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Tetrahydro-beta-carbolinyl-3- formyl-diethylenetriamino-beta-cyclodextrin copper complex, and preparation, antithrombotic action and application thereof

A technology of diethylenetriamine and cyclodextrin, which is used in the preparation of medicines as antithrombotic agents, in the field of modification and complexation of β-cyclodextrin, can solve the problems of limited application of water solubility, and improve the antithrombotic effect. The effect of thrombosis

Inactive Publication Date: 2015-05-27
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the extremely low water solubility of carboline carboxylic acid limits its application as an antithrombotic agent.

Method used

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  • Tetrahydro-beta-carbolinyl-3- formyl-diethylenetriamino-beta-cyclodextrin copper complex, and preparation, antithrombotic action and application thereof
  • Tetrahydro-beta-carbolinyl-3- formyl-diethylenetriamino-beta-cyclodextrin copper complex, and preparation, antithrombotic action and application thereof
  • Tetrahydro-beta-carbolinyl-3- formyl-diethylenetriamino-beta-cyclodextrin copper complex, and preparation, antithrombotic action and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 prepares 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1)

[0023] Add 0.1 mL of concentrated sulfuric acid dropwise to 200.0 mL of water, add 5.000 g of tryptophan (24.5 mmol), and after the tryptophan is completely dissolved, add dropwise 5.0 mL of formaldehyde. After 6 hours of reaction, the reaction was terminated, and the pH value of the system was adjusted to 6 with concentrated ammonia water, resulting in a large amount of white precipitate. The reaction mixture was frozen in a refrigerator at 4°C for several hours, and filtered to obtain 3.985 g of the title compound, with a yield of 75%. ESI / MS(m / e): 217[M+H] + .

Embodiment 2

[0024] Embodiment 2 prepares N-Boc-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2)

[0025] 1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid (5.000g, 23.1mmol) was suspended in 50.0mL DMF, and Boc was added under ice-cooling 2 O (6.545g, 30.1mmol), triethylamine was added dropwise to adjust the pH of the reaction system to 10. After the reaction is complete, dry DMF, dissolve the product mixture in ethyl acetate, wash three times with 5% potassium bisulfate, and wash twice with saturated NaCl solution until the pH of the ester layer is neutral, and anhydrous Na 2 SO 4 Dry the ester layer. After the desiccant was filtered off, the ethyl acetate was spin-dried, and the pale yellow solid was washed with a small amount of chloroform until it became colorless to obtain 4.308 g of the title compound, with a yield of 59%. ESI / MS(m / e): 317[M+H] + .

Embodiment 3

[0026] Embodiment 3 prepares 4-toluenesulfonic anhydride (3)

[0027] TsCl (8.000g, 42.0mmol) and TsOH·H 2 O (2.000 g, 11 mmol) was dissolved in 50.0 mL of dichloromethane and stirred overnight at room temperature. After the reaction solution was filtered and recrystallized, 4.970 g of the title compound was obtained, with a yield of 62%. ESI / MS(m / e): 327[M+H] + .

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Abstract

The invention discloses complexes formed by 6-[(1,2,3,4-tetrahydro-beta-carbolinyl-3)-formacyl-diethylenetriamino]-6-desoxy-beta-cyclodextrin (formed by connecting tetrahydro-beta-carbolinylcarboxylic acid to cyclodextrin by using diethylenetriamine as a connecting arm) and copper and a preparation method thereof. The invention further discloses favorable in-vivo antithrombotic activity and in-vitro vasodilatation action of the copper complexes. The invention provides excellent candidate compounds for developing medicines with high bioavailability and strong antithrombotic activity.

Description

technical field [0001] The invention relates to an artificially synthesized tetrahydro-β-carboline-3-formyl-diethylenetriamine-β-cyclodextrin copper complex, in particular to the modification and complexation of β-cyclodextrin strategy, the present invention also relates to the preparation method of the complex and its application in the preparation of antithrombotic drugs. Background technique [0002] In recent years, my country's population is aging and the incidence of thrombotic diseases is increasing. Although antithrombotic drugs, including antiplatelet drugs, anticoagulant drugs and thrombolytic drugs, have made great progress in development, application and clinical treatment, the development of safer, more effective and highly bioavailable self-owned brands New antithrombotic drug candidates are still one of the hot spots in the development of new drugs. β-carboline alkaloids are a very important class of indole alkaloids. There are many kinds of these alkaloids...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/48A61K31/437A61K31/30A61P9/08A61P7/02
Inventor 李莉赵明王玉记安然
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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