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C-glycosides type slycolipid compounds and use thereof

A carbon glycoside glycolipid compound technology, applied in the field of carbon glycoside glycolipid compounds

Inactive Publication Date: 2008-02-20
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is very likely to be a vaccine against Lyme disease, however, as a typical class of O-glycoside compounds, it has some drawbacks

Method used

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  • C-glycosides type slycolipid compounds and use thereof
  • C-glycosides type slycolipid compounds and use thereof
  • C-glycosides type slycolipid compounds and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] Add compound 1 (3.55g, 9.49mmol), anhydrous acetonitrile 50mL, trimethylallyl silicon (3.82mL, 28.62mmol) into a 100mL single-necked flask, add BF dropwise with a constant pressure funnel under ice-water bath conditions 3 .Et 2 O (6.3 mL, 47.70 mmol). Stir for seven days (react for about one day and the solution turns orange-red, and the color gradually deepens as time goes on). After the reaction is completed with thin-plate chromatography TLC tracking, the reaction solution is slowly poured into saturated sodium bicarbonate solution and stirred, and there are a lot of bubbles Overflow, extract with 50mL×3 of 1,2-dichloroethane, dry the organic phase with anhydrous sodium sulfate overnight, filter, distill off the solvent under reduced pressure, and finally separate the product by column chromatography, the eluent is petroleum ether: ether =1:1 (v / v), to obtain syrupy compound 2 (1.50g), yield 42.6%.

[0031]

[0032] 0.1716g of compound 2 was dissolve...

Embodiment 2

[0040]

[0041] Dissolve 256.6 mg of compound 3 in 17 ml of anhydrous dichloromethane, add 719.2 mg of stearic acid, 9 mg of DMAP, and stir vigorously. After the solid is fully dissolved, add 79.2 mg of DCCl and react at room temperature for 4 to 5 hours. TLC traces the complete reaction of the substrate , filter under reduced pressure with a funnel, filter out the solid, take the filtrate, and distill under reduced pressure to obtain a fatty solid. Separation by column chromatography and gradient washing with a mixed solution of petroleum ether and ethyl acetate (v / v=5 / 1-4 / 1) as eluents gave compound 6 (141.2 mg) as a fatty solid in a yield of 23.8%.

[0042] h 1 -NMR (500MHz, CDCl3) δ 5.37-5.36 (d, J=3.0Hz, 1H, H-4), 5.22-5.19 (dd, J=5.0, 10.0Hz, 1H, H-2), 5.15-5.12 (m, 2H, H-3, H-2'), 4.31-4.28 (dd, J=3.5, 12.0Hz, 1H, H-6a), 4.26-4.20 (m, 2H, H-1, H-3 'a), 4.16-4.13 (dd, J=6.0, 12.0Hz, H-3'b), 4.08-4.02 (m, 1H, H-5), 4.01-3.98 (dd, J=5.5, 12.0Hz, 1H, h-6b), 2.29-2.23(...

Embodiment 3

[0047] Antitumor activity test

[0048] The inhibition of the proliferation of HeLa cells (purchased from the Cell Bank of Chinese Academy of Sciences) was determined by the MTT method. Cells in the logarithmic growth phase were diluted to 2×104cell / ml and seeded in 96-well plates. After adhering to the wall, culture solutions containing different concentrations of drugs (25, 50, 100ug / ml) were added, and the control group was cultured with equal volumes. For each concentration, 3 parallel holes were cultured in a 37°C, 5% CO2 incubator for 24 hours, then the supernatant was discarded, and 200uL of medium containing MTT (final concentration 0.5g / L) was added to each well, and the culture was continued for 4 hours, and then the supernatant was discarded. Discard the supernatant, add 100uL of DMSO to dissolve the precipitate. The optical density (OD) value was measured with an enzyme-linked immunosorbent assay (Bio-Rad 550) with a wavelength of 492 nm and a reference wavelength...

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Abstract

The invention relates to a carbon-glycoside glycolipid compound and the function thereof. The carbon-glycoside glycolipid compound has the structure as shown in a formula A or a formula B. The synthesized carbon-glycoside glycolipid compound of the invention has prominent anti-tumor activity, and the compound can be used for the preparation of anti-tumor medicines. R1 and R2 in the formula A and the formula B are respectively selected from H or one of the groups as shown in a formula C, and R1 and R2 have at least one group as shown in the formula C; R3 is H or acetyl; R4 and R5 in a formula C are respectively selected from H or one of C1-C6 alkyls; n is 0-15.

Description

technical field [0001] The present invention relates to a carbon glycoside glycolipid compound and its application. Background technique [0002] With the development of glycobiology, glyceroglycolipids have attracted more and more attention in the clinical and pharmaceutical aspects. The exploration of the effects of glycolipids on the human body and the treatment of diseases has achieved practical results. Glycolipids, as important biomolecules in living organisms, have important biological functions such as intercellular interaction and recognition, regulation of cell growth, influence on cancer cell changes, and participation in cell adhesion. Glyceroglycolipid is an important class of glycolipids. Existing research results have confirmed that it has significant pharmacological effects such as anti-tumor, anti-HIV, anti-inflammation, anti-influenza virus, and lowering blood pressure. It is a chemical sugar A hot spot in the field of biological research. Glyceroglycolip...

Claims

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Application Information

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IPC IPC(8): C07D309/10C07H7/00A61K31/351A61P35/00
Inventor 陈国荣宋绍兴沈翼堃
Owner EAST CHINA UNIV OF SCI & TECH
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