Metal organic gold (iii) complexes and their synthesis methods and applications

Abstract

The invention discloses a gold complex and a synthesis method and application thereof. The synthesis method of the gold complex comprises the following steps: placing chloroauric acid tetrahydrate orchloroaurate and a phenylethylamine ligand in an organic solvent for coordinating under a dark condition, cooling reactants, standing for crystallization, and collecting crystals to obtain the gold complex. The chloroaurate is sodium chloroaurate or potassium chloroaurate, and the phenylethylamine ligand is piperonyl amine. Applicants' experiments show that the complex has good proliferation inhibitory activity and drug resistance to certain tumor cell strains, and has low toxicity to human normal cell HL-7702 and high physiological stability. The structure of the complex is shown in the following formula (I).

Description

technical field

[0001] The invention relates to the technical field of medicine, in particular to a metal organic gold (III) complex and a synthesis method and application thereof. Background technique

[0002] Cisplatin and its analogs carboplatin and oxaliplatin have been successfully used to treat a variety of solid tumors, but serious drug resistance and side effects limit the clinical utility of these platinum drugs, so they have stronger anticancer activity and Metal complexes with lower side effects have become the research interest of many scholars. Some non-platinum metal complexes have shown high-efficiency and low-toxicity drug design properties, and some gold complexes also show anti-cancer mechanisms that are significantly different from platinum-based drugs. However, the low physiological stability of general gold complexes hinders Their therapeutic effects in the body.

[0003] 1,2,3,4-Tetrahydroisoquinoline (THIQ) is a special alkaloid compound that widely ...

Examples

Embodiment 1

[0021] Embodiment 1: the synthesis of target product Cyc-Au-1

[0022] Take KAuCl 4 (0.2mmol) and 3,4-dimethoxyphenethylamine (0.2mmol) are placed in the container, then add 30mL in the mixed solvent that is made up of dichloromethane and methanol (the volume ratio of dichloromethane and methanol is 1 : 1), the resulting mixture was refluxed and stirred for 24 hours under dark conditions, the resulting reactant was filtered, the filtrate was collected, and left to stand, yellow crystals were precipitated, the crystals were collected, and vacuum-dried to obtain a yellow solid product with a yield of 55%.

[0023] The product obtained in this embodiment is characterized:

[0024] 1) proton nuclear magnetic spectrum analysis, the obtained spectral data are as follows:

[0025] H NMR spectrum: 1 H NMR (400MHz, DMSO-d 6 )δ6.84(d,J=8.1Hz,1H),6.70(dd,J=8.1,1.6Hz,1H),3.74(s,3H),3.72(s,3H),2.81–2.67(t,J =5.4Hz 2H), 2.57(t, J=7.2Hz, 2H).

[0026] 2) Electrospray mass spectrometry ...

Embodiment 2

[0034] Embodiment 2: the synthesis of target product Cyc-Au-1

[0035] Example 1 was repeated except that the mixed solvent consisting of dichloromethane and methanol was replaced with chloroform. Yield 58%.

[0036] The product obtained in this example was analyzed by proton nuclear magnetic spectrum, electrospray mass spectrometry and X-ray single crystal diffraction, and it was determined that the product obtained in this example was the target product Cyc-Au-1.

Embodiment 3

[0037] Embodiment 3: the synthesis of target product Cyc-Au-1

[0038] Example 1 was repeated, except that the reaction was carried out at 25° C., and the reaction time was 48 hours. Yield 46%.

[0039] The product obtained in this example was analyzed by proton nuclear magnetic spectrum, electrospray mass spectrometry and X-ray single crystal diffraction, and it was determined that the product obtained in this example was the target product Cyc-Au-1.

technical field

[0001] The invention relates to the technical field of medicine, in particular to a metal organic gold (III) complex and a synthesis method and application thereof. Background technique

[0002] Cisplatin and its analogs carboplatin and oxaliplatin have been successfully used to treat a variety of solid tumors, but serious drug resistance and side effects limit the clinical utility of these platinum drugs, so they have stronger anticancer activity and Metal complexes with lower side effects have become the research interest of many scholars. Some non-platinum metal complexes have shown high-efficiency and low-toxicity drug design properties, and some gold complexes also show anti-cancer mechanisms that are significantly different from platinum-based drugs. However, the low physiological stability of general gold complexes hinders Their therapeutic effects in the body.

[0003] 1,2,3,4-Tetrahydroisoquinoline (THIQ) is a special alkaloid compound that widely ...

Examples

Embodiment 1

[0021] Embodiment 1: the synthesis of target product Cyc-Au-1

[0022] Take KAuCl 4 (0.2mmol) and 3,4-dimethoxyphenethylamine (0.2mmol) are placed in the container, then add 30mL in the mixed solvent that is made up of dichloromethane and methanol (the volume ratio of dichloromethane and methanol is 1 : 1), the resulting mixture was refluxed and stirred for 24 hours under dark conditions, the resulting reactant was filtered, the filtrate was collected, and left to stand, yellow crystals were precipitated, the crystals were collected, and vacuum-dried to obtain a yellow solid product with a yield of 55%.

[0023] The product obtained in this embodiment is characterized:

[0024] 1) proton nuclear magnetic spectrum analysis, the obtained spectral data are as follows:

[0025] H NMR spectrum: 1 H NMR (400MHz, DMSO-d 6 )δ6.84(d,J=8.1Hz,1H),6.70(dd,J=8.1,1.6Hz,1H),3.74(s,3H),3.72(s,3H),2.81–2.67(t,J =5.4Hz 2H), 2.57(t, J=7.2Hz, 2H).

[0026] 2) Electrospray mass spectrometry ...

Embodiment 2

[0034] Embodiment 2: the synthesis of target product Cyc-Au-1

[0035] Example 1 was repeated except that the mixed solvent consisting of dichloromethane and methanol was replaced with chloroform. Yield 58%.

[0036] The product obtained in this example was analyzed by proton nuclear magnetic spectrum, electrospray mass spectrometry and X-ray single crystal diffraction, and it was determined that the product obtained in this example was the target product Cyc-Au-1.

Embodiment 3

[0037] Embodiment 3: the synthesis of target product Cyc-Au-1

[0038] Example 1 was repeated, except that the reaction was carried out at 25° C., and the reaction time was 48 hours. Yield 46%.

[0039] The product obtained in this example was analyzed by proton nuclear magnetic spectrum, electrospray mass spectrometry and X-ray single crystal diffraction, and it was determined that the product obtained in this example was the target product Cyc-Au-1.

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