methyl 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-glucopyranoside | 637774-19-7

• 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-glucopyranoside
• 英文别名: methyl 4-O-p-methoxybenzyl-2,3-di-O-tetradecanyl-α-D-glucopyranoside；methyl 4-O-p-methoxybenzyl-2,3-di-O-tetradecanyl-alpha-D-glucopyranoside；[(2R,3R,4S,5R,6S)-6-methoxy-3-[(4-methoxyphenyl)methoxy]-4,5-di(tetradecoxy)oxan-2-yl]methanol
• CAS: 637774-19-7
• 化学式: C₄₃H₇₈O₇
• 分子量: 707.088
• InChiKey: BSADEWIULHTSOZ-MHUNNFNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.8
• 重原子数：
  50
• 可旋转键数：
  34
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-glucopyranoside 在 吡啶 、 sodium cyanoborohydride 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.5h， 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
• 作为产物：
  描述：

  methyl 4,6-O-p-methoxybenzylidene-α-D-glucopyranoside 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 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 4.0h， 生成 methyl 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-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

• Saccharide conjugates
  申请人：Demchenko Alexei

  公开号：US09120838B2

  公开（公告）日：2015-09-01

  The invention provides a series of novel Lipid A analogs that are structually simple, synthetically accessible, and capable of blocking the cellular receptor within the signal transduction pathway. The novel Lipid A analogs can include a monosaccharide core with hydrophobic side chains and amino acid ionic motif. The invention further provides methods of using the compounds and compositions thereof in various therapeutic methods.

  这项发明提供了一系列新颖的脂多糖A类似物，这些类似物在结构上简单，易于合成，并能够阻断信号转导途径内的细胞受体。这些新颖的脂多糖A类似物可以包括一个单糖核心，带有疏水侧链和氨基酸离子基序。该发明还提供了在各种治疗方法中使用这些化合物及其组合物的方法。
• Modulators Of The GPR119 Receptor And The Treatment Of Disorders Related Thereto
  申请人：Jones Robert M.

  公开号：US20140066369A1

  公开（公告）日：2014-03-06

  The present invention relates to compounds of Formula I and pharmaceutically acceptable salts, solvates, and hydrates thereof, that are useful as single pharmaceutical agents or in combination with one or more additional pharmaceutical agents, such as, a DPP-IV inhibitor, a biguanide, an alpha-glucosidase inhibitor, an insulin analogue, a sulfonylurea, an SGLT2 inhibitor, a meglitinide, a thiazolidinedione, or an anti-diabetic peptide analogue, in the treatment of for example, a disorder selected from: a GPR119-receptor-related disorder; a condition ameliorated by increasing a blood incretin level; a condition characterized by low bone mass; a neurological disorder; a metabolic-related disorder; type 2 diabetes; obesity; and complications related thereto.

  本发明涉及式I化合物及其药学上可接受的盐、溶剂和水合物，它们可作为单一药物或与一个或多个其他药物联合使用，例如DPP-IV抑制剂、双胍类药物、α-葡萄糖苷酶抑制剂、胰岛素类似物、磺脲类药物、SGLT2抑制剂、噻唑烷二酮类药物或抗糖尿病肽类似物，用于治疗选择性疾病，例如GPR119受体相关疾病、通过增加血液肠促素水平改善的病症、低骨量的病症、神经系统疾病、代谢相关疾病、2型糖尿病、肥胖及其相关并发症。
• SACCHARIDE CONJUGATES
  申请人：Demchenko Alexei

  公开号：US20140066390A1

  公开（公告）日：2014-03-06

  The invention provides a series of novel Lipid A anlogues that are structually simple, synthetically accessible, and capable of blocking the cellular receptor within the signal transduction pathway. The novel Lipid A anlogues can include a monosaccharide core with hydrophobic side chains and amino acid ionic motif. The invention further provides methods of using the compounds and compositions thereof in various therapeutic methods.

  本发明提供了一系列新颖的脂多糖A类似物，这些类似物结构简单、合成容易，并能够阻断信号转导通路内的细胞受体。这些新颖的脂多糖A类似物可以包括具有疏水侧链和氨基酸离子基团的单糖核心。本发明还提供了使用这些化合物及其组合物进行各种治疗方法的方法。
• 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