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Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000.

作者信息

Leung Leo, Tomassi Cyrille, Van Beneden Katrien, Decruy Tine, Elewaut Dirk, Elliott Tim, Al-Shamkhani Aymen, Ottensmeier Christian, Van Calenbergh Serge, Werner Joern, Williams Tony, Linclau Bruno

机构信息

School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK.

出版信息

Org Lett. 2008 Oct 16;10(20):4433-6. doi: 10.1021/ol801663m. Epub 2008 Sep 18.

DOI:10.1021/ol801663m
PMID:18798635
Abstract

The synthesis of 4-deoxy-4,4-difluoro-KRN7000 starting from phytosphingosine is described. Key steps include a regioselective benzylation of azidophytosphingosine and a deoxofluor-mediated fluorination of the corresponding 4-ketone. This fluorination failed completely when the adjacent 3-OH was protected as benzyl ether but proceeded well when a benzoyl group was used. The biological evaluation reveals a bias toward Th1 cytokine induction upon Natural Killer T cell activation.

摘要

相似文献

1
Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000.
Org Lett. 2008 Oct 16;10(20):4433-6. doi: 10.1021/ol801663m. Epub 2008 Sep 18.
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The synthesis and in vivo evaluation of 2',2'-difluoro KRN7000.2',2'-二氟KRN7000的合成及体内评价
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RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage: their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines.RCAI-17、22、24 - 26、29、31、34 - 36、38 - 40以及88，具有磺酰胺连接的KRN7000类似物：它们的合成及其对小鼠自然杀伤T细胞产生Th2偏向性细胞因子的生物活性。
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Effects of lipid chain lengths in alpha-galactosylceramides on cytokine release by natural killer T cells.α-半乳糖神经酰胺中脂链长度对自然杀伤T细胞细胞因子释放的影响。
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3-fluoro- and 3,3-difluoro-3,4-dideoxy-KRN7000 analogues as new potent immunostimulator agents: total synthesis and biological evaluation in human invariant natural killer T cells and mice.3-氟-和 3,3-二氟-3,4-二去氧-KRN7000 类似物作为新型有效的免疫刺激剂：在人不变自然杀伤 T 细胞和小鼠中的全合成和生物学评价。
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Synthesis and biological evaluation of alpha-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3).α-半乳糖神经酰胺（KRN7000）和异球三己糖神经酰胺（iGb3）的合成及生物学评价
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