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Psoralen ester derivatives and applications thereof

A technology of psoralen and its derivatives, which can be applied in drug combinations, skin diseases, and vector-borne diseases, etc. It can solve the problems of weak material basis research, unclear mechanism of action and metabolic process in vivo and in vitro, and constraints on secondary development, etc. question

Active Publication Date: 2017-04-19
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although Uyghur medicine has a remarkable effect and advantages in treating vitiligo, its material basis research is weak, and its mechanism of action and metabolic process in vivo and in vitro are not clear, which seriously restricts its secondary development

Method used

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  • Psoralen ester derivatives and applications thereof
  • Psoralen ester derivatives and applications thereof
  • Psoralen ester derivatives and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Preparation of intermediate 2:

[0088] At room temperature, dissolve 1.76g (10mmol) of intermediate 1 and 2.76g (20mmol) of potassium carbonate in 50mL of acetone, then add 1.20g (15mmol) of 2-chloroethanol, heat to reflux and react until all the raw materials disappear , stop the reaction, cool to room temperature, filter, the filtrate is concentrated, the residue is eluted by column chromatography gradient, the eluent is petroleum ether: ethyl acetate with a volume ratio of 1:1, and 2.10g of intermediate 2,4- Methyl-7-hydroxyethoxycoumarin;

[0089] NMR data of 4-methyl-7-hydroxyethoxycoumarin (intermediate 2):

[0090] 1 H NMR (400MHz, CDCl 3 )d 7.51(d, J=9.0Hz, 1H), 6.91–6.83(m, 2H), 6.15(d, J=1.1Hz, 1H), 4.15(t, J=8.7Hz, 2H), 4.01(m ,2H),2.40(d,J=1.1Hz,3H).

[0091] Preparation of intermediate 3:

[0092] Under low-temperature reaction conditions at a temperature of -78°C, dissolve 50.25 g (2 mmol) of oxalyl chloride in a small amount of dry dichloromethane,...

Embodiment 2

[0117] Preparation of compound 8b:

[0118] The preparation of compound 2-compound 7 is carried out according to embodiment 1:

[0119] Under ice-bath conditions, 0.22g (1mmol) compound 6, 0.21g (1mmol) dicyclohexylcarbodiimide (DCC), 0.12g (1mmol) 4-dimethylaminopyridine (DMAP) and 0.16g (1.2 mmol) 2-methylbenzoic acid was dissolved in an appropriate amount of dichloromethane, fully stirred to make it completely dissolved, moved to room temperature to continue the reaction, after all the raw materials disappeared, filtered, and the mother liquor was successively washed with 1M hydrochloric acid solution and saturated hydrogen carbonate The sodium solution was washed, dried and concentrated, and the residue was eluted by gradient column chromatography, and the eluent was petroleum ether:ethyl acetate at a volume ratio of 15:1, to obtain 0.31g of compound 8b, (7-oxo-7H- Furo[3,2-g]benzopyran-5-)methyl-(2-methyl)benzoate;

[0120] NMR data of (7-oxo-7H-furo[3,2-g]benzopyran-5-...

Embodiment 3

[0124] Preparation of compound 8c:

[0125] Compound 2-Compound 7 were prepared according to Example 1.

[0126] Under ice-bath conditions, 0.22g (1mmol) compound 6, 0.21g (1mmol) dicyclohexylcarbodiimide (DCC), 0.12g (1mmol) 4-dimethylaminopyridine (DMAP) and 0.18g (1.2 mmol) 4-methoxybenzoic acid was dissolved in an appropriate amount of dichloromethane, fully stirred to make it completely dissolved, moved to room temperature to continue the reaction, after all the raw materials disappeared, filtered, and the mother liquor was successively washed with 1M hydrochloric acid solution and saturated carbonic acid Sodium hydrogen solution was washed, dried, concentrated, and the residue was eluted by gradient column chromatography, and the eluent was petroleum ether:ethyl acetate with a volume ratio of 15:1, to obtain 0.32g of compound 8c, (7-oxo-7H - Furo[3,2-g]benzopyran-5-)methyl-(4-methoxy)benzoate;

[0127] NMR data of (7-oxo-7H-furo[3,2-g]benzopyran-5-)methyl-(4-methoxy)be...

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Abstract

The invention relates to psoralen ester derivatives and applications thereof; the compounds comprise 4-methyl-7-hydroxy coumarin (an intermediate 1), 4-methyl-7-hydroxyethoxy coumarin (an intermediate 2), 4-methyl-7-formyl methoxy coumarin (an intermediate 3), 5-methyl-7H-furan[3,2-g]benzopyran-7-one (a compound 4), 7-oxo-7H-furan[3,2-g] benzopyran-5-formaldehyde (a compound 5), 5-hydroxymethyl-7H-furan[3,2-g]benzopyran-7-one (a compound 6), (7-oxo-7H-furan[3,2-g]benzopyran-5-yl)methyl acetate (a compound 7) and compounds 8a-8p. The 20 psoralen ester derivatives have influence on generation of melanin in mouse B16 cells and have the inhibitory effect on candida albicans, escherichia coli and staphylococcus aureus. The compounds 4-7, the compounds 8a-8d and the compounds 8k-8o are used for preparation of drugs for treating leucoderma. The obtained psoralen Schiff base derivatives are used for preparation of drugs for treatment of candida albicans infection, and the compound 5 and the compound 7 are also used for preparation of drugs for treatment of staphylococcus aureus infection.

Description

technical field [0001] The present invention relates to a kind of psoralen ester derivatives and its use, especially related to the anti-vitiligo and antibacterial activity screening of these compounds, all psoralen ester derivatives can be used for clinical preparation and treatment of Candida albicans ) infection; all the remaining 13 compounds except 8e-8j, 8p can be used for the clinical preparation of medicines for the treatment of vitiligo; and compounds 5 and 7 can also be used for the clinical preparation of medicines for the treatment of Staphylococcus aureus (Staphylococcusaureus) infection . Background technique [0002] Vitiligo is a common spontaneous or idiopathic depigmentation skin disease, known as one of the three chronic skin diseases in the world, afflicting more than 50 million patients worldwide. The incidence rate varies from 0.1% to 8% in different regions and different races in the world. The prevalence rate of the general population in my country i...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61P31/10A61P31/04A61P17/00
CPCC07D493/04Y02A50/30
Inventor 阿吉艾克拜尔·艾萨牛超
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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