Dodecanoic acid (2-ethoxy-3-hydroxy-propyl)-amide | 688802-57-5

• 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: Dodecanoic acid (2-ethoxy-3-hydroxy-propyl)-amide
• CAS: 688802-57-5
• 化学式: C₁₇H₃₅NO₃
• 分子量: 301.47
• InChiKey: KPTIKIFJCSPNRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  21.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Dodecanoic acid (2-ethoxy-3-hydroxy-propyl)-amide 生成 3-dodecylamido-2-ethoxypropylphosphocholine
  参考文献：
  名称：

  Methods and compositions for the treatment of respiratory syncytial virus

  摘要：

  该发明包括用于抑制RSV复制和治疗感染RSV的宿主的化合物。该发明还包括通过向宿主施用该发明的化合物的抗RSV有效量来治疗感染RSV的宿主的方法。

  公开号：

  US20050187191A1
• 作为产物：
  描述：

  3-lauroylamino-1,2-propanediol 在 对甲苯磺酸 作用下， 生成 Dodecanoic acid (2-ethoxy-3-hydroxy-propyl)-amide
  参考文献：
  名称：

  Methods and compositions for the treatment of respiratory syncytial virus

  摘要：

  该发明包括用于抑制RSV复制和治疗感染RSV的宿主的化合物。该发明还包括通过向宿主施用该发明的化合物的抗RSV有效量来治疗感染RSV的宿主的方法。

  公开号：

  US20050187191A1

文献信息

• Structure−Activity Relationship for Enhancement of Paracellular Permeability across Caco-2 Cell Monolayers by 3-Alkylamido-2-alkoxypropylphosphocholines
  作者：Hui Ouyang、Susan L. Morris-Natschke、Khalid S. Ishaq、Peter Ward、Dongzhou Liu、Sarah Leonard、Dhiren R. Thakker

  DOI：10.1021/jm020001x

  日期：2002.6.1

  Paracellular permeability enhancers have been used to improve the oral bioavailability of hydrophilic drugs; however, the mechanism of action of many enhancers is poorly understood. In this study, highly potent enhancers of paracellular permeability were identified in the 3-alkylamido-2-alkoxypropylphosphocholine series, and a structure-activity relationship was developed for enhancement of paracellular permeability across Caco-2 cell monolayers. Compounds with short (<5 carbons) hydrocarbon chains at both C-2 and C-3 were generally inactive. The potency exhibited a parabolic relationship with respect to the chain length at either C-2 or C-3. Linear molecules (i.e., compounds with a short hydrocarbon chain at C-2 or C-3 and a long hydrocarbon chain on C-3 or C-2, respectively) were more potent than the corresponding branched molecules with the same carbon load. The efficacy of 3-alkylamido2-alkoxypropylphosphocholines as enhancers of paracellular permeability was not dependent on their existence in micellar form or their ability to alter the fluidity of cell membrane. Previously, a correlation-between the potency of alkylphosphocholines as enhancers of paracellular permeability and the inhibitors of phospholipase C (PLC) was established in Madine Darby canine kidney (MDCK) cell monolayers. The potencies of selected 3-alkylamido-2-alkoxypropylphosphocholines as inhibitors of PLC and enhancers of paracellular permeability fit well into this correlation. Therefore, phosphocholines are likely to increase paracellular permeability by modulating the signal transduction pathway initiated by a PLC-catalyzed reaction rather than by physically altering the cell membrane.