(3R)-3-hexoxytetradecanoic acid | 1092962-71-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R)-3-hexoxytetradecanoic acid
• CAS: 1092962-71-4
• 化学式: C₂₀H₄₀O₃
• 分子量: 328.536
• InChiKey: QMAFGEFHLLENEV-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  23
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-3-hexoxytetradecanoic acid 、 在 4-二甲氨基吡啶 、 二甲基氨基丙基乙基碳酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 C₈₂H₁₅₂N₂O₁₃Si
  参考文献：
  名称：

  The ‘Ethereal’ nature of TLR4 agonism and antagonism in the AGP class of lipid A mimetics

  摘要：

  To overcome the chemical and metabolic instability of the secondary fatty acyl residues in the AGP class of lipid A mimetics, the secondary ether lipid analogs of the potent TLR4 agonist CRX-527 (2) and TLR4 antagonist CRX-526 (3) were synthesized and evaluated along with their ester counterparts for agonist/antagonist activity in both in vitro and in vivo models. Like CRX-527, the secondary ether lipid 4 showed potent agonist activity in both murine and human models. Ether lipid 5, on the other hand, showed potent TLR4 antagonist activity similar to CRX-526 in human cell assays, but did not display any antagonist activity in murine models and, in fact, was weakly agonistic. Glycolipids 2, 4, and 5 were synthesized via a new highly convergent method utilizing a common advanced intermediate strategy. A new method for preparing (R)-3-alkyloxytetradecanoic acids, a key component of ether lipids 4 and 5, is also described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.060
• 作为产物：
  描述：

  2-(4-bromophenyl)-2-oxoethyl (R)-3-(hexyloxy)tetradecanoate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到(3R)-3-hexoxytetradecanoic acid
  参考文献：
  名称：

  The ‘Ethereal’ nature of TLR4 agonism and antagonism in the AGP class of lipid A mimetics

  摘要：

  To overcome the chemical and metabolic instability of the secondary fatty acyl residues in the AGP class of lipid A mimetics, the secondary ether lipid analogs of the potent TLR4 agonist CRX-527 (2) and TLR4 antagonist CRX-526 (3) were synthesized and evaluated along with their ester counterparts for agonist/antagonist activity in both in vitro and in vivo models. Like CRX-527, the secondary ether lipid 4 showed potent agonist activity in both murine and human models. Ether lipid 5, on the other hand, showed potent TLR4 antagonist activity similar to CRX-526 in human cell assays, but did not display any antagonist activity in murine models and, in fact, was weakly agonistic. Glycolipids 2, 4, and 5 were synthesized via a new highly convergent method utilizing a common advanced intermediate strategy. A new method for preparing (R)-3-alkyloxytetradecanoic acids, a key component of ether lipids 4 and 5, is also described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.060

文献信息

• Certain aminoalkyl glucosaminide phosphate compounds and their use
  申请人：Johnson A. David

  公开号：US20050227943A1

  公开（公告）日：2005-10-13

  Compounds that are adjuvants and immunoeffectors are described and claimed. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Compositions and methods for using the compounds as adjuvants and immunoeffectors are also disclosed.

  本文描述并声称了作为佐剂和免疫效应剂的化合物。 这些化合物能增强免疫动物体内抗体的产生，刺激细胞因子的产生并激活巨噬细胞。 还公开了将这些化合物用作佐剂和免疫效应剂的组合物和方法。
• CERTAIN AMINOALKYL GLUCOSAMINIDE PHOSPHATE COMPOUNDS AND THEIR USE
  申请人：CORIXA CORPORATION

  公开号：EP1589934A2

  公开（公告）日：2005-11-02
• EP1776375B1
  申请人：——

  公开号：EP1776375B1

  公开（公告）日：2015-04-01
• US7960522B2
  申请人：——

  公开号：US7960522B2

  公开（公告）日：2011-06-14
• [EN] CERTAIN AMINOALKYL GLUCOSAMINIDE PHOSPHATE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSES D'AMINOALKYLE GLUCOSAMINIDE PHOSPHATE ET LEUR UTILISATION
  申请人：CORIXA CORP

  公开号：WO2004062599A2

  公开（公告）日：2004-07-29

  Compounds that are adjuvants and immunoeffectors are described and claimed. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Compositions and methods for using the compounds as adjuvants and immunoeffectors are also disclosed.