[(1S,3S)-4-(4-benzyloxy-phenyl)-3-hexadecanoylamino-1-hydroxy-butyl]-phosphonic acid dimethyl ester | 1025112-64-4

• 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: [(1S,3S)-4-(4-benzyloxy-phenyl)-3-hexadecanoylamino-1-hydroxy-butyl]-phosphonic acid dimethyl ester
• CAS: 1025112-64-4
• 化学式: C₃₅H₅₆NO₆P
• 分子量: 617.807
• InChiKey: OTYBMECVBZFNAI-SHUZPENHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.97
• 重原子数：
  43.0
• 可旋转键数：
  25.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  94.09
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [(1S,3S)-4-(4-benzyloxy-phenyl)-3-hexadecanoylamino-1-hydroxy-butyl]-phosphonic acid dimethyl ester 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以58%的产率得到[(1S,3S)-3-hexadecanoylamino-1-hydroxy-4-(4-hydroxyphenyl)-butyl]-phosphonic acid dimethyl ester
  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
• 作为产物：
  描述：

  、 棕榈酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(1S,3S)-4-(4-benzyloxy-phenyl)-3-hexadecanoylamino-1-hydroxy-butyl]-phosphonic acid dimethyl ester 、 [(1R,3S)-4-(4-benzyloxy-phenyl)-3-hexadecanoylamino-1-hydroxy-butyl]-phosphonic acid dimethyl ester
  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