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A silicon phthalocyanine with an axial ester bond linking piperidine or morpholine derivatives

A morpholine derivative, silicon phthalocyanine technology, applied in the field of photodynamic drug or photosensitizer preparation, can solve the problems of limited clinical application, complex synthesis route, high skin phototoxicity, etc., and achieves improved tissue penetration ability and clear structure. , easy to prepare

Active Publication Date: 2017-07-04
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hematoporphyrin derivatives have shown certain curative effects, but also exposed serious disadvantages: the maximum absorption wavelength (380-420nm) is not in the red light region (650-800nm) with better transmittance to human tissue, and the skin has high phototoxicity. It is a mixture and its composition is unstable, so its clinical application is limited, so the development of a new generation of photodynamic drugs (photosensitizers) is an international research hotspot
However, the synthesis route of Pc4 is complicated, the preparation cost is high, and the stability is poor.

Method used

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  • A silicon phthalocyanine with an axial ester bond linking piperidine or morpholine derivatives
  • A silicon phthalocyanine with an axial ester bond linking piperidine or morpholine derivatives
  • A silicon phthalocyanine with an axial ester bond linking piperidine or morpholine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis and physicochemical properties of bis[3-(N-piperidine)propyl]silicon phthalocyanine (structure shown in the following formula):

[0038]

[0039] Under the protection of nitrogen, add dichlorosilicon phthalocyanine (244.7mg, 0.4mmol), 3-(N-piperidine) propionic acid 1.2-2.4mmol (preferably 2.0mmol) to toluene or xylene or dioxane 20 -50ml (preferably toluene, 30ml), reflux for 20-36 hours (preferably 24 hours). The solvent was removed by vacuum rotary evaporation, dissolved in 100ml of dichloromethane, centrifuged to remove insolubles, the dichloromethane solution was extracted with water (3×100ml), the organic layer was collected, and then extracted with dilute hydrochloric acid (0.1-0.5mmol), and the aqueous layer was collected. The water layer was neutralized with 1M sodium hydroxide, a blue precipitate was precipitated, centrifuged, washed with water, and dried in vacuum to obtain a blue product with a yield of 45%. The maximum absorption peak of the product...

Embodiment 2

[0042] Synthesis and physicochemical properties of bis[3-(N-methyl-N-piperidine)propyl] silicon phthalocyanine diiodide (structure shown in the following formula):

[0043]

[0044] Under the protection of nitrogen, add bis[3-(N-piperidine)propyl]silicon phthalocyanine (0.023mmol) and excess methyl iodide to chloroform (20ml), reflux for 1~4 hours (preferably 2 hours) Stir at room temperature for 16 to 48 hours (preferably 24 hours). After filtration, the filter cake was washed three times with 50 ml of chloroform, and dried under vacuum to obtain the product with a yield of 73%. The maximum absorption peak of the product in DMF is at 684nm, and the maximum absorption wavelength in aqueous solution is at 691-700nm.

[0045] The structural characterization data of the product are as follows: HR-MS (ESI) m / z: 441.1888 [M-2I] 2+ ; 1 H NMR(DMSO-d6, 400MHz, ppm): δ9.70~9.82 (m, 8H, Pc-H α ), δ8.55~8.66 (m, 8H, Pc-H β ), δ2.14~2.25 (m, 4H, 3-H), δ1.98~2.09 (m, 4H, 3-H), δ1.74~1.85 (s, 6...

Embodiment 3

[0047] Synthesis of bis[3-(N-morpholine)propyl]silicon phthalocyanine (structure shown in the following formula):

[0048]

[0049] Under the protection of nitrogen, add dichlorosilicon phthalocyanine (244.7mg, 0.4mmol), 3-(N-morpholine) propionic acid 1.2-2.4mmol (preferably 2.0mmol) to toluene or xylene or dioxane 20 -50ml (preferably toluene, 30ml), reflux for 20-36 hours (preferably 24 hours). The solvent was removed by vacuum rotary evaporation, dissolved in 100ml of dichloromethane, centrifuged to remove insolubles, the dichloromethane solution was extracted with water (3×100ml), the organic layer was collected, and then extracted with dilute hydrochloric acid (0.1-0.5mmol), and the aqueous layer was collected. The water layer was neutralized with 1M sodium hydroxide, and a blue precipitate was precipitated, centrifuged, washed with water, and dried in vacuum to obtain a blue product with a yield of 43%. The maximum absorption peak of the product in DMF is located at 681 n...

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Abstract

The invention discloses a silicon phthalocyanine axially bonded with a piperidine or morpholine derivative with an ester bond as well as a preparation method and application of the silicon phthalocyanine and belongs to the field of preparing photodynamic drugs or photosensitizers. The silicon phthalocyanine can be used as a photosensitizer used for carrying out photodynamic antibacterium, photodynamic cancer resistance, photodynamically treating other diseases, photodynamic disinfection and photodynamic diagnosis and has the advantages of simple preparation, strong photosensitization and the like, and the maximum absorption spectrum is located in a near infrared region.

Description

Technical field [0001] The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and particularly relates to a silicon phthalocyanine with piperidine or morpholine derivatives connected by axial ester bonds, and a preparation method and application thereof. Background technique [0002] Phthalocyanine complexes are an important class of functional materials, which can be developed into functional materials for different purposes through different structural modifications. By introducing suitable substituents and central ions on the phthalocyanine ring, it is possible to develop oxidation catalysts, desulfurization catalysts, nonlinear optical materials, photosensitive drugs, liquid crystal materials, optical recording materials or photoconductive materials, but how to control the substituents and central ions To obtain the target functional compound, it requires creative work. [0003] Phthalocyanine complex as a photosensitizer in the applicatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/10A61K41/00A61K49/00A61P35/00A61P35/02A61P31/04A61P31/12A61P9/10A61P1/02A61P27/02A61P17/00
Inventor 黄剑东蔡奕滨柯美荣郑碧远
Owner FUZHOU UNIV
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