N-(2-hydroxyethyl)-N-{2-(2,2,2-trichloroethoxycarbonyloxy)ethyl}-2,2,2-trichloroethoxymethanamide | 1428739-37-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: N-(2-hydroxyethyl)-N-{2-(2,2,2-trichloroethoxycarbonyloxy)ethyl}-2,2,2-trichloroethoxymethanamide
• CAS: 1428739-37-0
• 化学式: C₁₀H₁₃Cl₆NO₆
• 分子量: 455.934
• InChiKey: ZPSXRGLZWSHRRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  85.3
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  二乙醇胺 、 氯甲酸-2,2,2-三氯乙酯 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 3.0h， 以78%的产率得到N,N-bis(2-hydroxyethyl)-2,2,2-trichloroethoxymethanamide
  参考文献：
  名称：

  Improving the immunostimulatory potency of diethanolamine-containing lipid A mimics

  摘要：

  Lipid A is the active principal of gram negative bacterial lipopolysaccharide (LPS) in the activation of Toll-like receptor 4 (TLR4). Given the important role TLR4 plays in innate immunity and the development of adaptive immune responses, ligands that can modulate TLR4-mediated signaling have great therapeutic potential. Recently, we have reported a series of monophosphorylated lipid A mimics as potential ligands of TLR4, in which a diethanolamine moiety is employed to replace the reducing end (D-glucosamine). In this paper, we describe the synthesis of two further diethanolamine-containing lipid A mimics, 3 and 4, in an effort to mimic more closely the di-phosphate nature of natural lipid A. Both mimic 3, with an additional phosphate on the diethanolamine acyclic scaffold, and mimic 4, with a terminal carboxylic acid moiety as a phosphate bioisostere, serve to increase the potency of the immunostimulatory response induced, as measured by the induction of the cytokines TNF-alpha, IL-6, and IL-1 beta in the human monocytic cell line THP-1. In addition, mechanistic studies involving the known TLR4 antagonist lipid IVa confirm TLR4 as the target of the diethanolamine-containing lipid A mimics. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.024