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BODIPY derivative containing six trifluoromethyl groups and preparation and application of BODIPY derivative

A technology of trifluoromethyl group and fluoroboron dipyrrole, which is applied in the field of synthesis and design of anticancer photosensitizers for photodynamic therapy, can solve problems such as weak tissue penetration ability, uncertain composition, skin phototoxicity, etc. Achieve the effect of not easy skin phototoxicity, low cost, and improving physical and chemical properties

Active Publication Date: 2016-10-12
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The composition of traditional photosensitizers is uncertain, the maximum absorption wavelength is not in the red light region, the tissue penetration ability is weak, and skin phototoxicity is prone to occur during treatment, so the applications are limited

Method used

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  • BODIPY derivative containing six trifluoromethyl groups and preparation and application of BODIPY derivative
  • BODIPY derivative containing six trifluoromethyl groups and preparation and application of BODIPY derivative

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preparation example Construction

[0030] The preparation method of the fluoroboron dipyrrole derivative containing six trifluoromethyl groups comprises the following steps:

[0031] (1) Compound , Add it to 100 mL of anhydrous dichloromethane at a molar ratio of 1:2.5, then add a drop of trifluoroacetic acid (TFA), and stir overnight at room temperature under nitrogen protection; Benzoquinone (DDQ) was dissolved in 150 mL of dichloromethane, and then added to the reaction solution, and the resulting mixture was stirred at room temperature for 4 h; triethylamine (Et 3 N, 12 mL) and boron trifluoride diethyl ether (BF 3 ·Et 2 O, 12 mL) were slowly added dropwise to the above mixture, and stirred overnight at 0 °C; 3 The solution and water were washed twice, and the combined organic layers were washed with anhydrous Na 2 SO 4 After drying, it was spin-dried under reduced pressure; using dichloromethane-petroleum ether (1:2, v / v) as eluent, purified by silica gel column chromatography to obtain compound 1 ...

Embodiment 1

[0036] A preparation method of fluoroboron dipyrrole derivatives containing six trifluoromethyl groups, the specific steps are:

[0037] (1) Compound (1.40 g, 5.78 mmol), (1.22 g, 12.80 mmol) was added to 100 mL of anhydrous dichloromethane, then 0.05 mL of trifluoroacetic acid (TFA) was added, and stirred overnight at room temperature under nitrogen protection; 2,3-dichloro-5,6-dicyano p-Benzoquinone (DDQ) (1.32 g, 5.80 mmol) was dissolved in 150 mL of dichloromethane, then added to the reaction solution, and the resulting mixture was stirred at room temperature for 4 h; triethylamine (Et 3 N, 12 mL) and boron trifluoride diethyl ether (BF 3 ·Et 2 O, 12 mL) were slowly added dropwise to the above mixture, and stirred overnight at 0 °C; 3 The solution and water were washed twice, and the combined organic layers were washed with anhydrous Na 2 SO 4 After drying, it was spin-dried under reduced pressure; using dichloromethane-petroleum ether (1:2, v / v) as eluent, purifie...

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Abstract

The invention discloses a BODIPY derivative containing six trifluoromethyl groups and preparation and application of the BODIPY derivative. The BODIPY derivative has the chemical formula shown in the description. As the trifluoromethyl groups are introduced into a BODIPY photosensitizer, the physical-chemical characteristics of a photosensitive medicine can be changed, the drug effect of the photosensitive medicine is improved, the pharmacokinetics is changed, and the bioavailability and the mtabolic stability of the photosensitive medicine are improved. The BODIPY derivative is simple in synthetic method, easily accessible in raw material, low in cost, high in yield, easy to purify and conductive to industrial production.

Description

technical field [0001] The invention belongs to the field of design and synthesis of anticancer photosensitizers for photodynamic therapy, and specifically relates to a fluoroboron dipyrrole derivative containing six trifluoromethyl groups and its preparation and application. Background technique [0002] Cancer has become the number one killer of human health and the largest public health problem in the world. The economic burden of cancer has also overwhelmed both developed and developing countries. The risk factors of cancer are widespread and persistent, the morbidity and mortality are on the rise, and the epidemic situation is very severe. Malignant tumors not only cause physical harm to patients, but also bring huge economic and mental pressure to patients and their families, and at the same time cause huge losses of labor force and astonishing consumption of social resources. Therefore, the treatment of malignant tumors has become the common concern of all mankind. A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02A61K31/69A61K41/00A61P35/00
CPCA61K41/0057C07F5/022
Inventor 刘见永马家林赵伟桐
Owner FUZHOU UNIV
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