex, and synthetic methods and application thereof

A synthetic method, compound technology, applied in the field of medicine

Inactive Publication Date: 2016-05-11
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Up to now, the research on metal complexes with oxidized aporphine alkaloids (such as Liriodendine, Papaverine oxide) as ligands at home and abroad is limited to the research group of the inventor.

Method used

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  • Highly active oxoaporphinoid-rhodium (III) complex, and synthetic methods and application thereof
  • Highly active oxoaporphinoid-rhodium (III) complex, and synthetic methods and application thereof
  • Highly active oxoaporphinoid-rhodium (III) complex, and synthetic methods and application thereof

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Experimental program
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Effect test

Embodiment 1

[0039] Embodiment 1: Synthesis of OGC-Rh(III) complex 1 by high-pressure solvothermal method

[0040] Weigh 0.1mmol OGC and add it to a 25cm Pyrex thick-walled glass tube with one end closed, add 2.0mL CH 3 CH 2 OH and 1.0mLCH 2 Cl 2 , and then weighed 0.1mmol of RhCl 3 ·nH 2 O was added to the glass tube, and after freezing with liquid nitrogen, the open end was melted and sealed under vacuum conditions. After mixing evenly, it was placed in an oven at 80°C. After 72 hours, red blocky crystals were formed in the glass tube (yield: 56%). The product was determined to be complex 1, namely [RhCl 3 (OGC)·CH 3 CH 2 OH], its crystal structure is as figure 1 shown.

Embodiment 2

[0041] Embodiment 2: Synthesis of OGC-Rh (III) complex 1 with normal pressure solution method

[0042] Weigh 0.28mmolRhCl 3 ·nH 2 O and 0.28mmol OGC dissolved in 10mL CH 2 Cl 2 and 10mLCH 3 CH 2 In the polar solvent composed of OH, the solution gradually changed from yellow to reddish brown; the reaction was stopped after reflux reaction at 60°C for 8 hours, and it was lowered to room temperature and left to stand overnight; filtered, the filtrate slowly evaporated at room temperature, and after two weeks, dark red square crystals It was separated out and collected after filtration (Yield: 70%). The product was determined to be complex 1 through infrared spectroscopy, ultraviolet spectroscopy, elemental analysis and electrospray mass spectrometry. 3 (OGC)·CH 3 CH 2 OH].

Embodiment 3

[0043] Embodiment 3: Synthesis of OGC-Rh (III) complex 1 with normal pressure solution method

[0044] Weigh 0.28mmolRhCl 3 ·nH 2 O and 0.28mmol OGC dissolved in 20mL CH 3 CH 2 In OH, reflux at 80°C for 2 hours to stop the reaction, drop to room temperature and let stand overnight; filter, the filtrate slowly evaporates at room temperature, dark red square crystals precipitate after two weeks, collect after filtration (Yield: 60%), The product was determined to be complex 1, namely [RhCl 3 (OGC)·CH 3 CH 2 OH].

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Abstract

The invention discloses a highly active oxoaporphinoid-rhodium (III) complex, and synthetic methods and an application thereof. The complex can be synthesized through adopting three different methods. The three synthetic methods gradually become simple from complex, and are completely different from present synthetic methods of oxoaporphinoid-metal complxes. The inhibition effect of a ligand OGC, an oxoglaucine-rhodium (III) complex and the complex disclosed in the invention on various tumor cell strains and in vivo tumor inhibition of the complex disclosed in the invention are investigated in the invention, and results show that complex disclosed in the invention has substantially enhanced in vitro and in vivo antitumor activity, and has far higher antitumor activity than the ligand OGC and the oxoglaucine-rhodium (III) complex. The structural formula of the highly active oxoaporphinoid-rhodium (III) complex is represented by formula (I) shown in the description.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a highly active oxidized aporphine-rhodium (III) complex and its synthesis method and application. Background technique [0002] Oxidized aporphine alkaloids are a class of alkaloids that exist in natural medicinal plants and have extensive and significant pharmacological activities. It is generally believed that the planar hyperdelocalized conjugated structure of most oxidized aporphine bases and the different substituent groups (such as methylenedioxy group (-O-CH 2 -O-), Methoxy (-OCH 3 )) has a significant relationship with its antitumor activity. If the reasonable structural modification can be carried out, it will have a good medicinal prospect. [0003] Oxoglaucine (OGC) is a typical oxidized aporphine, which is widely found in traditional Chinese medicine plants such as Magnoliaceae, Anemonaceae, Papaveraceae, and Fangjiaceae. The current research on papaverine mainl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCC07F15/008
Inventor 梁宏陈振锋刘延成韦健华覃其品吉晓辉莫祖煜
Owner GUANGXI NORMAL UNIV
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