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Perylene quinone compounds and their preparation methods and applications

A compound and drug technology, which is applied in the field of fluorescence diagnosis and photodynamic drug, can solve the problem that the photosensitizer needs to be further improved, and achieve the effect of no scar treatment, fast metabolism and short treatment time

Active Publication Date: 2022-03-29
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, the performance of the above-mentioned photosensitizers such as singlet quantum efficiency or discrimination in detection still needs to be further improved

Method used

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  • Perylene quinone compounds and their preparation methods and applications
  • Perylene quinone compounds and their preparation methods and applications
  • Perylene quinone compounds and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Embodiment 1, preparation Hypocretin 488 (H488)

[0098] 0.60g (4.3×10 -3 mol) potassium carbonate was dissolved in 40.0mL N,N-dimethylformamide (DMF), and Hypocretin A (HA) 25.0mg (4.58×10 -5 mol) was added to the above solution. After fully dissolving, argon gas was introduced, heated at 130°C in the dark, and reacted with electromagnetic stirring for 1.5 hours. After the reaction was completed, the reaction solution was drained under reduced pressure in a water bath at 75°C, neutralized with an appropriate amount of dilute hydrochloric acid, extracted three times with chloroform, washed with water until neutral, and distilled under reduced pressure to obtain an orange powder. Chloroform-petroleum ether (30-60° C.) was recrystallized repeatedly twice to finally obtain 20.8 mg of pure hypocretin 488 (H488) as an orange-red powder with a yield of 93.1%.

[0099] The structural characterization data of this product are as follows:

[0100] UV spectrum λmax (CHCl 3 )...

Embodiment 2

[0111] Embodiment 2, preparation Hypocretin 460 (H460)

[0112] 0.70g (6.6×10 -3 mol) sodium carbonate and 0.12g (8.7×10 -4 mol) potassium oxide was dissolved in 50mL N,N-dimethylformamide (DMF), and Hypocretin B (HB) 40.0mg (7.7×10 -5 mol), added to the above solution. After fully dissolving, argon was introduced, heated at 136°C in the dark, and reacted with electromagnetic stirring for 4.5 hours. After the reaction is completed, drain the reaction solution in a water bath at 75°C under reduced pressure, add 200mL of water, and react with electromagnetic stirring at room temperature in the dark for 16 hours, neutralize with an appropriate amount of dilute hydrochloric acid, extract with dichloromethane three times, wash with water until neutral, and distill under reduced pressure to obtain an orange color powder. Chloroform-petroleum ether (60° C.) was recrystallized several times to obtain 28.9 mg of orange-red powder Hypocretin 460 (H460), with a yield of 83.2%.

[01...

Embodiment 3

[0126] Embodiment 3, preparation Hypocretin 445 (H445)

[0127] 3.0g (2.2×10 -2 mol) potassium carbonate was dissolved in 60mL N,N-dimethylformamide (DMF), and Hypocretin A (HA) 44.0mg (8.1×10 -5 mol) was added to the above solution. After thorough mixing, argon was introduced, heated at 151°C in the dark, and reacted with electromagnetic stirring for 7.5 hours. The reaction solution was drained under reduced pressure in a water bath at 75°C, neutralized with an appropriate amount of dilute hydrochloric acid, extracted several times with chloroform, the combined extracts were washed with water until neutral, and an orange powder was obtained by distillation under reduced pressure. Repeated recrystallization from acetone-petroleum ether (30-60° C.) finally obtained 30.0 mg of orange-red powder hypocretin 445 (H445), with a yield of 83.6%.

[0128] The structural characterization data of this product are as follows:

[0129] UV spectrum λmax (CHCl 3 ): 336.5nm, 468.5nm, 534...

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Abstract

The compound represented by formula I, its stereoisomer, racemate, tautomer, isotopic label, polymorph, prodrug, or its pharmaceutically acceptable salt, wherein, R 1 , R 2 same or different, independently selected from H, C 1‑12 Alkyl, C 1‑12 Alkoxy, ‑COC 1‑12 Alkyl, C 3‑20 Cycloalkyl, or R 1 , R 2 co-form = O; R 3 , R 4 , R 5 , R 6 same or different, independently selected from H, OH, C 1‑12 Alkyl, C 1‑12 Alkoxy or ‑COC 1‑12 alkyl. The compound represented by formula I maintains all the excellent properties of natural oleocanthal and significantly improves the quantum yield.

Description

technical field [0001] The invention belongs to the technical field of fluorescence diagnosis and photodynamic medicine, and specifically relates to perylenequinone compounds and their preparation methods and applications. Background technique [0002] Perylenequinones are a class of natural phytochromes distributed in nature, including hypocrellin and scaboclavin. As a new type of photosensitizer or phototherapy drug, it has a good photodynamic killing effect on tumor cells, so it has received great attention. [0003] Hypocrellin (Hypocrellin) is a natural photosensitizer extracted from a parasitic fungus-Hypocrella bambuase that parasitizes Arrow bamboo in Yunnan and other places in my country. It belongs to 3,10-dihydroxy-4, 9-perylenequinones. Hypocretin can be used for phototherapy of vulvar white lesions and softening hypertrophic scars (Yu Lanfu, Luo Zihua, Zhang Shengquan, Chinese Journal of Obstetrics and Gynecology, 1984, 1, 19-31; Liang Ruiyuan, Mei Guodong, Zhu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C50/38C07C50/36C07C46/00C07C46/10C09K11/06A61K41/00A61K49/00A61K31/122A61P17/00A61P9/14A61P9/00A61P35/00
CPCC07C50/38C07C50/36A61K41/0057A61P35/00A61K49/0021C07C2603/54C07B2200/13
Inventor 谢杰
Owner INST OF CHEM CHINESE ACAD OF SCI
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