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(3R,12aS)-3-(4-aminobutyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, and preparation and application thereof

A 3-b, diketone technology, applied in the field of biomedicine, can solve problems such as no effect

Inactive Publication Date: 2016-01-27
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, it does nothing for tumor complications

Method used

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  • (3R,12aS)-3-(4-aminobutyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, and preparation and application thereof
  • (3R,12aS)-3-(4-aminobutyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, and preparation and application thereof
  • (3R,12aS)-3-(4-aminobutyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1 prepares 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1)

[0024] Add 0.4 mL of concentrated sulfuric acid into 800 mL of distilled water, stir evenly, add 10 g of L-Trp, and sonicate to aid dissolution; add 20 mL of formaldehyde solution to the reaction solution, and stir at room temperature for 10 hours. Post-processing: add concentrated ammonia water dropwise to the reaction solution to adjust the pH to 6, let it stand still, a colorless solid precipitates, filter and dry to obtain 11.32 g of the crude product. ESI-MS (m / e): 215 [M-H] - .

Embodiment 2

[0025] Example 2 Preparation of 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (2)

[0026] Add 60mL of methanol to a 250mL reaction flask, add 7mL of thionyl chloride dropwise under ice bath, activate for 30 minutes, add 6.2g of 3S-1,2,3,4-tetrahydro-β-carboline-3- Carboxylic acid (1), stirred at room temperature overnight, TLC showed that the starting material basically disappeared. Post-processing: remove the solvent under reduced pressure, dissolve the residue with 100 mL of ethyl acetate, adjust the pH to 8 with triethylamine, and purify by silica gel column chromatography (CH 2 Cl 2 :CH 3 OH=100:1-20:1), yielding 4.625 g (70%) of methyl 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylate as a colorless solid. ESI-MS(m / e): 231[M+H] + .

Embodiment 3

[0027] Example 3 Preparation of 3S-1,2,3,4-tetrahydro-β-carboline-2-(D-Boc-benzyloxycarbonyllysyl)-3-carboxylic acid methyl ester (3)

[0028]Suspend 1.9g (5.0mmol) D-Boc-Lys(Z) in 20mL of anhydrous tetrahydrofuran, add 0.675g (5.0mmol) HOBt to the solution with stirring at room temperature, add 1.133g (5.5mmol) DCC while stirring in an ice bath , to obtain reaction solution I, stirred under ice bath for 30 minutes; 1.15g (5.0mmol) 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (2) was suspended in In 20 mL of anhydrous tetrahydrofuran, the reaction solution II was obtained; the reaction solution II was added to the reaction solution I, stirred for 1 h under ice bath, and stirred overnight at room temperature. Post-treatment: remove DCU by filtration under reduced pressure, concentrate the filtrate under reduced pressure to remove tetrahydrofuran, dissolve the residue with 150mL ethyl acetate, put the obtained solution in a 250mL separatory funnel, and succes...

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Abstract

The invention relates to a micromolecule mu-PA inhibitor (3R,12aS)-3-(4-aminobutyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione with the structural formula shown in the specification, relates to a preparation method of the compound and application of the compound to inhibit tumor invasion and migration, resist coagulation and diminish inflammation as the mu-PA inhibitor. The invention belongs to the field of biological medicine.

Description

technical field [0001] The present invention relates to the small molecule u-PA inhibitor (3S, 6'R)-tetrahydrocarboline [2, 3-b] and [3', 4'-b]-6'-( 1-aminobutyl-4-yl)-piperazine-2', 5'-dione, relates to its preparation method and its application as u-PA inhibitor in inhibiting tumor invasion and migration, anti-inflammation and anti-thrombosis. The invention belongs to the field of biomedicine. [0002] Background technique [0003] The plasminogen activation system consists of plasminogen activators (Pas), plasminogen activation inhibitors (PAIs) and extracellular plasminogen activator receptors (PAR). The plasminogen activation system is involved in a series of processes such as cell migration, angiogenesis, wound healing, embryonic development, tumor cell spread and metastasis. There are mainly two plasminogen activators in mammals, tissue plasminogen activator (t-PA) and urokinase plasminogen activator (u-PA). [0004] Urokinase-type plasminogen activator (u-PA) i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14A61P35/04A61P35/00A61P29/00A61P7/02
Inventor 彭师奇赵明王玉记吴建辉王枫
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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