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Synthesis of iminosugar-Containing KRN7000 Analogues

Chinese Journal of Chemistry 2017年第6期35卷 1001-1008页

作者： LeiZhang Xin-Shan Ye State Key Laboratory of Natural and Biomimetic Drugs School of Pharmaceutical Sciences Peking University Xue Yuan Road No. 38 Beijing 100191 China

Three new iminosugar-containing KRN7000 （also referred to as α-GalCer） analogues were designed and syn- thesized. In the design, the galactose moiety of KRN7000 was replaced by iminosugars and the iminosugar struc- tures were connected with ceramide in different manners with a C-glycosidic bond instead of the O-glycosidic bond. To our knowledge, this is the first report in which iminosugars are incorporated in KRN7000 structure modifica- tions. The synthetic compounds were evaluated for their ability to stimulate cytokine release. The results may benefit better understanding of structure-activity relationships and facilitate future design of more KRNT000 derivatives.

关键词： KRN7000 analogue glycolipid a-GalCer iminosugar synthesis

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Some iminosugars:Their Syntheses and Biological Activities

Some Iminosugars:Their Syntheses and Biological Activities

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中国化学会第26届学术年会化学生物分会场

作者： Xin-Shan Ye The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd #38, Beijing 100083, China

iminosugars, also called the "sugar-shaped alkaloids", are carbohydrate analogues in which the ring oxygen has been replaced by nitrogen and are found to be widespread in the plants and microorganisms. They are frequently found to be potent inhibitors of many carbohydrate-processing enzymes such as glycosidases involved in important biological systems.[1,2] These unique molecules promise a new generation of iminosugar-based medicines in a wide range of diseases such as diabetes, viral infections, tumor metastasis, and lysosomal storage disorders.[3] However, these iminosugar derivatives as immunosuppressive agents are less explored and little is known about their inhibition effects on immune system responses. We describe herein the synthesis of some iminosugar derivatives and their effects on the secretion of IL-4 and IFN-gamma from the mouse splenocytes.[4,5] Our results demonstrate that synthetic iminosugars may hold the potential as new immunosuppressive agents. On the other hand, some iminosugar derivatives possessing potential anti-tumor activities will be also discussed.[6]

关键词： iminosugar carbohydrate-based drug synthesis

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