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Dioxane-modified tetrahydrocarboline-3-formyl-The-HGE as well as preparation, antithrombotic activity and application thereof

A technology of dioxane and carboline, applied in the preparation of anti-arterial thrombosis drugs, in the field of arterial thrombosis activity, can solve problems such as no substantial progress

Active Publication Date: 2021-06-04
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, no substantive progress has been made

Method used

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  • Dioxane-modified tetrahydrocarboline-3-formyl-The-HGE as well as preparation, antithrombotic activity and application thereof
  • Dioxane-modified tetrahydrocarboline-3-formyl-The-HGE as well as preparation, antithrombotic activity and application thereof
  • Dioxane-modified tetrahydrocarboline-3-formyl-The-HGE as well as preparation, antithrombotic activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 Preparation of (3S)-1,1-dimethylol-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (1)

[0022] Add 2g (7.2mmol) L-tryptophan benzyl ester to 10mL of dichloromethane, stir well to dissolve it. Under the condition of ice bath, slowly drop 1mL trifluoroacetic acid into the solution. Then add 0.78g (8.6mmol) 1,3-dihydroxyacetone to the solution, and react at room temperature for 7 hours. TLC showed the disappearance of L-tryptophan benzyl ester (dichloromethane / methanol: 30:1). Under ice bath conditions, add 50mL saturated NaHCO to the solution 3 solution, stirred well, then left the dichloromethane layer, and then washed with saturated NaHCO 3 solution (30mL×3), washed with saturated NaCl solution (30mL×3), and the dichloromethane layer was dried over anhydrous sodium sulfate for 12 hours. Filtration and concentration of the filtrate under reduced pressure afforded 2.03 g (77%) of the title compound as a yellow powder. ESI-MS(m / e):367[M+H] + .

Embodiment 2

[0023] Example 2 Preparation of 3S-1-(1,1-dimethyl-1,3-dioxane-6-spiroyl)-1,2,3,4-tetrahydro-β-carboline-3- Benzyl carboxylate (2)

[0024] Add 0.2 g (0.55 mmol) (3S)-1,1-dimethylol-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (1) to 5 mL of anhydrous acetone. Under ice bath conditions, 100 μL of concentrated sulfuric acid was added thereto, and then stirred at room temperature for 3 hours. TLC showed that compound 1 disappeared (petroleum ether / ethyl acetate, 4:1). In an ice bath, with saturated NaHCO 3 The pH value of the reaction solution was adjusted to 7, the obtained solution was concentrated under reduced pressure to remove acetone, the residual solution was extracted and washed with ethyl acetate three times, and the ethyl acetate layer was washed with saturated NaCl solution until neutral. The ethyl acetate layer was dried over anhydrous sodium sulfate for 12 hours. After filtration, the filtrate was concentrated under reduced pressure to obtain a tan sol...

Embodiment 3

[0025] Example 3 Preparation of 3S-1-(1,1-dimethyl-1,3-dioxane-6-spiroyl)-1,2,3,4-tetrahydro-β-carboline-3- Carboxylic acid (3)

[0026] Add 0.20g (0.5mmol) 3S-1-(1,1-dimethyl-1,3-dioxane-6-spiroyl)-1,2,3,4-tetrahydro- β-carboline-3-carboxylate benzyl ester (2) and 0.02 g Pd / C. Stir and pass hydrogen for 12h, TLC showed that compound 2 disappeared (petroleum ether / ethyl acetate, 4:1). Palladium on carbon (Pd / C) was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was triturated with ether to afford 0.14 g (90%) of the title compound as a colorless solid. ESI-MS(m / e):317[M+H] + .

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Abstract

The invention discloses 3S-1-(1,1-dimethyl-1,3-dioxane-6-spiroyl)-1,2,3,4-tetrahydro-beta-carboline-3-formyl-The-His-Gly-Glu as shown in the following formula, as well as a preparation method and an anti-arterial thrombosis activity thereof. Therefore, the invention discloses application of the compound in preparation of anti-arterial thrombosis drugs.

Description

technical field [0001] The present invention relates to 3S-1-(1,1-dimethyl-1,3-dioxane-6-spiroyl)-1,2,3,4-tetrahydro-β-carboline-3-methan Acyl-The-His-Gly-Glu compound, its preparation process, its arterial thrombosis activity. Therefore the present invention relates to its application in the preparation of anti-arterial thrombosis drugs. The invention belongs to the field of biomedicine. [0002] Background technique [0003] Arterial embolism has become one of the diseases with high morbidity and mortality. Arterial thrombosis is responsible for transient ischemic attacks, acute coronary syndromes, myocardial infarction and atrial fibrillation. Coronary artery disease is present in 18%-47% of patients with atrial fibrillation, and about 20% of patients with atrial fibrillation associated with coronary artery disease receive percutaneous coronary intervention. Arterial thrombosis is also responsible for arterial thrombosis and unstable angina after artificial heart v...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/08C07K1/02A61K38/08A61P7/02
CPCC07K7/06A61P7/02A61K38/00
Inventor 赵明彭师奇郤思远
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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