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Dihydroxymethyl tetrahydrocarboline-3-formyl-The as well as synthesis, activity and application thereof

A kind of dimethylol, tert-butyldimethylsiloxy technology, applied in the field of biomedicine

Active Publication Date: 2020-10-20
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Similarly, in the past more than ten years, the inventor's team has worked hard to invent drugs with anti-arterial thrombosis

Method used

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  • Dihydroxymethyl tetrahydrocarboline-3-formyl-The as well as synthesis, activity and application thereof
  • Dihydroxymethyl tetrahydrocarboline-3-formyl-The as well as synthesis, activity and application thereof
  • Dihydroxymethyl tetrahydrocarboline-3-formyl-The as well as synthesis, activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 Preparation of (3S)-1,1-dimethylol-tetrahydro-β-carboline-3-carboxylic acid (1)

[0018] Add 3.06g (15mmol) of L-tryptophan to 50mL of distilled water, stir well to make it suspend. Under the condition of ice bath, concentrated sulfuric acid was slowly added dropwise to the suspension until the L-tryptophan was completely dissolved. Then add 1.62g (18mmol) 1,3-dihydroxyacetone to the solution, and react at room temperature for 84 hours. TLC showed the disappearance of L-tryptophan (ethyl acetate / water / glacial acetic acid, 4 / 1 / 1). Filtration and washing of the filter cake with ice water gave 2.90 g (70%) of the title compound as a yellow powder.

Embodiment 2

[0019] Example 2 Preparation of (3S)-1,1-dimethylol-tetrahydro-β-carboline-3-carboxylic acid methyl ester (2)

[0020] Slowly add 4.7mL of thionyl chloride dropwise to 50mL of methanol in an ice bath, stir for 30 minutes, then add 5.0g (18mmol) of (3S)-1,1-dimethylol-tetrahydro-β-carboline- 3-Carboxylic acid (1). Stir until compound 1 is completely dissolved. Thereafter, it was stirred at room temperature for 10 hours. TLC showed disappearance of compound 1 (dichloromethane / methanol, 20:1). The reaction mixture was concentrated under reduced pressure, and the residue was triturated with ethyl acetate. The supernatant was removed, and the residue was triturated with ethyl acetate. The resulting tan solid was dissolved in 100 mL of ethyl acetate. The solution was successively washed with saturated NaHCO 3 aqueous solution (30 mL×3), washed with saturated NaCl aqueous solution (30 mL×3), and the ethyl acetate layer was dried over anhydrous sodium sulfate for 12 hours. Filt...

Embodiment 3

[0021] Example 3 Preparation of (3S)-1,1-bis(tert-butyldimethylsilyloxy)methyl-tetrahydro-β-carboline-3-carboxylic acid methyl ester (3)

[0022] Add 4.35 g (15 mmol) of 1,1-dimethylol-β-carboline-3-carboxylic acid methyl ester (2) to 50 mL of anhydrous N,N-dimethylformamide (DMF). Stir until compound 2 is completely dissolved. Thereafter, 3.66 g (64.8 mmol) of imidazole was added to the solution under ice cooling. Stir until the imidazole is completely dissolved. Thereafter, 6.79 g (45 mmol) of tert-butyldimethylsilyl chloride (TBDMSCl) was added to the solution. The reaction mixture was stirred at room temperature for 6 hours. TLC showed that compound 2 disappeared (petroleum ether / ethyl acetate, 20 / 1). The reaction mixture was concentrated under reduced pressure, and the residue was diluted with 100 mL of saturated NaCl aqueous solution. The resulting solution was extracted with ethyl acetate (60mL×3), and the ethyl acetate layer was washed with saturated NaHCO 3 aque...

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Abstract

The invention discloses (3S)-1,1-dihydroxymethyl-tetrahydro-beta-carboline-3-formyl-The, a preparation method of the compound, and anti-arterial thrombosis activity of the compound. The invention further discloses an application of the compound in the preparation of antithrombotic drugs.

Description

technical field [0001] The present invention relates to (3S)-1,1-dimethylol-tetrahydro-β-carboline-3-formyl-The with the following structure, its preparation method, and its antithrombotic activity. Therefore, the present invention relates to the application of the compound in the preparation of antithrombotic drugs. The invention belongs to the field of biomedicine. [0002] Background technique [0003] Both in developed and developing countries, the mortality and morbidity of thrombosis are increasing year by year. In my country, arterial thrombosis has become the first fatal thrombotic disease. It is well known that almost all malignant tumors can be transferred through thrombus. A large number of clinical studies have shown that arterial thrombosis accounts for more than 80% of malignant tumor cases. Invention of drugs with anti-thrombotic activity has always been one of the frontiers in the field of biomedicine. Similarly, in the past ten years or so, the inven...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61P7/02
CPCC07D471/04A61P7/02Y02P20/55
Inventor 赵明彭师奇张筱宜郤思远
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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