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Zinc phthalocyanine derivative and preparation method thereof

A derivative, zinc phthalocyanine technology, applied in the field of organic and metal coordination compound synthesis, can solve the problems of reducing photodynamic activity, poor water solubility, unfavorable transportation, etc., to increase amphiphilicity and biocompatibility, and low cost , enhance the effect of photodynamic activity

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

AI Technical Summary

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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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 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%.

[0026] 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 ch...

Embodiment 2

[0031] The specific process of step 1) includes: the molar ratio of sodium hydroxide, triethylene glycol and p-toluenesulfonyl chloride is 1:2:1, react in the water / tetrahydrofuran system at 0°C for 12 hours, after the reaction Evaporate the solvent, extract the crude product with dichloromethane, then use ethyl acetate-dichloromethane as the eluent, and use silica gel column chromatography to obtain 8-hydroxy-3,6-dioxoctyl-p-toluenesulfonic acid Ester, the yield is 40%.

[0032] The specific process of step 2) includes: anhydrous potassium carbonate, 8-hydroxyl-3,6-dioxahoctyl p-toluenesulfonate and 2-hydroxyl-4,6-dimethylpyrimidine in a molar ratio of 10 : 1:1, react in DMF at 25°C for 12 hours, evaporate the solvent after the reaction, extract the crude product with chloroform, then use methanol-chloroform as eluent, and use silica gel column chromatography to obtain 8-(4,6-Dimethyl-2-pyrimidinyloxy)-3,6-dioxa-1-octanol, 60% yield.

[0033] The specific process of step 3)...

Embodiment 3

[0039] The specific process of step 1) includes: the molar ratio of sodium hydroxide, triethylene glycol and p-toluenesulfonyl chloride is 2:1:1, react in the water / tetrahydrofuran system at 25°C for 6 hours, after the reaction Evaporate the solvent, extract the crude product with dichloromethane, then use ethyl acetate-dichloromethane as the eluent, and use silica gel column chromatography to obtain 8-hydroxy-3,6-dioxoctyl-p-toluenesulfonic acid Esters, the yield is 50%.

[0040] The specific process of step 2) includes: anhydrous potassium carbonate, 8-hydroxyl-3,6-dioxahoctyl p-toluenesulfonate and 2-hydroxyl-4,6-dimethylpyrimidine in a molar ratio of 3 : 2:1, react in DMF at 60°C for 6 hours, evaporate the solvent after the reaction, extract the crude product with chloroform, then use methanol-chloroform as eluent, and use silica gel column chromatography to obtain 8-(4,6-Dimethyl-2-pyrimidinyloxy)-3,6-dioxa-1-octanol, 80% yield.

[0041] The specific process of step 3) ...

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PUM

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Abstract

The invention relates to a zinc phthalocyanine derivative and a preparation method thereof. The chemical formula of the derivative is C56H52N12O8Zn. In the method, a pyrimidine oxy group with a long alcoxyl chain is introduced at the periphery of a large ring of zinc phthalocyanine, so that the amphipathy and the biocompatibility of the zinc phthalocyanine are improved, and the photodynamic activity is improved. The zinc phthalocyanine derivative is difficult to gather, so the improvement on the cellular uptake rate is facilitated, and the photodynamic activity is improved; the derivative has a single compound structure, an isomer does not exist, and the product can be purified easily; and the synthetic method is simpler, higher in yield and low in cost, and is favorable for industrialized production, few side reactions are performed, and raw materials are readily available.

Description

technical field [0001] The invention belongs to the field of synthesis of organic and metal coordination compounds, in particular to a zinc phthalocyanine derivative and a preparation method thereof, more specifically to a bis-(8-(4,6-dimethyl-2-pyrimidine oxide) base)-3,6-dioxa-1-octyloxy)zinc phthalocyanine. 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, the pa...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61K31/506
Inventor 刘见永薛金萍孟鲁波
Owner FUZHOU UNIV
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