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Cell sugar transport channel inhibitor

A sugar transport and inhibitor technology, applied in the field of biomedicine, to achieve the effect of inhibiting tumor cell proliferation

Active Publication Date: 2021-07-23
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, development of more validated GLUT-selective inhibitors is needed

Method used

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  • Cell sugar transport channel inhibitor
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  • Cell sugar transport channel inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of GLUT inhibitor (I)-(A-1)-1:

[0042] 1. Synthesis of 4-chloro-6-nitro-7-acetamidobenzo-2-oxa-1,3-oxadiazole (II), the synthetic route is as follows:

[0043] 4-Chloro-7-acetamidobenzo-2-oxa-1,3-oxadiazole (XIV, 678.3 mg, 3.0 mmol) was dissolved in 12 mL of acetic anhydride. With stirring at 0 °C, 4 mL of concentrated nitric acid was slowly added dropwise to the mixture. And after stirring was continued at 0° C. for 3 hours, ice water was added. After stirring for 10 min, it was filtered, and the filter cake was washed 3 times with cold water to obtain 753.3 mg of yellow solid (II), with a yield of 59%. 1 HNMR(600MHz,DMSO-d6):δ11.51(s,1H),8.19(s,1H),2.19(s,3H).

[0044] The reaction formula is:

[0045]

[0046] 2. Synthesis of 4-chloro-6-nitro-7-aminobenzo-2-oxa-1,3-oxadiazole (Ⅲ), the synthetic route is as follows:

[0047] Add Ⅱ (256.6mg, 1.0mmol) to 50%wt.H 2 SO 4 aqueous solution (3 mL), and the mixture was stirred at 100°C for 2 hours. The m...

Embodiment 2

[0066] Synthesis of GLUT inhibitor (I)-(A-2)-1:

[0067] 1, Synthesis of 3-tert-butyldimethylsilyloxybenzoyl chloride (X):

[0068] 3-Hydroxybenzoic acid (VIII, 3.0g, 21.7mmol), tert-butyldimethylsilyl chloride (TBSCl) (7.5g, 50.0mmol) and imidazole (3.4g, 50.0mmol) were dissolved in anhydrous N,N - in dimethylformamide (DMF) (30 mL), stirred at room temperature for 24 h. After the reaction was complete, acetone (150 mL) was added to the reaction mixture, filtered, the filtrate was collected, concentrated under reduced pressure, the resulting residue was dissolved in ethyl acetate (50 mL), washed 3 times with saturated aqueous ammonium chloride, anhydrous sodium sulfate After drying, the solvent was removed under reduced pressure to give a colorless liquid.

[0069] The obtained colorless liquid was dissolved in a mixed solvent of glacial acetic acid (50 mL), tetrahydrofuran (15 mL) and water (15 mL), and stirred at room temperature for 4 h. Ethyl acetate (60 mL) and water ...

Embodiment 3

[0078] Synthesis of GLUT inhibitor (I)-(A-3)-1:

[0079] 1. Synthesis of 3,5-bis(tert-butyldimethylsilyloxy)benzoyl chloride (XIII):

[0080] 3,5-dihydroxybenzoic acid (XI, 3.1 g, 20.1 mmol), tert-butyldimethylsilyl chloride (TBSCl) (10.6 g, 70.4 mmol) and imidazole (4.8 g, 70.4 mmol) were dissolved in anhydrous N,N-dimethylformamide (DMF) (30 mL), stirred at room temperature for 24 h. After the reaction was complete, acetone (150 mL) was added to the reaction mixture, filtered, the filtrate was collected, concentrated under reduced pressure, the resulting residue was dissolved in ethyl acetate (50 mL), washed 3 times with saturated aqueous ammonium chloride, anhydrous sodium sulfate After drying, the solvent was removed under reduced pressure to give a colorless liquid.

[0081] The obtained colorless liquid was dissolved in a mixed solvent of glacial acetic acid (50 mL), tetrahydrofuran (15 mL) and water (15 mL), and stirred at room temperature for 4 h. Ethyl acetate (60 ...

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Abstract

The invention discloses a cell sugar transport channel inhibitor of which the structure is shown as a formula (I). The cell sugar transport channel inhibitor disclosed by the invention can target a cell sugar transport channel, and inhibit tumor cell proliferation by directly blocking a GLUT channel and intake of sugar nutrients by tumors; the invention also relates to an application in preparation of antitumor drugs or a reagent for inhibiting a cell sugar transport channel GLUT.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and relates to a cell sugar transport channel inhibitor that inhibits the sugar nutrient absorption of cells and targets the tumor Warburg effect, wherein the cell sugar transport channel is referred to as GLUT. Background technique [0002] At present, malignant tumors are a serious disease that threatens human life and health. The best strategy to deal with tumors is to inhibit tumor growth without harming normal cells and tissues by targeting tumor-specific biological targets. [0003] There are many targeted anti-tumor methods, the basic principle of which is to use tumor biomarkers that exist specifically in tumor cells or tumor tissues, or that are significantly different from normal cells or normal tissues, and selectively identify and inhibit these biomarkers. To achieve the purpose of treating tumors. Studies have shown that one of the important physiological mechanisms for malignan...

Claims

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Application Information

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IPC IPC(8): C07D271/12A61K31/4245A61P35/00
CPCC07D271/12A61P35/00
Inventor 高清志刘胜男王欣瑜
Owner TIANJIN UNIV
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