Intermediary tetrasubstituted chlorin compound and application thereof in the field of medicines

A technology of chlorin and compounds, which is applied in the field of chlorin compounds, can solve the problems of insufficient stability and easy oxidation, and achieve the effects of improving stability, improving fat solubility and water solubility, and good selective absorption

Inactive Publication Date: 2012-10-10
SHANGHAI XIANHUI MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs still have some shortcomings, such as the presence of phenolic hydroxyl groups around Temoporfin, which are easily oxidized and not stable enough

Method used

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  • Intermediary tetrasubstituted chlorin compound and application thereof in the field of medicines
  • Intermediary tetrasubstituted chlorin compound and application thereof in the field of medicines
  • Intermediary tetrasubstituted chlorin compound and application thereof in the field of medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 1. Synthesis experiment of raw materials

[0025] (1) 5,10,15,20-tetrakis-(4-methoxycarbonylbutyl)-porphine

[0026] Synthesis of (5,10,15,20-tetrakis(4-methoxycarbonylbutyl)-21H,23H-Porphine):

[0027]

[0028]

[0029] Weigh 12g of montmorillonite k10 into a 500mL three-neck flask and put it into an oven for activation at 120°C for 3 hours, then take it out, set up a reflux device, fill it with nitrogen, and wrap the bottle wall with aluminum foil to avoid light. Add 350 mL of dichloromethane and 10 mL of dichloromethane dissolved in 5-methoxycarbonyl-1-pentanal (3.2 g, 21 mmol), and stir for half an hour. With thorough stirring, pyrrole (1.52 mL, 22 mmol) was slowly added dropwise at room temperature, and stirring was continued for 1 hour. Then chloranil (3.87g, 15.75mmmol) was added and refluxed at 45°C for 1 hour. The solid powder was removed by filtration, and the filter cake was washed with ethyl acetate until it was colorless. The filtrate was spin-dri...

Embodiment 2

[0049] 1. Photodynamic anti-proliferation experiment of photosensitizers on colon cancer SW480 cells

[0050] Tested cells: colon cancer cells SW480

[0051] Test drug: a synthetic new photosensitizer, hematoporphyrin derivative HpD (produced by Beijing Institute of Pharmaceutical Industry).

[0052] Light source: MTZ-1 pulse laser cancer treatment machine; SD2490 laser power measuring instrument.

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Abstract

The invention relates to a chlorin compound of which an intermediary site is substituted by 4-carboxyl butyl, a preparation method of the chlorin compound, and application of the chlorin compound in the field of medicines. The preparation method comprises the following steps: (1) with pyrrole and 5-methoxycarbonyl-1-valeraldehyde as raw materials, synthesizing an important intermediate 5,10,15,20-4-(4-methoxycarbonylbutyl)-porphine; (2) in an organic solvent medium, hydrolyzing the 5,10,15, 20-4-(4-methoxycarbonylbutyl)-porphine under an alkaline condition to obtain 5,10,15,20-4-(4-carboxybutyl)-porphine; (3) reducing the 5,10,15,20-4-(4-carboxybutyl)-porphine, and performing column chromatographic separation to obtain a target compound. The target compound, as a photosensitizer, is mainly applied to treatment of tumors, port wine stains and other diseases.

Description

technical field [0001] The invention belongs to the field of chlorin compounds, and in particular relates to a chlorin compound whose meso position is substituted by 4-carboxybutyl, its preparation method and its application in the field of medicine. Background technique [0002] Photodynamic therapy (PDT) is one of the most promising new technologies developed in the past 20 years. Since entering clinical research in the 1970s, breakthroughs have been made in the treatment of tumors. At present, photodynamic therapy is not only limited to the treatment of malignant tumors, but also shows good prospects in the treatment of many other diseases. [0003] In photodynamic therapy, photosensitizers play a decisive role as energy carriers and reaction bridges. The first generation photosensitizer is represented by photofrin II, the first photosensitizer listed in the Netherlands in 1993, which is a complex mixture of hematoporphyrin derivatives, and its indication is tumor; the s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61K31/409A61P35/00A61P17/00
Inventor 陈志龙叶颖严懿嘉陈珍琰
Owner SHANGHAI XIANHUI MEDICAL TECH
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