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Indole-quinolizine-6-methylol-glucuronate, preparation, activity and application thereof

A technology of furan glucuronate and hydroxymethyl, which is applied in the field of indoquinazine-6-hydroxymethyl-glucuronate, its preparation, activity and application, and can solve the problem of poor prognosis and deterioration of tumor patients The prognosis of cancer patients and other issues

Active Publication Date: 2018-02-13
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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  • Indole-quinolizine-6-methylol-glucuronate, preparation, activity and application thereof
  • Indole-quinolizine-6-methylol-glucuronate, preparation, activity and application thereof
  • Indole-quinolizine-6-methylol-glucuronate, preparation, activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1 prepares L-tryptophan methyl ester (1)

[0021] Add 3.8mL (50.0mmol) of thionyl chloride dropwise to 50mL of anhydrous methanol in an ice bath, and the dropwise addition is completed in 30 minutes, then add 9.20g (42.0mmol) of L-tryptophan in batches, and stir at room temperature for 24 hours. TLC monitored disappearance of starting material. The reaction mixture was concentrated to dryness under reduced pressure, and the residue was crystallized from methanol-ether to obtain 10.56 g (92%) of the title compound as a colorless solid.

Embodiment 2

[0022] Example 2 Preparation of (3S)-1-(2,2-dimethoxyethyl)-2,3,4,9-tetrahydro-β-carboline carboxylic acid methyl ester (2)

[0023] Dissolve 6.00g (23.5mmol) of L-tryptophan methyl ester hydrochloride in 30mL of methanol, add 6mL of trifluoroacetic acid, stir for 30 minutes, then add 4.8mL (29.3mmol) of 1,1,3,3-tetramethoxy propane. The temperature was raised to 80° C. for 10 hours under stirring, and the spots of raw materials disappeared as monitored by TLC. The reaction solution was cooled to room temperature, and saturated NaHCO was added dropwise 3 The aqueous solution was adjusted to pH 7. Concentrated under reduced pressure, the residue was extracted with 100mL dichloromethane, anhydrous Na 2 SO 4 dry. After filtration, the filtrate was concentrated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether: acetone = 2:1) to obtain 2.47 g (33%) of the title compound as a yellow oil. ESI-MS(m / e):319[M+H] ...

Embodiment 3

[0024] Example 3 Preparation of (3S)-1-(2,2-dimethoxyethyl)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (3)

[0025] Add 0.45g (11.8mmol) LiAlH in batches to 25mL of anhydrous tetrahydrofuran under stirring 4 , and stirred for 0.5 h. It was slowly dropped to 2.47g (7.8mmol) of (3S)-1-(2,2-dimethoxyethyl)-2,3,4,9-tetrahydro-β-carbolinecarboxylic acid methyl ester without In tetrahydrofuran water, the temperature was raised to 40° C. for 3 hours, and the starting point disappeared as monitored by TLC. The reaction solution was cooled to room temperature, and 0.5 mL of 15% NaOH aqueous solution was added to quench the reaction. The aluminum salt was removed by filtration, the filtrate was concentrated to dryness under reduced pressure, and the residue was triturated with ether to obtain 1.10 g (49%) of the title compound as a colorless solid. ESI-MS(m / e):291[M+H] + .

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Abstract

The invention provides (6S)-3-acetyl base-6-methylol-4,6,7,12-tetrahydrofuran-4-oxyindole[2,3-alpha]quinolizine-alph-D-furan glucuronate, 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-glucuronate 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-6-hydroxymethyl-4,6,7,12-tetrahydro-4-oxindole[2,3-α]quinazine-α-D-glucofuran Uroxylate, referred to as ATIQ-TPC, relates to its preparation method, relates to its anti-tumor activity on the mouse S180 transplanted sarcoma model, relates to its anti-tumor metastasis activity on the mouse Lewis lung cancer metastasis model, and relates to it The anti-inflammatory effect on the mouse ear swelling model is further related to its antithrombotic effect on the rat common carotid artery-external jugular vein bypass silk method antithrombotic model. The present invention thus relates to (6S)-3-acetyl-4-oxo-4,6,7,12-tetrahydroindolo[2,3-α]quinazine-6-hydroxymethyl- Application of glucuronic acid ester 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 biomedicine. Background technique [0002] Ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H7/033C07H1/00A61P35/00A61P35/04A61P29/00A61P7/02
CPCC07H1/00C07H7/033
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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