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Compound of single sugar cluster and heterozygous sugar cluster, preparation method and applications thereof

A compound and hybrid technology, applied in the field of medicinal chemistry, can solve problems such as unreported activity

Inactive Publication Date: 2012-10-03
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no reports in the prior art of single sugar clusters based on glucose, galactose, mannose, and cellobiose, and hybrid sugar cluster compounds combined with lactose and mannose and their activities.

Method used

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  • Compound of single sugar cluster and heterozygous sugar cluster, preparation method and applications thereof
  • Compound of single sugar cluster and heterozygous sugar cluster, preparation method and applications thereof
  • Compound of single sugar cluster and heterozygous sugar cluster, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] General method for the preparation of single sugar cluster sugar units: sugar donors (pentaacetylglucose, pentaacetylgalactose, octaacetylcellobiose) and 2-benzyloxycarbonylamino 1,3-propanediol (3:1) were dissolved in Water CH 2 Cl 2 (1mmol donor / mL), add BF 3 ·OEt 2 (5 equivalents relative to the donor), stirred at room temperature for 24 hours. Mixture with CH 2 Cl 2 After dilution, wash with saturated aqueous sodium bicarbonate solution and water successively, anhydrous Na 2 SO 4 Dry and evaporate the solvent. The crude product was purified by column chromatography, petroleum ether (60-90°C): acetone 3: 2, to obtain a colorless syrup. Then catalytic hydrogenation (0.4 MPa) with Pd / C (20%) in methanol (0.05 mmol / mL) at room temperature for 6 hours to obtain sugar units for the synthesis of sugar clusters.

[0050] 2-Benzyloxycarbonylamino-1,3-di-O-di-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→4)-2 , 3,6-tri--O-acetyl-β-D-glucopyranosyl]propane (compound ...

Embodiment 2

[0057] General method for the preparation of single sugar clusters: polyacids were dissolved in anhydrous THF (0.1 mmol / mL), cooled to 0°C, and then HOBt (1.5 equivalents per carboxyl group) and DCC (1.5 equivalents per carboxyl group) were added. Stir at 0°C for 0.5 hours, add a THF solution (0.1 mmol / mL) of sugar units (1 equivalent per carboxyl group) to pH = 8-9 with N-methylmorpholine, and add the reaction flask to the mixture at 0 After stirring at room temperature for 2 hours at ℃ for 36 hours, the solvent was evaporated and CH 2 Cl 2 , filtered off the insoluble matter, and the solution was washed successively with 10% citric acid solution, saturated sodium bicarbonate solution and water, anhydrous Na 2 SO 4 Dry and evaporate the solvent. The crude product was purified by column chromatography, petroleum ether (60-90°C): acetone 2:3. A colorless syrup was obtained. Then catalytic hydrogenation (0.4MPa) in methanol (0.05mmol / mL) with Pd / C (20%) at room temperature ...

Embodiment 3

[0068] 2-Benzyloxycarbonylamino-3-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-- O-acetyl-β-D-glucopyranosyl]-1-propanol (compound 16)-octaacetyllactose and 2-benzyloxycarbonylamino 1,3-propanediol (1:1) were dissolved in anhydrous CH 2 Cl 2 (0.5mmol donor / mL), add BF 3 ·OEt 2 (3 equivalents relative to the donor), stirred at room temperature for 6 hours. Mixture with CH 2 Cl 2 After dilution, wash with saturated aqueous sodium bicarbonate solution and water successively, anhydrous Na 2 SO 4 Dry and evaporate the solvent. The crude product was purified by column chromatography, petroleum ether (60-90°C):ethyl acetate 2:3, to obtain a colorless syrup. Yield 30%. 1 H NMR (400MHz, CDCl 3 ): δ=7.34(m, 5H; Ph), 5.35(d, 1H; H-4'), 5.26(d, 2H, PhCH 2 O), 5.17(dd, 1H; H-3), 5.11(dd, 1H; H-2'), 4.95(dd, 1H; H-3'), 4.87(t, 1H; H-2), 4.48 (d, J 1，2 =J 1′，2′ = 8.0Hz, 2H; H-1, H-1'), 4.55, 4.17-4.03 (m, 4H; H-6a, b, H-6a', b'), 3.89-3.59 (m, 8H; H-4, 5 , H-5′...

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Abstract

The invention discloses a compound of a single sugar cluster and a heterozygous sugar cluster, which are shown in formula (I), wherein the definition of a substituent group in the compound of the formula (I) is disclosed in detail in the specification. In addition, the invention also discloses a preparation method and a pharmaceutical composition of the compound. The compound has adhesion resistance and a protecting function on endotoxic shock.

Description

technical field [0001] The present invention relates to the technical field of medicinal chemistry, and more specifically relates to a new class of single sugar clusters and hybrid sugar clusters, their preparation methods and their application in biological research of anti-adhesion and anti-shock drugs. Background technique [0002] Endotoxic Shock (ES) is a systemic critical syndrome characterized by tissue hypoperfusion, hypotension and organ dysfunction caused by endotoxin produced by Gram-negative bacteria. Systemic vascular hyporesponsiveness, extensive endothelial cell activation or injury, disseminated intravascular coagulation and even multiple organ dysfunction are typical pathophysiological changes of ES. Due to the high morbidity and mortality of ES, it has attracted widespread attention. [0003] Endotoxin is composed of lipopolysaccharide (LPS) and protein. Lipopolysaccharide is the main component of the cell membrane surface of Gram-negative bacteria and pl...

Claims

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Application Information

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IPC IPC(8): C07H15/04C07H1/00A61K31/7028A61P7/00A61P31/04A61P29/00
Inventor 李庆李中军尹昭军赵智辉孟祥豹李树春娄清华
Owner PEKING UNIV
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