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Psoralen schiff base derivatives and application

A technology of Schiff bases and psoralen is applied in the directions of drug combinations, medical preparations containing active ingredients, organic active ingredients, etc. Problems such as weak research on material basis

Active Publication Date: 2017-03-29
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 schiff base derivatives and application
  • Psoralen schiff base derivatives and application
  • Psoralen schiff base derivatives and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Preparation of Intermediate 2:

[0079] 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;

[0080] NMR data of 4-methyl-7-hydroxyethoxycoumarin (intermediate 2):

[0081] 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);

[0082] Preparation of intermediate 3:

[0083] Under low-temperature reaction conditions of -78°C, dissolve 50.25g (2mmol) oxalyl chloride in a small amount of dry dichloromethane, and slowly add dropwi...

Embodiment 2

[0100] Preparation of compound 6b:

[0101] Compound 2-compound 5 were prepared according to Example 1:

[0102] Dissolve 0.21g (1mmol) of compound 5 and 0.16g (1.5mmol) of 4-methylaniline in absolute ethanol, reflux the reaction until all the raw materials disappear, cool to room temperature, concentrate the mother liquor, and elute the residue by column chromatography gradient , the eluent is petroleum ether:ethyl acetate with a volume ratio of 15:1, to obtain 0.11g of compound 6b, (Z)-5-(4-methylphenylimine)methyl-7H-fur[3, 2-g] benzopyran-7-one;

[0103] NMR data of (Z)-5-(4-methylphenylimine)methyl-7H-furo[3,2-g]benzopyran-7-one (compound 6b):

[0104] 1 H NMR (400MHz, CDCl 3 )δ9.18(s,1H),8.67(s,1H),7.70(d,J=2.2Hz,1H),7.54(s,1H),7.05(d,J=8.1Hz,2H),6.90– 6.85(m,3H),6.77(s,1H),2.42(s,3H).

[0105] 13 C NMR (151MHz, CDCl 3 )δ 161.19, 156.35, 152.60, 148.19, 147.01, 146.27, 138.29, 130.24, 125.14, 121.21, 119.60, 118.35, 116.04, 113.42, 107.14, 100.17, 21.31.

Embodiment 3

[0107] Preparation of compound 6c:

[0108] Compound 2-compound 5 were prepared according to Example 1:

[0109] Dissolve 0.21g (1mmol) of compound 5 and 0.19g (1.5mmol) of 4-chloroaniline in absolute ethanol, reflux the reaction until all the raw materials disappear, cool to room temperature, concentrate the mother liquor, and elute the residue by column chromatography gradient, The eluent is petroleum ether:ethyl acetate with a volume ratio of 15:1, and 0.09 g of compound 6c is obtained, and compound 6c is (Z)-5-(4-chlorophenylimine)methyl-7H-furan[3 ,2-g]benzopyran-7-one;

[0110] NMR data of (Z)-5-(4-chlorophenylimine)methyl-7H-furo[3,2-g]benzopyran-7-one (compound 6c):

[0111] 1 H NMR (600MHz, CDCl 3 )δ9.13(s,1H),8.64(s,1H),7.71(d,J=2.0Hz,1H),7.55(s,1H),7.45(d,J=7.4Hz,2H),7.28( d,J=8.2Hz,2H),6.89(d,J=1.9Hz,1H),6.78(s,1H).

[0112] 13 C NMR (151MHz, CDCl 3 )δ 160.84, 157.72, 147.23, 146.99, 145.68, 138.10, 133.61, 129.65, 125.06, 124.42, 122.36, 113.02, 119.28, 11...

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Abstract

The invention relates to psoralen schiff base derivatives and an application. The compounds are 4-methyl-7-hydroxycoumarin (which is an intermediate 1), 4-methyl-7-hydroxyethoxycoumarin (which is an intermediate 2), 4-methyl-7-formylmethoxycoumarin (which is an intermediate 3), 5-methyl-7H-furan[3,2-g]benzopyran-7-one (which is a compound 4), 7-oxo-7H-furan[3,2-g]benzopyran-5-formaldehyde (which is a compound 5), and a compound 6a-6k. The fact that the 11 psoralen schiff base derivatives affect generation of melanin in mouse B16 cells and inhibit candida albicans, escherichia coli, and staphylococcus aureus is studied. The resultant compounds 6a-6b, 6d-6f and 6j-6k can be applied to prepare medicines for treating vitiligo in the clinic. The obtained psoralen schiff base derivatives can be used for preparing medicines for treating candida albicans infection in the clinic, and the compounds 6b-6c, 6e-6h and 6h-6k can be used for preparing medicines for treating staphylococcus aureus infection in the clinic.

Description

technical field [0001] The present invention relates to a psoralen Schiff base derivative and its use. The compound has been screened for anti-vitiligo and antibacterial activity. Compounds 6a-6b, 6d-6f, and 6j-6k can all be used in the clinical preparation of medicines for the treatment of vitiligo. Use in medicine. All psoralen Schiff base derivatives can be used in the clinical preparation of medicines for the treatment of Candida albicans (Candida albicans) infection, and compounds 6b-6c, 6e-6h, and 6k can also be used in the clinical preparation of treatments Use in medicine for Staphylococcus aureus 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04A61K31/366A61P31/04A61P17/00
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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