{(4S,5S)3-hexadecanoyl-4-[4-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethoxy)-benzyl]-2,2-dimethyl-oxazolidin-5-ylmethyl}-phosphonic acid dimethyl ester | 1025112-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: {(4S,5S)3-hexadecanoyl-4-[4-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethoxy)-benzyl]-2,2-dimethyl-oxazolidin-5-ylmethyl}-phosphonic acid dimethyl ester
• CAS: 1025112-86-0
• 化学式: C₄₀H₆₅N₂O₇P
• 分子量: 716.939
• InChiKey: NYZGHNBBWAUEGF-PQQNNWGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.13
• 重原子数：
  50.0
• 可旋转键数：
  24.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  96.42
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  dimethyl (3S)-2-hydroxy-4-(4-((4-methoxy-3,5-dimethylpyridin-2-yl)methoxy)phenyl)-3-palmitamidobutylphosphonate 、 2-甲氧基丙烯 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到{(4S,5S)3-hexadecanoyl-4-[4-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethoxy)-benzyl]-2,2-dimethyl-oxazolidin-5-ylmethyl}-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