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Derivative of anti-tumor photosensitizer ALA hybrid 3-hydroxypyridin-4H-one as well as preparation method and application of derivative

A technology of hydroxypyridine and photosensitizer, applied in the field of coupling derivatives of hydroxypyridone and 5-aminolevulinic acid, which can solve the problems of long distribution duration, loss of toxicity, and poor pharmacokinetic performance

Active Publication Date: 2020-12-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, iron chelation strategies in modern anticancer chemotherapy have attracted great interest, but iron in cells is always chelated by various molecules, but this does not make it less toxic because chelated iron is still able to Generate active oxygen
After deferoxamine is used as a heme synthesis inhibitor, it is found that it has certain selectivity and can increase the accumulation of PpIX, but its pharmacokinetic performance is poor, which makes its distribution last longer. Secondly, due to deferoxamine With strong antioxidant activity under this condition, higher DFO concentrations may adversely affect the formation of PpIX

Method used

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  • Derivative of anti-tumor photosensitizer ALA hybrid 3-hydroxypyridin-4H-one as well as preparation method and application of derivative
  • Derivative of anti-tumor photosensitizer ALA hybrid 3-hydroxypyridin-4H-one as well as preparation method and application of derivative
  • Derivative of anti-tumor photosensitizer ALA hybrid 3-hydroxypyridin-4H-one as well as preparation method and application of derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069]

[0070] Add raw material ethyl maltol (7.56g, 60mmol) in 250mL round bottom flask, anhydrous K 2 CO 3 (9.12g, 66mmol), benzyl bromide (10.78g, 63mmol) and acetone (150mL), the reaction system was heated to reflux, and the reaction progress was monitored by TLC. After the reaction was completed, the mixture was cooled to room temperature. The reaction solvent was concentrated in vacuo, water (100 mL) was added, and the mixture was extracted with dichloromethane (50 mL×5), the organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a yellow oily hydroxyl-protected pyrone (13.1 g), the yield was 85-90%.

[0071] Dissolve NaOH (0.64g, 16mmol) in H 2 O: EtOH (2:1) mixed solution (100mL), after the solid dissolved, add yellow oily hydroxyl-protected pyrone (1.50g, 6.5mmol) and NH 2 CH 2 COOH (0.525g, 7mmol), then the reaction mixture was refluxed at 75°C for 8h. After the reaction, ethanol ...

Embodiment 2

[0077]

[0078] Add ethyl maltol (7.56g, 60mmol) in 250mL round bottom flask, anhydrous K 2 CO 3 (9.12g, 66mmol), benzyl bromide (10.78g, 63mmol) and acetone (150mL), the reaction system was heated to reflux, and the reaction progress was monitored by TLC. After the reaction was completed, the mixture was cooled to room temperature. The reaction solvent was concentrated in vacuo, water (100 mL) was added, and the mixture was extracted with dichloromethane (50 mL×5), the organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a yellow oily intermediate (13.1 g ), the yield is 90%.

[0079] Dissolve NaOH (0.64g, 16mmol) in H 2 O:EtOH (2:1) mixed solution (100mL), after the solid is dissolved, add the intermediate obtained above (1.50g, 6.5mmol) and Boc-L-Lys-OH (0.525g, 7mmol), and then react The mixture was refluxed at 75 °C for 8 h. After the reaction, ethanol was distilled off under reduced p...

Embodiment 3

[0087]

[0088] Add ethyl maltol (7.56g, 60mmol) in 250mL round bottom flask, anhydrous K 2 CO 3 (9.12g, 66mmol), benzyl bromide (10.78g, 63mmol) and acetone (150mL), the reaction system was heated to reflux, and the reaction progress was monitored by TLC. After the reaction was completed, the mixture was cooled to room temperature. The reaction solvent was concentrated in vacuo, water (100 mL) was added, and the mixture was extracted with dichloromethane (50 mL×5), the organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a yellow oily intermediate (13.1 g ), the yield is 90%.

[0089] Dissolve NaOH (0.64g, 16mmol) in H 2 O:EtOH (2:1) mixed solution (100mL), after the solid is dissolved, add the intermediate obtained above (1.50g, 6.5mmol) and Boc-L-Lys-OH (0.525g, 7mmol), and then react The mixture was refluxed at 75 °C for 8 h. After the reaction, ethanol was distilled off under reduced p...

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Abstract

The invention provides a derivative of an anti-tumor photosensitizer ALA hybrid 3-hydroxypyridin-4H-one, a preparation method of the derivative and an application of the derivative in preparation of aphotodynamic therapy drug. The derivative of the anti-tumor photosensitizer ALA hybrid 3-hydroxypyridin-4H-one is a compound as shown in a formula (I), a formula (II) or a formula (III) and a pharmaceutically acceptable salt of the compound.

Description

technical field [0001] The invention relates to a derivative coupled with hydroxypyridone and 5-aminolevulinic acid (ALA) with iron ion chelating ability, a preparation method and photodynamic application thereof. Background technique [0002] Traditional tumor treatment methods mainly include surgery, chemotherapy and radiotherapy, etc., but there are some serious defects in these treatment methods. In recent years, with the development of medical technology, photodynamic therapy (PDT) has gradually entered people's field of vision. PDT is the use of visible light to activate exogenously administered or endogenously formed photosensitive substances in the presence of molecular oxygen. , a photosensitizer after light activation, whose photosensitization leads to the formation of singlet oxygen, a strong oxidant that can lead to damage to a variety of subcellular substrates and cell death. Through the study of its mechanism of action, it is found that photosensitizer is a ke...

Claims

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Application Information

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IPC IPC(8): A61K41/00A61K47/54A61P35/00C07D213/69C07K5/097
CPCA61K41/0061A61K47/545A61P35/00C07D213/69C07K5/0821Y02P20/55
Inventor 谢媛媛张雨佳袁圣利
Owner ZHEJIANG UNIV OF TECH
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