methyl 6-methoxyamino-4-O-(4-methoxybenzyl)-6-deoxy-α-D-glucopyranoside | 872677-68-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-methoxyamino-4-O-(4-methoxybenzyl)-6-deoxy-α-D-glucopyranoside
• 英文别名: methyl 6-methoxylamino-2,3-di-O-tetradecyl-6-deoxy-α-D-glucopyranoside；(2R,3R,4S,5R,6S)-6-methoxy-2-[(methoxyamino)methyl]-4,5-di(tetradecoxy)oxan-3-ol
• CAS: 872677-68-4
• 化学式: C₃₆H₇₃NO₆
• 分子量: 615.979
• InChiKey: RRHVTAHGFBVUHM-GJXDWMKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  43
• 可旋转键数：
  32
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  78.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-二氢呋喃 、 methyl 6-methoxyamino-4-O-(4-methoxybenzyl)-6-deoxy-α-D-glucopyranoside 在 4-甲基苯磺酸吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 9.0h， 以68%的产率得到methyl 6-deoxy-6-[N-(2'-tetrahydrofuranyl)-N'-methoxyamino]-2,3-di-O-tetradecyl-α-D-glucopyranoside
  参考文献：
  名称：

  脂质的抑制通过氨基和羟氨基单糖刺激人树突状细胞和巨噬细胞的活化。

  摘要：

  DOI：

  10.1002/anie.200604932
• 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 、 sodium cyanoborohydride 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三氟乙酸 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 11.5h， 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

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.
• WO2007/107285
  申请人：——

  公开号：——

  公开（公告）日：——
• LIPID A ANTAGONISTS WITH ANTI-SEPTIC SHOCK, ANTI-INFLAMMATORY, ANTI-ISCHEMIA AND ANALGESIC ACTIVITY
  申请人：Università Degli Studi Di Milano - Bicocca

  公开号：EP1996603B1

  公开（公告）日：2009-07-15
• 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.
• 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