Silicon phthalocyanine axially bonded with piperidine or morpholine derivative with ester bond

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

Active Publication Date: 2015-05-27
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Silicon phthalocyanine axially bonded with piperidine or morpholine derivative with ester bond
  • Silicon phthalocyanine axially bonded with piperidine or morpholine derivative with ester bond
  • Silicon phthalocyanine axially bonded with piperidine or morpholine derivative with ester bond

Examples

Experimental program
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Effect test

Embodiment 1

[0037] Synthesis and physical and chemical properties of bis[3-(N-piperidinyl)propyl ester group]silicone phthalocyanine (structure shown in the following formula):

[0038]

[0039] Under nitrogen protection, add dichlorosilyl 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). Remove the solvent by rotary evaporation in vacuo, dissolve with 100ml of dichloromethane, centrifuge to remove insoluble matter, extract the dichloromethane solution with water (3×100ml), collect the organic layer, then extract with dilute hydrochloric acid (0.1-0.5 mmol), and collect the aqueous layer. The aqueous 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 45%. The maximum absorption peak of the produ...

Embodiment 2

[0042] Synthesis and physical and chemical properties of bis[3-(N-methyl-N-piperidinyl) propyl ester group] silicon phthalocyanine diiodide (structure shown in the following formula):

[0043]

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

[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 ), δ...

Embodiment 3

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

[0048]

[0049] Under the protection of nitrogen, dichlorosilyl phthalocyanine (244.7mg, 0.4mmol), 3-(N-morpholine) propionic acid 1.2-2.4mmol (preferably 2.0mmol) was added to toluene or xylene or dioxane 20 -50ml (preferably toluene, 30ml), reflux for 20-36 hours (preferably 24 hours). Remove the solvent by rotary evaporation in vacuo, dissolve with 100ml of dichloromethane, centrifuge to remove insoluble matter, extract the dichloromethane solution with water (3×100ml), collect the organic layer, then extract with dilute hydrochloric acid (0.1-0.5 mmol), and collect the aqueous layer. The aqueous 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...

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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 in particular relates to a silicon phthalocyanine with an axial ester bond connecting piperidine or morpholine derivatives 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 regulate substituents and central ions To obtain the target functional compound, it requires creative work. [0003] The application prospect of phthalocyanine complexes as ...

Claims

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Application Information

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Patent Type & Authority Applications(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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