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Bacterial chlorophyll derivative and preparation method thereof

A halogen and drug technology, which is applied in the field of its preparation and bacteriochlorophyll derivatives, can solve the problems of long light avoidance period and slow metabolism of photosensitizers, etc., and achieve the effect of short light avoidance period, good chemical stability and good water solubility

Active Publication Date: 2020-05-19
ZHEJIANG HISUN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the problems of slow metabolism and long light avoidance period of existing photosensitizers, the present invention provides a bacteriochlorophyll derivative with fast metabolism and short light avoidance period, which can be used as a photosensitizer for photodynamic therapy research, and patients can achieve day-to-day Treatment, go home on the same day, thereby reducing the financial burden on patients and their families

Method used

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  • Bacterial chlorophyll derivative and preparation method thereof
  • Bacterial chlorophyll derivative and preparation method thereof
  • Bacterial chlorophyll derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] The synthesis of embodiment 1 compound (I-1)

[0091]

[0092] The first step: the synthesis of methyl 2-(4-hydroxymethyl)phenoxyacetate (IV-1)

[0093] In a 500mL three-necked round-bottomed flask, add p-hydroxybenzaldehyde (10g, 82mmol), then add 120mL of acetonitrile, stir and dissolve, then add methyl bromoacetate (10mL, 105mmol) and potassium carbonate (15g, 9.2mmol), Stir the reaction at room temperature, and monitor the reaction by TLC. After the reaction, add 150 mL of ethyl acetate to dilute the reaction solution, filter, and concentrate the filtrate under reduced pressure to obtain a yellow oil, which is directly carried out to the next step of reaction;

[0094]The obtained yellow oil was transferred to a 500mL three-necked round-bottomed flask, 100mL of dichloromethane and 50mL of methanol were added, stirred, and under ice-bath cooling, sodium borohydride (3.0g, 79mmol) was slowly added. After the addition, Stir the reaction at room temperature, and mon...

Embodiment 2

[0108] The synthesis of embodiment 2 compound (I-2):

[0109]

[0110]

[0111] The first step: the synthesis of methyl 5-(3-methyl-4-hydroxymethyl)phenoxyvalerate (IV-2)

[0112] In a 500mL three-neck round bottom flask, add 3-methyl-4-hydroxybenzaldehyde (5.0g, 36.7mmol), then add 80mL of acetonitrile, stir to dissolve, then add methyl 5-bromovalerate (8.0g, 41.0mmol) and potassium carbonate (7.0g, 50.6mmol), stirred at 60°C, and monitored by TLC. After the reaction, 150mL of ethyl acetate was added to dilute the reaction solution, filtered, and the filtrate was concentrated under reduced pressure to obtain a yellow oil;

[0113] Transfer the obtained yellow oil into a 500mL three-necked round-bottomed flask, add 100mL of dichloromethane and 50mL of methanol, stir, and slowly add sodium borohydride (0.75g, 2.04mmol) under ice-bath cooling. After the addition, Stir the reaction at room temperature, and monitor the reaction by TLC. After the reaction, quench the reactio...

Embodiment 3

[0127] The synthesis of embodiment 3 compound (I-3):

[0128]

[0129]

[0130] The first step: the synthesis of methyl 2-(3-methyl-(4-hydroxymethyl))phenoxyacetate (IV-3)

[0131] In a 500mL three-neck round bottom flask, add 3-methyl-4 hydroxybenzaldehyde (5.02g, 25.5mmol), then add 80mL of acetonitrile, stir and dissolve, then add methyl bromoacetate (2.5mL, 2.55mmol) and Potassium carbonate (5.0g, 3.61mmol), stirring reaction at room temperature, TLC monitoring reaction, after the reaction, add 150mL ethyl acetate to dilute the reaction solution, filter, and concentrate the filtrate to dryness under reduced pressure to obtain a yellow oil, directly proceed to the next step reaction ;

[0132] Transfer the obtained yellow liquid into a 500mL three-necked round-bottomed flask, add 100mL of dichloromethane and 50mL of methanol, stir, and slowly add sodium borohydride (0.7g, 1.9mmol) under ice-bath cooling. Stir the reaction, TLC monitors the reaction, after the reacti...

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Abstract

The invention provides a bacterial chlorophyll derivative, a preparation method and medical applications thereof, and specifically relates to a bacterial chlorophyll derivative represented by a formula (I), a preparation method and a pharmaceutically acceptable salt thereof, and applications of the bacterial chlorophyll derivative and the pharmaceutically acceptable salt in photodynamic therapy oftumors, wherein each substituent in the formula (I) is defined in the specification.

Description

technical field [0001] The invention relates to the field of pharmacy, in particular to a bacterial chlorophyll derivative, a preparation method and application thereof. Background technique [0002] Photodynamic therapy (PDT for short) refers to a treatment method that uses visible light to sensitize photosensitizers located inside human diseased tissues to kill diseased tissues. Clinically, through intravenous injection of photosensitizers that have an affinity for biologically active tissues such as tumor cells, the photosensitizer will be selectively enriched in the lesion area, and then the lesion area will be irradiated with light of a certain wavelength, and the photosensitizer will absorb light energy Afterwards, it transforms into a highly reactive active substance, and with the participation of oxygen, it reacts chemically with biomolecules of diseased tissue to kill them. This is a new clinical treatment technology under research and development, which is mainly ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/22A61K31/439A61P35/00
CPCC07D471/22A61P35/00A61K31/439C07D487/22A61K47/54
Inventor 陈贞亮王川吕志卿马仁超郑晓鹤白骅
Owner ZHEJIANG HISUN PHARMA CO LTD
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