Preparation method of di-((3-chlorobenzothiophene-2-ester) hexafluorophenoxy) axially substituted silicon phthalocyanine

A technology of hexafluorophenoxy and chlorobenzothiophene is applied in chemical instruments and methods, medical preparations containing active ingredients, pharmaceutical formulations, etc., to achieve the effects of increasing penetrating ability, increasing solubility, and increasing permeability

Inactive Publication Date: 2021-03-30
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Finally, there is no report about the axial substitution of arylthiophene silicon phthalocyanine at home and abroad

Method used

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  • Preparation method of di-((3-chlorobenzothiophene-2-ester) hexafluorophenoxy) axially substituted silicon phthalocyanine
  • Preparation method of di-((3-chlorobenzothiophene-2-ester) hexafluorophenoxy) axially substituted silicon phthalocyanine
  • Preparation method of di-((3-chlorobenzothiophene-2-ester) hexafluorophenoxy) axially substituted silicon phthalocyanine

Examples

Experimental program
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Effect test

Embodiment 1

[0023] 1) dichlorosilicon phthalocyanine (abbreviated as SiPcCl in the present invention 2 )Synthesis

[0024] Add 1,3-diiminoisoindoline (7.28g, 50.15mmol), silicon tetrachloride 8.3mL and quinoline 83mL respectively into a three-necked flask, stir and reflux at 220°C for 30min, cool to room temperature, and It was poured into 500mL of methanol solution, stirred and left for about 1 hour, filtered, and the filter residue was washed with 35mL of acetone, methanol, dichloromethane, methanol and other solvents. After drying, 3.6759g of a purple solid was obtained, with a yield of 48.62%.

[0025] 2) Synthesis of 3-chloro-benzothiophene-2-ester-based hexafluorophenol (abbreviated as CBT-OH in the present invention)

[0026] 0.425 g (2 mmol) of 3-chlorobenzothiophene-2-carboxylic acid, 0.67 g (2 mmol) of hexafluorobisphenol A in 70 mg (0.6 mmol) of 4-diaminopyridine, 1 -Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.5g, 2.6mmol) and dichloromethane (40mL), stirred at...

Embodiment 2

[0032] The specific steps are the same as in Example 1: in the process, the amount of 3-chlorobenzothiophene-2-carboxylic acid is 0.850 g (4 mmol), the amount of hexafluorobisphenol A is 0.134 g (4 mmol), and the reaction temperature is 90 ° C. Other reaction conditions were the same, and 0.22 g of ginger green liquid product was obtained with a yield of 21.2%.

[0033] The specific steps are the same as in Example 1: in the process, the amount of 3-chloro-benzothiophene-2-ester-based hexafluorophenol is 0.232g (0.4mmol), the amount of dichlorosilicon phthalocyanine is 0.12g (0.2mmol), and no water Potassium carbonate changed to K 2 CO 3 1.2g (9mmol), the reaction temperature was changed to 130°C. Other reaction conditions were the same, and 0.82 g of white fluffy product was obtained, yield: 44%.

Embodiment 3

[0035] The specific steps are the same as in Example 1: in the process, the dosage of 3-chlorobenzothiophene-2-carboxylic acid is 1.7g (8mmol), and the dosage of hexafluorobisphenol A is 0.134g (4mmol). The reaction temperature is changed to 110°C. Other reaction conditions were the same, and 0.25 g of the ginger green liquid product was obtained with a yield of 23%.

[0036] The specific steps are the same as in Example 1: in the process, the consumption of 3-chloro-benzothiophene-2-ester base hexafluorophenol is 0.464g (0.8mmol), and the consumption of dichlorosilicon phthalocyanine is 0.12g (0.2mmol). The temperature was changed to 150°C. Other reaction conditions were the same, and 0.90 g of white fluffy product was obtained, yield: 46.4%.

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Abstract

The invention belongs to the field of complexes, and particularly belongs to a method for preparing di ((3-chlorobenzothiophene-2-ester) hexafluorophenoxy) axially substituted silicon phthalocyanine,and the complex is applied to photodynamic therapy of bacterial infection as a photosensitizer. The method is realized through the following steps: mixing and stirring 3-chlorobenzothiophene-2-ester hexafluorophenol (CBT-OH for short) and dichlorosilane (IV) phthalocyanine according to a ratio of 1: (0.25-4) at 140 DEG C in toluene in the presence of anhydrous K2CO3, and performing refluxing to prepare di-((3chlorobenzothiophene-2-ester) hexafluorophenoxy) axially substituted silicon phthalocyanine. According to the invention, the steric hindrance of lipophilic chlorobenzothiophene ring structure molecules with large volume can be utilized to inhibit the formation of phthalocyanine aggregates to a certain extent, inhibit the formation of aggregates and increase the permeability of bacterial cell membranes, so that the aryl thiophene axially substituted silicon phthalocyanine complex becomes a photosensitizer with application potential.

Description

technical field [0001] The invention belongs to the field of complexes, in particular to a method for preparing bis-((3-chlorobenzothiophene-2-ester) hexafluorophenoxy) axially substituted silicon phthalocyanine. The complex is used as a photosensitizer for photosensitive Power therapy for bacterial infections. Background technique [0002] Photodynamic therapy (PDT) is a method of treatment for neoplastic and non-neoplastic diseases. The mechanism of photodynamic therapy is that wavelength-matched photosensitizer molecules generate singlet oxygen that damages cells and subsequently induces cell death. Due to the advantages of stable structure and easy modification, maximum absorption wavelength in the range of 600-800nm, easy penetration into human tissue, and high quantum yield of singlet oxygen, metal phthalocyanine complexes have become a promising second-generation photosensitizer. . However, due to the easy aggregation between phthalocyanine molecules and limited ce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10A61K41/00A61P31/04
CPCC07F7/10A61K41/0076A61P31/04
Inventor 彭亦如黄秉成黄义德
Owner FUJIAN NORMAL UNIV
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