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Platinum (II) metal complex for specifically inhibiting proliferation of lung carcinoma cell, and synthesis method and application thereof

A synthesis method and compound technology, applied in the field of medicine, can solve the problems of destroying the planarity and independence of the oxidized isoaporphine parent ring, affecting the anti-tumor activity and advantages of the complex, and affecting the active site of the electron cloud density, etc. The effect of good medicinal value

Active Publication Date: 2017-03-15
GUANGXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the research on the antitumor activity of this type of metal complexes, no antitumor metal complexes with specific proliferation inhibitory effect on lung cancer cells (such as the typical non-small cell lung cancer tumor line NCI-H460) have been found.
The applicant believes that among the oxidized isoaporphine-metal complexes we have reported, it is characterized by 1-N and 11-C bidentate chelation coordination on the parent ring of the oxidized isoaporphine ligand Coordination with metal ions (such as platinum(II)) in a certain way destroys the planarity and independence of the oxidized isoaporphantyl ring, thereby affecting its electron cloud density and possible active sites, and then May affect the antitumor activity and advantages of the complex

Method used

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  • Platinum (II) metal complex for specifically inhibiting proliferation of lung carcinoma cell, and synthesis method and application thereof
  • Platinum (II) metal complex for specifically inhibiting proliferation of lung carcinoma cell, and synthesis method and application thereof
  • Platinum (II) metal complex for specifically inhibiting proliferation of lung carcinoma cell, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Synthesis of Ligand L, i.e. 9-(3-chloropropanamide)-oxidized isoaporphine

[0039] Ligand L was synthesized according to the following synthetic route:

[0040]

[0041] The specific synthesis method is:

[0042] 1) Preparation of 9-(3-chloropropanamido)-oxidized isoaporphine with reference to existing literature (Tang, H.; etal. Eur. J. Med. Chem., 2009, 44: 2523-2532.) , the detailed steps are as follows:

[0043] 1.1) Dissolve 15.0g (about 0.1mol) of phthalic anhydride and 12.0g (about 0.1mol) of β-phenylethylamine in 100mL of ethanol, reflux for 5 hours, filter while hot, cool to room temperature, precipitate crystals, pump Filtered to obtain white flaky crystal compound a with a yield of 75%. Mix and heat 75g (0.56mol) of anhydrous aluminum trichloride and 15g of sodium chloride to 140°C for melting, slowly add 53g (0.2mol) of compound a to it, after the addition is completed, heat up to 180°C, and stir for 2 hours , introduced into the grinder by...

Embodiment 2

[0061] Embodiment 2: the synthesis of ligand L

[0062] 1) with embodiment 1;

[0063] 2) Weigh 1mmol of 9-(3-chloropropanamide)-oxyisoapophine and 0.8mmol of 2-(2-aminoethyl)pyridine, use ethanol as solvent, the amount of ethanol is 10mL, after dissolving The mixed solution was obtained and reacted at 37°C for 72 hours. The obtained reactant was suction filtered, washed with ether, dried, and then purified by silica gel column chromatography (chloroform / methanol=100:1→10:1, volume ratio) to obtain a yellow solid Product (65% yield).

[0064] The obtained product was analyzed by infrared spectrum, high-resolution mass spectrometry, proton nuclear magnetic resonance spectrum, carbon nuclear magnetic resonance spectrum, etc., and determined to be the target product ligand L.

Embodiment 3

[0065] Embodiment 3: the synthesis of ligand L

[0066] 1) with embodiment 1;

[0067] 1) Weigh 1mmol of 9-(3-chloropropanamide)-oxidized isoaporphine and 10mmol of 2-(2-aminoethyl)pyridine, use methanol as solvent, the amount of methanol is about 100mL, after dissolving The mixed solution was obtained and reacted at 90°C for 6 hours. The obtained reactant was suction filtered, washed with ether, dried, and then purified by silica gel column chromatography (chloroform / methanol=50:1→15:1, volume ratio) to obtain a yellow solid Product (80% yield).

[0068] The obtained product was analyzed by infrared spectrum, high-resolution mass spectrometry, proton nuclear magnetic resonance spectrum, carbon nuclear magnetic resonance spectrum, etc., and determined to be the target product ligand L.

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Abstract

The invention discloses a platinum (II) metal complex for specifically inhibiting proliferation of a lung carcinoma cell, and a synthesis method and an application thereof. The structural formula of the platinum (II) metal complex for specifically inhibiting the proliferation of the lung carcinoma cell is as shown in formula (I). The synthesis method of the platinum (II) metal complex for specifically inhibiting the proliferation of the lung carcinoma cell includes: fetching a compound as shown in following formula (II) and dichlorodi(dimethyl sulfoxide)platinate(II), dissolving the compound and the dichlorodi(dimethyl sulfoxide)platinate(II) in polar solvent, reacting under a heating or non-heating condition, and then obtaining reaction liquid containing the target product. The metal complex can specifically inhibit the proliferation of the lung carcinoma cell NCI-H460, and IC50 (half maximal inhibitory concentration) value is up to 5.01+ / -0.54 microns, and the metal complex embodies good potential pharmaceutical value, and is hopefully used in preparation of specific lung cancer resisting pharmaceuticals. The formula (I) and the formula (II) show structures as follows.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a platinum (II) metal complex for specifically inhibiting the proliferation of lung cancer cells and its synthesis method and application. Background technique [0002] Lung cancer is one of the most common causes of death in cancer, accounting for 1 / 3 of cancer mortality. At present, 80% of clinically common lung cancer is non-small cell lung cancer (NSCLC), and 70% of NSCLC patients are diagnosed at an advanced stage, so it is difficult to perform radical treatment by means of surgery or radiotherapy (Yang, J.J.; et al. Oncology Progress, 2010, 8:538-545.). There is an urgent need for researchers to design and develop one or a series of new anti-tumor drugs with high activity or high selectivity for lung cancer cells. Judging from the existing research results, the discovery and derivation of new anti-lung cancer chemotherapy drugs from the active ingredients of natural prod...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCC07F15/0093
Inventor 陈振锋梁宏刘延成韦祖壮覃其品张运良韩红华陈婷余砚成邝文彬
Owner GUANGXI NORMAL UNIV
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