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A kind of polyamine phthalocyanine and its derivatives, their preparation and application

A technology of phthalocyanine derivatives and derivatives, which can be used in medical preparations containing active ingredients, drug combinations, organic chemistry, etc., and can solve the problems of lack of phthalocyanine derivatives and low degree of aggregation.

Inactive Publication Date: 2016-09-14
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, phthalocyanine derivatives that can satisfy both good antitumor activity, good solubility and low aggregation degree are still extremely lacking.

Method used

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  • A kind of polyamine phthalocyanine and its derivatives, their preparation and application
  • A kind of polyamine phthalocyanine and its derivatives, their preparation and application
  • A kind of polyamine phthalocyanine and its derivatives, their preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Polyamine phthalocyanine R1 and preparation method thereof, represented by reaction formula as figure 2 shown.

[0076] (1) Under the protection of nitrogen, the dichloromethane solution of triphenylchloromethane is slowly added dropwise into the dichloromethane solution of ethylenediamine with a constant pressure titration funnel, the molar ratio of triphenylchloromethane and ethylenediamine 1:3, titrated for about 4 hours, then stirred at room temperature for 4 hours to obtain intermediate 10;

[0077] (2) Add intermediate 10 and p-hydroxybenzaldehyde to the ethanol solution at a molar ratio of 1:1.1, add 1.5 equivalents of sodium borohydride after reacting for 3 hours, and continue stirring for 3 hours to obtain intermediate 12;

[0078] (3) Under nitrogen protection, intermediate 12, basic catalyst and 4-nitrophthalonitrile were added to DMF at a molar ratio of 1:2:1.2, and reacted at 40°C for 4 hours to obtain intermediate 13;

[0079] (4) Under the protection of...

Embodiment 2

[0081] Polyamine phthalocyanine R2 and preparation method thereof, represented by reaction formula as figure 2 shown.

[0082] (1) Under the protection of nitrogen, the dichloromethane solution of triphenylchloromethane is slowly added dropwise into the dichloromethane solution of ethylenediamine with a constant pressure titration funnel, the molar ratio of triphenylchloromethane and ethylenediamine 1:3, titrated for about 4 hours, then stirred at room temperature for 4 hours to obtain intermediate 10;

[0083] (2) Add intermediate 10 and p-hydroxybenzaldehyde to the ethanol solution at a molar ratio of 1:1.1, add 1.5 equivalents of sodium borohydride after reacting for 3 hours, and continue stirring for 3 hours to obtain intermediate 12;

[0084] (3) Under nitrogen protection, intermediate 12, basic catalyst and 4-nitrophthalonitrile were added to DMF at a molar ratio of 1:2:1.2, and reacted at 40°C for 4 hours to obtain intermediate 13;

[0085] (4) Under the protection of...

Embodiment 3

[0088] Polyamine phthalocyanine R3 and its preparation, represented by the reaction formula as image 3 shown.

[0089](1) Diethylethylenediamine 10' and p-hydroxybenzaldehyde were added to the ethanol solution at a molar ratio of 1:1.1, and 1.5 equivalents of sodium borohydride was added after the reaction for 3 hours, and the stirring reaction was continued for 3 hours to obtain the intermediate 12';

[0090] (2) Under nitrogen protection, intermediate 12', basic catalyst and 4-nitrophthalonitrile were added to DMF at a molar ratio of 1:2:1.2, and reacted at 40°C for 4 hours to obtain intermediate 13' ;

[0091] (3) Under the protection of nitrogen, intermediate 13', metal salt, and DBU are added in n-amyl alcohol in a molar ratio of 1:1:1, and the polyamine phthalocyanine R3 is refluxed for 24 hours;

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Abstract

The invention discloses polyamine phthalocyanine and a derivative thereof. The structural general formula of the derivative of polyamine phthalocyanine is shown in descriptions. The derivative of polyamine phthalocyanine, disclosed by the invention, has relatively good solubility and photosensitive activity, has a certain targeting function and is suitable for serving as a photosensitizer for PDT (Photodynamic Therapy). The invention further relates to preparation methods and application of polyamine phthalocyanine and the derivative thereof.

Description

technical field [0001] The invention relates to a phthalocyanine and its preparation and application, in particular to a polyamine phthalocyanine and its derivatives, as well as their preparation and application. Background technique [0002] Photodynamic therapy (PDT) is a new type of therapy developed in recent years based on photodynamic response to treat precancerous lesions and malignant tumors and other diseases. The earliest research on PDT in this century can be traced back to 1960, when R.L. Lipson and S. Schwartz injected crude hematoporphyrin into the patient's body to make the tumor lesion tissue fluorescent visualized during the operation. Different from traditional chemotherapy, radiotherapy and surgery, PDT realizes the damage and death of tumor lesion tissue and cells through the comprehensive action of three non-toxic elements: light, photosensitizer and oxygen. Compared with the current traditional therapy, PDT not only has unique advantages such as high s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCA61K41/0071C07D487/22
Inventor 魏少华王傲周林卢珊周家宏林云
Owner NANJING NORMAL UNIVERSITY
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