methyl 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime | 872677-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime
• 英文别名: methyl 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-gluco-hexodialdo-1,5-pyranoside-6-O-methyloxime；N-methoxy-1-[(2R,3R,4S,5R,6S)-6-methoxy-3-[(4-methoxyphenyl)methoxy]-4,5-di(tetradecoxy)oxan-2-yl]methanimine
• CAS: 872677-66-2
• 化学式: C₄₄H₇₉NO₇
• 分子量: 734.114
• InChiKey: HDRNEUOSGDWWMJ-IYFSMEFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  52
• 可旋转键数：
  35
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime 在 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 methyl 6-methoxyamino-4-O-(4-methoxybenzyl)-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of novel lipid A antagonists

  摘要：

  A mimetic of Lipid A with a beta-N(OMe) glycosidic linkage, four linear C-14 hydrophobic chains and without phosphate groups has been prepared together with its beta-O-linked analogue. Both these molecules were active in inhibiting the inflammatory action of Escherichia coli lipid A on MT2 macrophages in a dose-dependent manner, while they were completely devoid of inflammatory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.047
• 作为产物：
  描述：

  methyl 4,6-O-p-methoxybenzylidene-α-D-glucopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 methyl 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime
  参考文献：
  名称：

  Synthesis and biological evaluation of novel lipid A antagonists

  摘要：

  A mimetic of Lipid A with a beta-N(OMe) glycosidic linkage, four linear C-14 hydrophobic chains and without phosphate groups has been prepared together with its beta-O-linked analogue. Both these molecules were active in inhibiting the inflammatory action of Escherichia coli lipid A on MT2 macrophages in a dose-dependent manner, while they were completely devoid of inflammatory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.047

文献信息

• Glycolipids and Benzylammonium Lipids as Novel Antisepsis Agents: Synthesis and Biological Characterization
  作者：Matteo Piazza、Clara Rossini、Silvia Della Fiorentina、Chiara Pozzi、Francesca Comelli、Isabella Bettoni、Paola Fusi、Barbara Costa、Francesco Peri

  DOI：10.1021/jm801333m

  日期：2009.2.26

  New glycolipids and a benzylammonium lipid were rationally designed by varying the chemical structure of a D-glucose-derived hit compound active as lipid A antagonist. We report the synthesis of these compounds, their in vitro activity as lipid A antagonists on HEK cells, and the capacity to inhibit LPS-induced septic shock in vivo. The lack of toxicity and the good in vivo activity suggest the use of some compounds of the panel as hits for antisepsis drug development.
• Inhibition of Lipid A Stimulated Activation of Human Dendritic Cells and Macrophages by Amino and Hydroxylamino Monosaccharides
  作者：Francesco Peri、Francesca Granucci、Barbara Costa、Ivan Zanoni、Chiara Marinzi、Francesco Nicotra

  DOI：10.1002/anie.200604932

  日期：2007.4.27
• WO2007/107285
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and biological evaluation of novel lipid A antagonists
  作者：Francesco Peri、Chiara Marinzi、Marek Barath、Francesca Granucci、Matteo Urbano、Francesco Nicotra

  DOI：10.1016/j.bmc.2005.08.047

  日期：2006.1

  A mimetic of Lipid A with a beta-N(OMe) glycosidic linkage, four linear C-14 hydrophobic chains and without phosphate groups has been prepared together with its beta-O-linked analogue. Both these molecules were active in inhibiting the inflammatory action of Escherichia coli lipid A on MT2 macrophages in a dose-dependent manner, while they were completely devoid of inflammatory activity. (c) 2005 Elsevier Ltd. All rights reserved.