Carbazole alkamine compound and preparation method thereof and application for parasitic disease resistance

A compound, carbazole technology, applied in the application field of anti-parasitic disease, can solve the problems of high cost, secondary infection, allergic reaction and the like

Active Publication Date: 2017-03-22
STATION OF VIRUS PREVENTION & CONTROL CHINA DISEASES PREVENTION & CONTROL CENT +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, surgery has disadvantages such as easy recurrence, high cost, easy to cause secondary infection and allergic reaction; and statistics show that the cure rate of clinical first-line drug albendazole is only about 30%.
[0006] In summary, ther...

Method used

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  • Carbazole alkamine compound and preparation method thereof and application for parasitic disease resistance
  • Carbazole alkamine compound and preparation method thereof and application for parasitic disease resistance
  • Carbazole alkamine compound and preparation method thereof and application for parasitic disease resistance

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preparation example Construction

[0138] In the present invention, a preparation method of a compound of formula A comprises steps:

[0139]

[0140] (a) in an aprotic polar solvent, in the presence of a base, the substituted carbazole shown in formula I is reacted with epichlorohydrin to obtain a compound of formula II; and

[0141] (b) in a protic polar solvent, under Lewis acid catalysis, the formula II compound and HNR 1 R 2 Carry out the reaction, thereby obtain formula A compound;

[0142] In the above formulas, X, Y, R 1 and R 2 is defined as above.

[0143] In another preferred example, the method includes:

[0144] (1) In an aprotic polar solvent, under basic conditions, the substituted carbazole I is reacted with epichlorohydrin to obtain compound II, which is usually carried out with acetonitrile, acetone, dimethyl sulfoxide, dimethyl Formamide, etc. are used as solvents, and the bases used are triethylamine, diethylamine, pyridine, cesium carbonate, lithium hydroxide, potassium hydroxide, ...

Embodiment 1

[0182] Embodiment 1, 3,6-dichloro-9-epoxypropyl carbazole (IIa):

[0183] 3,6-Dichlorocarbazole (470mg, 2mmol) was dissolved in 20mL DMF, and potassium hydroxide (135mg, 2.4mmol) was slowly added under ice-bath conditions, and stirred for 0.5-1 hour after the addition, until the potassium hydroxide was solid completely dissolved.

[0184] Then epichlorohydrin (2.4 mmol) was slowly added dropwise into the system, and reacted for 4-5 hours. After the reaction, add 30ml of water, extract with ethyl acetate (30ml×3), wash with saturated sodium chloride solution (30ml×3), dry the organic layer with anhydrous sodium sulfate, filter, and recover the solvent from the filtrate under reduced pressure, the crude product Purified by column chromatography to obtain 293 mg of white solid, yield 50%.

Embodiment 2

[0185] Embodiment 2, 9-epoxypropyl carbazole (IIb):

[0186] Refer to Example 1 for the operation process, and replace 3,6-dichlorocarbazole with carbazole to obtain a white solid with a yield of 70%.

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Abstract

The invention provides a carbazole alkamine compound and a preparation method thereof and application for a parasitic disease resistance aspect. Specifically, the invention provides a racemic modification of the compound shown as type (A) and an enantiomer or salt capable of being accepted by pharmacy of the enantiomer. The compound has excellent anti-schistosoma and anti-hydatid cyst activity. According to the carbazole alkamine compound and the preparation method thereof and the application for the parasitic disease resistance aspect, the design is reasonable, the source of used raw materials is wide, the preparation method is easy and convenient and suitable for utility and can be applied to parasitic disease resistance drug preparation. Type A (please see the specifications for the chemical structural formula)

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a novel carbazole aminoalcohol compound, its preparation method and its application in anti-parasitic diseases. Background technique [0002] Schistosomiasis is a zoonotic parasitic disease that seriously endangers human health and affects social and economic development. According to the statistics of the World Health Organization, schistosomiasis ranks first among water-borne diseases and is one of the diseases with the widest geographical distribution among all parasitic diseases. Endemic in tropical and subtropical regions, the disease is one of the major neglected diseases threatening populations in developing countries. At present, schistosomiasis is prevalent in 76 countries and regions around the world, with a population of about 779 million and about 207 million infected people. [0003] So far there is no effective anti-schistosomiasis vaccine, chemotherapy is the ...

Claims

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Application Information

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IPC IPC(8): C07D209/88C07D401/06C07D209/86A61K31/403A61K31/454A61P33/10A61P33/12
CPCC07D209/86C07D209/88C07D401/06Y02A50/30
Inventor 段李平李军王味思张文宝魏玉芬陶奕刘欢元薛剑郭宝平张皓冰王慧
Owner STATION OF VIRUS PREVENTION & CONTROL CHINA DISEASES PREVENTION & CONTROL CENT
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