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Phthalocyanine zinc complex and its preparation method

A complex, zinc phthalocyanine technology, applied in the direction of organic chemistry, can solve the problems of reduced photodynamic activity, poor water solubility, unfavorable transportation, etc., to increase amphiphilicity and biocompatibility, low cost, improve photodynamic active effect

Inactive Publication Date: 2012-02-15
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The main factors affecting the photodynamic activity of photosensitizers are photophysical and chemical properties, amphiphilicity and cell uptake rate. The patent number is: "200410013492.4", and the name is "A new preparation method and application of amphiphilic phthalocyanine anticancer photosensitizer", the patent number is "200810070879.1", and the name is "A-(8-quinolineoxy) monosubstituted zinc phthalocyanine and its preparation "method" patents are all the results of long-term research by the inventor's research group, but the first patent is a tetra-substituted phthalocyanine, which is easy to aggregate and reduce its photodynamic activity; the second patent is extremely poor in water solubility, which is not conducive to Transport in the body

Method used

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  • Phthalocyanine zinc complex and its preparation method
  • Phthalocyanine zinc complex and its preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 1) Synthesis of 8-hydroxy-3,6-dioxahoctyl p-toluenesulfonate: 8g (0.2mol) sodium hydroxide, 18g (0.12mmo) l triethylene glycol and 19.07g (0.1mol) ) p-toluenesulfonyl chloride, reacted in water / tetrahydrofuran (60ml / 60ml) system at 15°C for 10 hours, evaporated the solvent after the reaction was completed, extracted the crude product with dichloromethane, and then extracted the crude product with ethyl acetate-dichloro Methane (1:4, v / v) was used as the eluent, and the product was separated by silica gel column chromatography to obtain 13g (42.71mmol) with a yield of 43%.

[0031] 2) Synthesis of 8-(4,6-dimethyl-2-pyrimidinyloxy)-3,6-dioxa-1-octanol: 10g (72.35mmol) anhydrous potassium carbonate, 3.09g (10mmol ) 8-hydroxy-3,6-dioxahoctyl p-toluenesulfonate and 1.78 g (14 mmol) 2-hydroxy-4,6-dimethylpyrimidine in N,N-dimethylformamide ( DMF, 15ml) was reacted at 60°C for 8 hours. After the reaction, the solvent was evaporated, and the crude product was extracted with...

Embodiment 2

[0035] Step 1): Sodium hydroxide, triethylene glycol and p-toluenesulfonyl chloride in a molar ratio of 1:1:1 were reacted in a water / tetrahydrofuran system at 0°C for 12 hours, and the solvent was distilled off after the reaction to obtain The crude product was extracted with dichloromethane, followed by silica gel column chromatography using ethyl acetate-dichloromethane as the eluent to obtain the 8-hydroxy-3,6-dioxaoctyl p-toluenesulfonate.

[0036]Step 2): The molar ratio of anhydrous potassium carbonate, 8-hydroxy-3,6-dioxahoctyl p-toluenesulfonate and 2-hydroxy-4,6-dimethylpyrimidine is 3:1:1, React in DMF at 25° C. for 12 hours. After the reaction, the solvent is evaporated, and the crude product is extracted with chloroform, followed by using methanol-chloroform as eluent, and using silica gel column chromatography to obtain the 8-( 4,6-Dimethyl-2-pyrimidinyloxy)-3,6-dioxa-1-octanol.

[0037] Step 3): Anhydrous potassium carbonate, 8-(4,6-dimethyl-2-pyrimidinyloxy)-3...

Embodiment 3

[0042] Step 1): Sodium hydroxide, triethylene glycol and p-toluenesulfonyl chloride in a molar ratio of 2:1:1 were reacted in a water / tetrahydrofuran system at 25°C for 6 hours, and the solvent was distilled off after the reaction to obtain The crude product was extracted with dichloromethane, followed by silica gel column chromatography using ethyl acetate-dichloromethane as the eluent to obtain the 8-hydroxy-3,6-dioxaoctyl p-toluenesulfonate.

[0043] Step 2): The molar ratio of anhydrous potassium carbonate, 8-hydroxy-3,6-dioxahoctyl p-toluenesulfonate and 2-hydroxy-4,6-dimethylpyrimidine is 10:2:1, React in DMF at 60° C. for 6 hours. After the reaction, the solvent is distilled off, and the crude product is extracted with chloroform, followed by methanol-chloroform as eluent, and separated by silica gel column chromatography to obtain the 8-( 4,6-Dimethyl-2-pyrimidinyloxy)-3,6-dioxa-1-octanol.

[0044] Step 3): Anhydrous potassium carbonate, 8-(4,6-dimethyl-2-pyrimidinylo...

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Abstract

The invention relates to a phthalocyanine zinc complex and a preparation method, the complex is (8-(4,6-dimethyl-2-pyrimidineoxy)-3,6-dioxane-1-octyloxy)phthalocyanine zinc, the molecular formula is C44H34N10O4Zn. According to the invention, pyrimidineoxy with alcoxyl long chain is introduced at the periphery of the macrolide of phthalocyanine zinc to increase the amphipathicity and biocompatibility and enhance the photodynamic activity, and the phthalocyanine zinc complex is difficult to aggregate such that cell ingestion rate is increased, and the photodynamic activity is enhanced; the complex has the advantages of single structure, no isomer existence and easy purification of the product; the synthetic method has the merits of simple process, less side reaction, high yield, easy raw material acquisition and low cost, and is in favor of industrial production.

Description

technical field [0001] The invention belongs to the field of synthesis of organic and metal coordination compounds, specifically zinc phthalocyanine complexes and preparation methods thereof, more specifically α / β-(8-(4,6-dimethyl-2-pyrimidinyloxy )-3,6-dioxa-1-octyloxy)zinc phthalocyanine and its preparation method. Background technique [0002] Phthalocyanine is a class of macrocyclic compounds with good photophysical and photochemical properties. It is used in high-tech fields, including semiconductor devices, photovoltaics and solar cells, electrophotography, rectifiers, LB films, low-dimensional conductor materials, gas sensors, Electrocatalysis, deodorants, bactericides, photosensitizers for photodynamic therapy, etc., among which photosensitizers have great development prospects. [0003] Factors affecting the photodynamic activity of photosensitizers mainly include photophysical and chemical properties, amphiphilicity and cell uptake rate. Its application" patent,...

Claims

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Application Information

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IPC IPC(8): C07D487/22
Inventor 刘见永薛金萍孟鲁波
Owner FUZHOU UNIV