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Triazole glycolipid derivatives and application thereof to synergically resist drug-resistant bacteria

A derivative, triazole technology, applied in the field of triazole glycolipid derivatives and their synergistic anti-drug-resistant bacteria, can solve problems such as adverse reactions of antibiotics

Active Publication Date: 2015-04-22
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If the dose is too large or the medication time is too long, antibiotics will cause various adverse reactions, some of which are even quite serious.

Method used

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  • Triazole glycolipid derivatives and application thereof to synergically resist drug-resistant bacteria
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  • Triazole glycolipid derivatives and application thereof to synergically resist drug-resistant bacteria

Examples

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preparation example Construction

[0023] In the preparation method provided above, the azide compound (R 1 -N 3 ) can be prepared by classical end group bromination and azide substitution of various acetylated monosaccharides, see Alvarez S.G. & Alvarez, M.T. Synthesis, 1997, 413-414 for specific steps.

[0024] In the presence of NaH and at room temperature, the halogenated alkyne with the corresponding alcohol (R 2 OH) and a halogenated hydrocarbon (reaction medium) for at least 12 hours, followed by steps such as evaporation of the reaction medium, extraction, drying, filtration and concentration to obtain the intermediate

[0025] in anhydrous CuSO 4 In the presence of VcNa, inert gas (gas that does not participate in the reaction, such as nitrogen, etc.), and at room temperature, the azide compound (R 1 -N 3 ) and intermediates React for at least 12 hours, and the reaction product is washed successively, extracted, dried, filtered, concentrated and column chromatographed to obtain a product with...

Embodiment 1

[0028] (1) Synthesis of azidoglucose (compound shown in formula A) protected by all acetyl groups:

[0029]

[0030] Put glucose (3g, 0.017moL) into a 100mL flask, then slowly add Ac 2 O (11.9 mL) and HClO 4 (0.072mL) of the mixed solution, after the dropwise addition, remove the ice bath, react at room temperature, follow the reaction by TLC, until the raw material point disappears (at least about 6 hours), stop the reaction. Wash with ice saturated sodium bicarbonate and sodium chloride solution, extract with dichloromethane, and dry (MgSO 4 ), filtered and concentrated under vacuum to give the crude product (5.85 g, 90%). The obtained crude product was directly carried out to the next reaction without further purification.

[0031] Weigh all acetyl-protected glucose (0.53g, 0.001moL), add 30mL of dichloromethane as a solvent, then add 5mL of 30% HBr / AcOH solution to the system, react at room temperature, follow the reaction by TLC, until the starting material The spo...

Embodiment 2

[0042] Except replacing the n-dodecyl alcohol in the step (2) of Example 1 with n-tetradecyl alcohol, other raw materials used, reagents and steps are similar to those in Example 1, and the compound shown in formula IB can be obtained:

[0043]

[0044] 1 H NMR (400MHz, DMSO) δ8.32(s, 1H), 5.57(d, J=9.3Hz, 1H), 5.44(d, J=5.9Hz, 1H), 5.35(s, 1H), 5.23(d ,J=5.3Hz,1H),4.70(s,1H),4.54(s,2H),3.86–3.74(m,2H),3.50(d,J=6.4Hz,4H),3.48(s,1H) ,3.33–3.25(m,1H),1.30(s,24H),0.91(t,J=6.7Hz,3H).

[0045] 13 C NMR (101MHz, DMSO) δ143.9, 123.0, 87.4, 79.8, 79.2, 78.9, 78.6, 76.9, 71.9, 69.7, 69.5, 63.2, 60.7, 54.8, 48.5, 31.2, 29.1, 29.0, 28.9, 28.7, 25.6, 22.0 ,13.9.

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Abstract

The invention relates to a kind of triazole glycolipid derivatives and application thereof to synergically resist drug-resistant bacteria. The triazole derivatives containing a monosaccharide group are compounds shown as a formula I, or pharmaceutically acceptable salts. The provided triazole derivatives have synergic bacteriostatic effect for conventional antibiotics, help to substantially reduce usage amount of antibiotics when being combined with the conventional antibiotics for usage, and provide an approach for reasonable safe usage of antibiotics. In the formula I, R1 is an acetyl-protected or non-acetyl-protected monosaccharide group, R2 is a C6-C18 linear or branched alkyl, and n is an integer of 1-4.

Description

technical field [0001] The invention relates to a triazole glycolipid derivative and its synergistic anti-drug-resistant bacteria application, in particular to a triazole glycolipid derivative containing a monosaccharide group and its synergistic anti-drug resistance use of bacteria. Background technique [0002] From the late 19th century to the early 20th century, scientists paid great attention to the etiology of diseases, and many pathogenic bacteria began to be discovered. Sulfa has a strong antibacterial effect, and its development has successfully saved countless lives. This is the first drug discovered by humans that can fight pathogenic bacteria, which has epoch-making significance. Subsequently, penicillin was called the most valuable contribution in the history of modern medicine, and was hailed as a major milestone in the history of human medicine. Penicillin and streptomycin have become the pioneers of human beings entering the era of antibiotics. Antibiotics...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/056C07H1/00A61K31/7056A61P31/04A61P31/00A61K31/431A61K31/546
CPCC07H1/00C07H19/056
Inventor 贺晓鹏陈代杰胡习乐李丹程超英董晓景邵雷李忠磊陈国荣
Owner EAST CHINA UNIV OF SCI & TECH
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