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Amide ethyoxyl-beta-D-glucoside compound and preparation method and application thereof

A technology of glucoside and ethoxy, which is applied in the field of pharmaceutical compounds to achieve the effect of simple steps and high yield

Inactive Publication Date: 2016-03-23
SHANGHAI SEVENTH PEOPLES HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, there are no reports on the synthesis and related activities of amidoethoxy-β-D-glucoside compounds

Method used

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  • Amide ethyoxyl-beta-D-glucoside compound and preparation method and application thereof

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Experimental program
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Embodiment 1

[0033] Embodiment 1 The preparation of preferred target compound 1a-e of the present invention

[0034] (1) Synthesis of 1-azidoethoxy-2,3,4,6-tetra-O-acetyl-β-D-glucoside (Compound 3)

[0035] Compound 2 (5g, 12.8mmol), azide ethanol (2.22g, 25.6mmol), molecular sieves (5g) and dichloromethane (30ml) were placed in a 100ml eggplant-shaped flask, and after stirring for 1 hour under argon protection, Cool to 0°C, slowly add boron trifluoride diethyl ether (6.47ml, 51.2mmol) dropwise, and stir at room temperature for 2 hours. TLC (petroleum ether: ethyl acetate=2:1, R f =0.45) detection, the reaction is complete. Dichloromethane (200 ml) was added to the reaction solution, and the mixture was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, respectively. The organic layer was dried over anhydrous sodium sulfate and concentrated. Purification by silica gel column chromatography (petroleum ether: ethyl acetate = 4:1) gave a white solid ...

Embodiment 2

[0046] Embodiment 2 Pharmacological experiments of preferred target compounds 1a-e of the present invention

[0047] (1) Experimental materials

[0048] 1. Test sample

[0049] After the target compounds were dissolved in DMSO (Merck), PBS (–) was added to make a 1000 μg / ml solution or a homogeneous suspension, and then diluted with DMSO-containing PBS (–).

[0050] 2. Cell lines

[0051] Human non-small cell lung cancer cells (H460), human liver cancer cells (HEP3B).

[0052] 3. Other materials and main instruments

[0053] Culture medium: RPMI1640 + 15% NBS + double antibody; thiazolium blue (MTT): purchased from Sigma Company (St.Louis, MO, USA); other reagents were domestic analytical grade. Fully automatic microplate reader WellscanMK-2 (Labsystems company), CO 2 Constant temperature incubator (Japan Sanyo Company), imported 96-well culture plate, etc.

[0054] (2) Experimental method

[0055] Both of the above two cell lines were cultured in DMEM medium containing...

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PUM

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Abstract

The invention relates to an amide ethyoxyl-beta-D-glucoside compound and a preparation method and application of the amide ethyoxyl-beta-D-glucoside compound. A structural general formula of the amide ethyoxyl-beta-D-glucoside compound is as shown in formula I in the description, wherein R is selected from straight-chain alkyl. According to the amide ethyoxyl-beta-D-glucoside compound and the preparation method and the application of the amide ethyoxyl-beta-D-glucoside compound, disclosed by the invention, the amide ethyoxyl-beta-D-glucoside compound which is as shown in the formula I is synthesized for the first time, and obvious inhibitory activity of the amide ethyoxyl-beta-D-glucoside compound on two types of tumor cells: a human non-small cell lung cancer cell H460 and a human hepatoma carcinoma cell HEP3B is verified, so that the amide ethyoxyl-beta-D-glucoside compound can be used for preparing drugs for resisting tumors; meanwhile, the steps of a synthetic route of the amide ethyoxyl-beta-D-glucoside compound are simple, and the achieving rate is high.

Description

technical field [0001] The invention relates to the technical field of medical compounds, in particular to an amidoethoxy-β-D-glucoside compound, its preparation method and its application in the preparation of antitumor drugs. Background technique [0002] Tumor is one of the diseases that seriously endanger human health. According to the "Global Cancer Report 2014" released by the World Health Organization (WHO), the incidence of cancer in the world is: 182 people / 100,000 people, and the death rate is: 102 people / 100,000 people The report predicts that global cancer cases will show a rapid growth trend, from 14 million in 2012 to 19 million in 2025 and 24 million in 2035. [0003] Chemotherapy is one of the three major methods of cancer treatment. After years of hard work, some cancers can now be cured by drug chemotherapy. However, the currently used anti-tumor drugs have serious side effects: 1) The selectivity to tumor cells is not strong, and while killing tumor cells...

Claims

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Application Information

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IPC IPC(8): C07H15/04C07H1/00A61K31/7028A61P35/00
CPCC07H1/00C07H15/04
Inventor 张宏俞世冲叶颖夏伟陈伟成孙梦瑶戴晶晶赵金双
Owner SHANGHAI SEVENTH PEOPLES HOSPITAL
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