[(3S)-1-fluoro-3-(hexadecanoylamino)-4-[4-[(4-methoxy-3,5-dimethylpyridin-2-yl)methoxy]phenyl]butyl]phosphonic acid | 1025112-55-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3S)-1-fluoro-3-(hexadecanoylamino)-4-[4-[(4-methoxy-3,5-dimethylpyridin-2-yl)methoxy]phenyl]butyl]phosphonic acid
• CAS: 1025112-55-3
• 化学式: C₃₅H₅₆FN₂O₆P
• 分子量: 650.812
• InChiKey: MSVXGQOQKOIRKG-JKNLKRECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  45
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  {1-fluoro-3-hexadecanoylamino-4-[4-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethoxy)-phenyl]-butyl}-phosphonic acid diethyl ester 在 三甲基溴硅烷 、 水 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以63%的产率得到[(3S)-1-fluoro-3-(hexadecanoylamino)-4-[4-[(4-methoxy-3,5-dimethylpyridin-2-yl)methoxy]phenyl]butyl]phosphonic acid
  参考文献：
  名称：

  α- and β-Substituted phosphonate analogs of LPA as autotaxin inhibitors

  摘要：

  Autotaxin (ATX) is an attractive pharmacological target due to its lysophospholipase D activity which leads to the production of lysophosphatidic acid (LPA). Blockage of ATX produced LPA by small molecules could be a potential anticancer chemotherapy. In our previous study, we have identified the two beta-hydroxy phosphonate analogs of LPA (compounds f17 and f18) as ATX inhibitors. With this work, we investigated alpha- and beta-substituted phosphonate analogs of LPA and evaluated them for ATX inhibitory activity. The stereochemistry of beta-hydroxy phosphonates was also studied. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2007.11.078

文献信息

• α- and β-Substituted phosphonate analogs of LPA as autotaxin inhibitors
  作者：Peng Cui、William F. McCalmont、Jose L. Tomsig、Kevin R. Lynch、Timothy L. Macdonald

  DOI：10.1016/j.bmc.2007.11.078

  日期：2008.3

  Autotaxin (ATX) is an attractive pharmacological target due to its lysophospholipase D activity which leads to the production of lysophosphatidic acid (LPA). Blockage of ATX produced LPA by small molecules could be a potential anticancer chemotherapy. In our previous study, we have identified the two beta-hydroxy phosphonate analogs of LPA (compounds f17 and f18) as ATX inhibitors. With this work, we investigated alpha- and beta-substituted phosphonate analogs of LPA and evaluated them for ATX inhibitory activity. The stereochemistry of beta-hydroxy phosphonates was also studied. Published by Elsevier Ltd.