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Dihydroxyltetrahydroisoquinoline-3-formyl amino acids as well as synthesis, antithrombotic effect and application thereof

A kind of technology of tetrahydroisoquinoline and formyl amino acid, applied in the field of biomedicine

Inactive Publication Date: 2013-12-18
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many limitations in the current clinical application of antithrombotic drugs, and finding safe and effective new antithrombotic drugs is one of the hot spots in drug research

Method used

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  • Dihydroxyltetrahydroisoquinoline-3-formyl amino acids as well as synthesis, antithrombotic effect and application thereof
  • Dihydroxyltetrahydroisoquinoline-3-formyl amino acids as well as synthesis, antithrombotic effect and application thereof
  • Dihydroxyltetrahydroisoquinoline-3-formyl amino acids as well as synthesis, antithrombotic effect and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1 Preparation of (3S)-6,7-dihydroxy-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

[0016] 5.0 g (25 mmol) of 3,4-dihydroxy-L-phenylalanine were dissolved in 250 ml of acetone. To the resulting solution was added 6.0 g (30 mmol) of dried anhydrous magnesium sulfate. After stirring for 30 minutes, 25 ml of trifluoroacetic acid was added under ice cooling. The reaction mixture was then stirred at room temperature for 96 h, TLC (dichloromethane / methanol, 1:1) showed the disappearance of 3,4-dihydroxy-L-phenylalanine. The reaction mixture was filtered to remove solid magnesium sulfate. The filtrate was concentrated under reduced pressure on a water pump to remove acetone and trifluoroacetic acid. After the residue was a syrupy liquid, it was dissolved in acetone and continued to concentrate under reduced pressure, repeating 3 times. The residue was added with 200ml of anhydrous diethyl ether, a large amount of colorless solid was precipitated, and...

Embodiment 2

[0017] Example 2 Preparation of (3S)-6,7-dihydroxy-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-formyl-L-Ala-OBzl (2a)

[0018] 616 mg (2.6 mmol) of (3S)-6,7-dihydroxy-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid were dissolved in 3 ml of anhydrous DMF. To the resulting solution was added 324 mg (2.4 mmol) of N-hydroxybenzotriazole. After 10 minutes, a solution of 500 mg (2.2 mmol) dicyclohexylcarbodiimide and 5 ml anhydrous DMF was added under ice cooling to obtain a reaction solution (I). 702 mg (2 mmol) of Tos·Ala-OBzl was dissolved in 5 ml of anhydrous DMF and stirred for 30 minutes to obtain a reaction solution (II). The reaction solution (II) was added to the reaction solution (I) under ice-cooling, and then stirred at room temperature for 12 h. TLC (dichloromethane / methanol, 6:1) showed that Tos·Ala-OBzl disappeared. The reaction mixture was filtered to remove dicyclohexylurea. DMF was purged from the filtrate at room temperature. The residue was ...

Embodiment 3

[0019] Example 3 Preparation of (3S)-6,7-dihydroxy-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-formyl-Gly-OBzl (2b)

[0020] According to the method of Example 2, 616mg (2.6mmol) 3S)-6,7-dihydroxyl-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and 674mg (2 mmol) Tos.Gly-OBzl yielded 250 mg (25%) of the title compound as a colorless powder. ESI-MS(m / e)85[M+H] + .

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Abstract

The invention provides 15 6,7-dibydroxyl-1,1-dibydroxyl-tetrahydroisoquinoline-3-formyl amino acids of a general formula I. In the general formula I, AA is selected from L-Ala, Gly, L-Phe, L-Val, L-Leu, L-Ile, L-Trp, L-Ser, L-Thr, L-Tyr, L-Lys, L-Pro, L-Asp, L-Arg and L-Glu residues. The invention provides preparation methods of amino acids, and further provides the antithrombotic effect thereof on a rat carotid artery / jugular vein bypass intubation antithrombotic model. Therefore, the 15 6,7-dibydroxyl-1,1-dibydroxyl-tetrahydroisoquinoline-3-formyl amino acids of the general formula I has application prospect in clinical antithrombotic agents.

Description

technical field [0001] The present invention relates to 15 kinds of 6,7-dihydroxyl-1,1-dimethyl-tetrahydroisoquinoline-3-formyl amino acids of general formula I (AA in the formula is selected from L-Ala, Gly, L-Phe , L-Val, L-Leu, L-Ile, L-Trp, L-Ser, L-Thr, L-Tyr, L-Lys, L-Pro, L-Asp, L-Arg, and L-Glu residues ), relate to their preparation methods, and further relate to their antithrombotic effect on the antithrombotic model of rat jugular arteriovenous bypass cannulation. Therefore, the present invention relates to 15 kinds of 6,7-dihydroxy-1,1-dimethyl-tetrahydroisoquinoline-3-formyl amino acids of the general formula I, which have application prospects as clinical antithrombotic agents. The invention belongs to the field of biomedicine. [0002] Background technique [0003] The incidence of thrombotic disease ranks first among all kinds of diseases, and it has gradually increased in recent years, seriously threatening human health. Drug treatment of thrombotic di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/078A61K38/05A61P7/02
Inventor 赵明彭师奇吴建辉王玉记赵洵
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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