Piperazine-modified phthalocyanine complex and preparation method thereof

A complex, piperazine technology, applied in the directions of medical preparations, pharmaceutical formulations, and drug combinations containing active ingredients, can solve the problems of difficult separation, many side reactions, and difficult synthesis.

Inactive Publication Date: 2014-05-07
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the existing substituted phthalocyanine metal complexes have problems such as difficult synthesis, many side reactions, and difficult separation.

Method used

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  • Piperazine-modified phthalocyanine complex and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Embodiment 1 (Ia, R=C 2 h 5 )

[0069] 1) Add compound 1 (3.45 g, 0.03 mol) and compound 2 (5.04 g, 0.03 mol) into 30ml of acetonitrile, after the two are dissolved, add K 2 CO 3 (20.70 g, 0.15 mol), reacted at 85 °C under nitrogen protection for 12 h; after the reaction was completed, spin dry acetonitrile, add 100 ml water, extract with 500 ml dichloromethane, collect the organic layer, spin dry, and then distilled Chloromethane:methanol=30:1 was used as the eluent, and compound 3 (5.41 g) was obtained by gel column separation with a yield of 90%. 1 H NMR (400 MHz, CDCl 3 ): δ 1.00-1.10 (m, 3 H, CH 3 ), 1.20-1.30 (m, 3 H, CH 3 ), 2.38-2.46 (m, 2 H, CH 2 ), 2.46-2.66 (br s, 8 H, CH 2 ), 3.18-3.22 (m, 2 H, CH 2 ), 4.12-4.20 (m, 2 H, CH 2 ). HRMS (ESI): m / z C 10 h 21 N 2 o 2 [M+H] + , the calculated value is 201.1598; the measured value is 201.1604.

[0070] 2) Lithium aluminum hydride (LiAlH 4 ) (0.21 g, 0.006 mol) was added to a round-bottomed flask ...

Embodiment 2

[0073] Example 2 (IIa, R=C 2 h 5 )

[0074] 1) Add compound 1 (3.45 g, 0.03 mol) and compound 2 (5.04 g, 0.03 mol) into 30 ml of acetonitrile, after the two are dissolved, add K 2 CO 3 (20.70 g, 0.15 mol), and reacted for 12 h at 85 °C under the protection of nitrogen; after the reaction was completed, spin dry acetonitrile, add 100 ml water, extract with 500 ml dichloromethane, collect the organic layer, spin dry, and then distilled Chloromethane:methanol=30:1 was used as the eluent, and compound 3 (5.41 g) was obtained by gel column separation with a yield of 90%. 1 H NMR (400 MHz, CDCl 3 ): δ 1.00-1.10 (m, 3 H, CH 3 ), 1.20-1.30 (m, 3 H, CH 3 ), 2.38-2.46 (m, 2 H, CH 2 ), 2.46-2.66 (br s, 8 H, CH 2 ), 3.18-3.22 (m, 2 H, CH 2 ), 4.12-4.20 (m, 2 H, CH 2 ). HRMS (ESI): m / z C 10 h 21 N 2 o 2 [M+H] + , the calculated value is 201.1598; the measured value is 201.1604.

[0075] 2) Lithium aluminum hydride (LiAlH 4 ) (0.21 g, 0.006 mol) was added to a round-bott...

Embodiment 3

[0078] Embodiment 3 (If, R=(CH 2 CH 2 O) 3 CH 3 )

[0079] 1) Compound HO(CH 2 CH 2 O) 3 CH 3 (16.41 g, 0.1 mol) and compound (22.80 g, 0.12 mol) was added to dichloromethane, and after both were dissolved, triethylamine (15.18 g, 0.15 mol) was added and reacted for 12 h at room temperature under the protection of nitrogen; after the reaction was completed, the crude product was extracted with water , collecting the organic layer, followed by petroleum ether-ethyl acetate as eluent, separated by silica gel column to obtain the compound TsO(CH 2 CH 2 O) 3 CH 3 (27.04 g). The yield is 85% 【1】 .

[0080] 2) Compound TsO(CH 2 CH 2 O) 3 CH 3 (3.19 g, 0.01 mol) and compound (1.31 g, 0.01 mol) was added into 20 ml of acetonitrile at a molar ratio of 1:1, and after both were dissolved, K 2 CO 3 (6.90 g, 0.05 mol), reacted at 85 °C under nitrogen protection for 8-12 h; after the reaction was completed, spin dry acetonitrile, add 100 ml water, extract the crude...

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Abstract

The invention discloses a piperazine-modified phthalocyanine complex as well as a preparation method and an application thereof. Piperazine molecules are introduced into the macrocyclic periphery of a metal phthalocyanine so as to enhance the amphipathy, the biocompatibility and the targeting of the phthalocyanine. A piperazine group contains two N atoms, so that after the synthesized phthalocyanine complex enters a tissue, if the tissue is normal, the single excitation state of the phthalocyanine can be quenched by lone pair electrons on the N atoms of the piperazine group under a light irradiation condition. Thus, the generation of singlet oxygen is avoided. If the tumor tissue is in a weak acid state, the N atoms are protonated, so that the single excitation state of the phthalocyanine cannot be quenched. Therefore, the singlet oxygen is generated so as to kill tumor cells. Based on the theory, the selectivity of the photodynamic therapy of the phthalocyanine is improved due to the introduction of the piperazine group, so that the damage of the phthalocyanine to the normal tissue is reduced. The piperazine-modified phthalocyanine complex has a single structure and does not contain isomers, and is easy to purify and low in cost, thereby being favorable for industrial production.

Description

technical field [0001] The invention belongs to the field of synthesis of organic and metal coordination compounds, and in particular relates to a class of piperazine-modified phthalocyanine complexes and a preparation method and application thereof. technical field [0002] The invention belongs to the field of synthesis of organic and metal coordination compounds, and in particular relates to a class of piperazine-modified phthalocyanine complexes and a preparation method and application thereof. Background technique [0003] Because phthalocyanine is relatively easy to synthesize and has high stability, phthalocyanine is widely used in industry. Recently, the application of phthalocyanine in high-tech fields has become an emerging hotspot, including semiconductor devices, photovoltaics and solar cells, xerography, rectifiers, LB films, low-dimensional conductor materials, gas sensors, electrocatalysis, deodorants, Bactericides, photosensitizers for photodynamic therapy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCA61K41/0071C07D487/22
Inventor 刘见永薛金萍袁晓
Owner FUZHOU UNIV
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