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Tetraphenylmethylene chlorin compound, and preparation method and application thereof

A technology of tetraphenylmethylene chlorin and compound, which is applied in the field of tetraphenylmethylene chlorin and its preparation, and can solve the problems of poor stability, difficult synthesis, easy oxidation of Temoporfin and the like

Inactive Publication Date: 2017-06-09
陈志龙
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these tetraphenyl chlorin drugs still have certain disadvantages, such as Temoporfin is easily oxidized, poor in stability, difficult to synthesize, expensive, etc.

Method used

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  • Tetraphenylmethylene chlorin compound, and preparation method and application thereof
  • Tetraphenylmethylene chlorin compound, and preparation method and application thereof
  • Tetraphenylmethylene chlorin compound, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0042] 1. Preparation method of 5,10,15,20-tetraphenyl-[2:3]-[(methoxycarbonyl, carboxyl)-methylene]chlorphine

[0043] In a 100mL three-necked flask, add potassium carbonate (620mg, 4.5mmol), dimethyl malonate (0.64mL, 6.8mmol) and 20mL dimethyl sulfoxide, and raise the temperature to 60°C under a nitrogen atmosphere and stir for about 1h; Then 2-nitro-5,10,15,20-tetraphenylporphyrin (400mg, 0.606mmol) was added and heated to 100°C for about 8 hours. The reaction was monitored by TLC until the reaction was complete. After the reaction solution was cooled to room temperature, 100 mL of water was added, the aqueous phase was extracted with dichloromethane (100 mL×3), and the organic phases were combined. The organic phase was washed with saturated brine (100 mL×3), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was subjected to column chromatography (eluent: dichloromethane:petroleum ether=1:10...

Embodiment 2

[0068] 1. Preparation method of 5,10,15,20-tetraphenyl-[2:3]-{[methoxycarbonyl, (2-hydroxyethyl)carbamoyl]-methylene}chlorphine

[0069] The synthesis of 5,10,15,20-tetraphenyl-[2:3]-[bis(methoxycarbonyl)-methylene]chlorin refers to Example 1.

[0070] In a 100mL three-necked flask, add 5,10,15,20-tetraphenyl-[2:3]-[bis(methoxycarbonyl)-methylene]chlorin (372mg, 0.5mmol), then Add 20mL tetrahydrofuran and 10mL ethanolamine, heat to reflux, and monitor by thin layer chromatography until the reaction is complete. After the reaction solution was cooled to room temperature, 150 mL of dichloromethane was added for extraction. The organic phase was washed with water (100 mL×3), washed with saturated brine (100 mL×3), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was subjected to column chromatography (eluent: dichloromethane:methanol=10:1) to obtain a purple solid powder 5,10,15,20-tetraphenyl-[2:...

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Abstract

The invention relates to a tetraphenylmethylene chlorin compound, and a preparation method and application thereof. The tetraphenylmethylene chlorin compound has a following structure (I) as shown in the description, wherein R1 and R2 located in ortho-positions (o-), meta-positions (m-) or para-positions (p-) of a benzene ring. The invention relates to the field of photosensitive drugs (also named photosensitizers or photodynamic sensitizers) and photodynamic therapy, and in particular to methylene chlorin photosensitizer, and the preparation method and the application thereof in the field of medicine. The tetraphenylmethylene chlorin photosensitizer prepared by the invention has stable chemical property and very strong photodynamic activity and can be used for photodynamic therapy of diseases of tumors, retina macular degeneration, actinic keratoma, nevus flammeus, condyloma acuminata and the like.

Description

technical field [0001] The invention relates to the fields of photosensitizing drugs and photodynamic therapy, in particular to a class of tetraphenylmethylene chlorphine compounds and a preparation method and application thereof. Background technique [0002] Photodynamic therapy (PDT) is a new method for the treatment of tumors, macular degeneration, actinic keratosis, port wine stains, genital warts and other diseases. Since entering clinical research in the 1970s, PDT has made remarkable achievements in clinical treatment because of its good selectivity, low toxicity, good reproducibility, safety, minimal invasiveness, synergy and Advantages such as relatively low cost stand out, showing huge potential and strong vitality. [0003] The principle of photodynamic therapy is that after the photosensitizer enters the body, it selectively gathers in the target tissue along with the blood circulation, and then directly irradiates the tumor tissue with a laser of a certain wav...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61P35/00A61P27/02A61P17/00A61P31/20A61P17/12
CPCC07D487/22A61K41/0071
Inventor 陈志龙廖平永汪新荣高迎华张向化吴忠明张立新陈娜鲍蕾蕾郑梅珍王力王红弟朱维
Owner 陈志龙
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