Indoloquinazine-6-formyl-3-glucosamine, its preparation, activity and application

A technology of glucosamine and quinozine, which is applied in the field of indoloquinazine-6-formyl-3-glucosamine, its preparation, activity and application, and can solve the problems of worsening prognosis of tumor patients and poor prognosis of tumor patients

Active Publication Date: 2020-01-17
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Thrombus and inflammation are complicated by tumor patients, which makes the prognosis of tumor patients poor
In addition, tumor metastasis worsens the prognosis of tumor patients

Method used

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  • Indoloquinazine-6-formyl-3-glucosamine, its preparation, activity and application
  • Indoloquinazine-6-formyl-3-glucosamine, its preparation, activity and application
  • Indoloquinazine-6-formyl-3-glucosamine, its preparation, activity and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1 prepares L-tryptophan benzyl ester (1)

[0020] 20.40 g (100.0 mmol) of L-tryptophan, 13.00 g (120 mmol) of benzyl alcohol and 40.60 g (120.0 mmol) of polyphosphoric acid were reacted at 80° C. for 72 hours. The reaction solution was lowered to room temperature, 30 mL of anhydrous ether was added, and stirred for 2 hours to precipitate a colorless solid, which was filtered. The filter cake was washed repeatedly with ether to obtain 35.40 g (90%) of the title compound as a colorless solid.

Embodiment 2

[0021] Example 2 Preparation of (3S)-1-(2,2-dimethoxyethyl)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (2)

[0022] Add 8mL (48.8mmol) 1,1,3,3-tetramethoxypropane and 9mL trifluoroacetic acid to 123mL dichloromethane successively under stirring in an ice bath, and activate for 40 minutes. Then add 10.00g (25.5mmol) L-tryptophan benzyl phosphate, stir at room temperature for 120 hours, the reaction is over. Slowly add saturated Na with stirring in an ice bath 2 CO 3 aqueous solution, stirred vigorously until the pH of the aqueous layer was 7, and the separated dichloromethane layer was sequentially washed with 5% NaHCO 3 aqueous solution and saturated NaCl aqueous solution. Dichloromethane layer with anhydrous Na 2 SO 4 After drying and filtering, the filtrate was concentrated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether: acetone = 3:1) to obtain 2.21 g (22%) of the title compound as...

Embodiment 3

[0023] Example 3 Preparation of (3S)-1-(2,2-dimethoxyethyl)-2-acetoacetyl-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (3)

[0024] Dissolve 2.93g (7.4mmol) (3S)-1-(2,2-dimethoxyethyl)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester in 50mL Acetone, add 0.9mL diketene and 0.6mL triethylamine under stirring in an ice bath, stir at room temperature for 17 hours, TLC shows that the raw materials completely disappear. Add 2.5 mL of distilled water to the reaction mixture under ice-bath stirring, stir for 1 hour, concentrate under reduced pressure to remove acetone, and extract the residue three times with dichloromethane. The combined dichloromethane layers are sequentially washed with 5% NaHCO 3 aqueous solution and saturated NaCl aqueous solution, and the dichloromethane layer was washed with anhydrous NaCl 2 SO 4 After drying and filtering, the filtrate was concentrated to dryness under reduced pressure and purified by silica gel column chromat...

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Abstract

The invention provides (6S)-3-acetyl base-4-oxo-4,6,7,12-tetraindole-[2,3-alpha]quinolizine-6-formyl-(3-glucosamine), provides a preparation method thereof, discloses the anti-tumor activity thereof in a mice S180 transplanted sarcoma model, discloses the anti-tumor metastasis activity thereof in a mice Lewis lung cancer metastasis model, discloses an anti-inflammation role thereof in a mice ear swelling model, and further discloses an anti-thrombus role thereof in a rat common carotid artery-external jugular vein circulation bypath thread method anti-thrombus model. The invention discloses application of (6S)-3-acetyl base-4-oxo-4,6,7,12-tetraindole-[2,3-alpha]quinolizine-6-formyl-(3-glucosamine) in preparation of anti-tumor drugs, anti-lung cancer metastasis drugs, anti-inflammation drugs and anti-thrombus drugs.

Description

technical field [0001] The present invention relates to (6S)-3-acetyl-4-oxo-4,6,7,12-tetrahydroindolo[2,3-α]quinazine-6-formyl-(3-glucosamine ), referred to as ATIQC-TMTP, related to its preparation method, related to its anti-tumor activity on the mouse S180 transplanted sarcoma model, related to its anti-tumor metastasis activity on the mouse Lewis lung cancer metastasis model, and related to its anti-tumor activity on the mouse Lewis lung cancer metastasis model. The anti-inflammatory effect on the ear swelling model further relates to its antithrombotic effect on the common carotid artery-external jugular vein circulation bypass silk thread method antithrombotic effect in rats. The present invention thus relates to (6S)-3-acetyl-4-oxo-4,6,7,12-tetrahydroindolo[2,3-α]quinazine-6-formyl-(3-amino Glucose) in the preparation of anti-tumor drugs, anti-tumor lung cancer metastasis drugs, anti-inflammatory drugs and antithrombotic drugs. The invention belongs to the field of bi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/26A61P7/02A61P29/00A61P35/00A61P35/04
CPCC07H15/26
Inventor 赵明彭师奇王玉记吴建辉徐昕怡
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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