(S)-dimethyl 4-(4-((3,5-dimethylpyridin-2-yl)methoxy)phenyl)-2-oxo-3-palmitamidobutylphosphonate | 1260021-98-4

• 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: (S)-dimethyl 4-(4-((3,5-dimethylpyridin-2-yl)methoxy)phenyl)-2-oxo-3-palmitamidobutylphosphonate
• CAS: 1260021-98-4
• 化学式: C₃₆H₅₇N₂O₆P
• 分子量: 644.832
• InChiKey: OHKSAKPVYMRARH-XIFFEERXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.84
• 重原子数：
  45.0
• 可旋转键数：
  25.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  103.82
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-dimethyl 4-(4-((3,5-dimethylpyridin-2-yl)methoxy)phenyl)-2-oxo-3-palmitamidobutylphosphonate 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 dimethyl (3S)-4-(4-((3,5-dimethylpyridin-2-yl)methoxy)phenyl)-2-hydroxy-3-palmitamidobutylphosphonate 、 dimethyl (3S)-4-(4-((3,5-dimethylpyridin-2-yl)methoxy)phenyl)-2-hydroxy-3-palmitamidobutylphosphonate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of tyrosine-based inhibitors of autotaxin (ATX)

  摘要：

  Autotaxin (ATX) is a secreted soluble enzyme that generates lysophosphatidic acid (LPA) through its lysophospholipase D activity. Because of LPA's role in neoplastic diseases, ATX is an attractive therapeutic target due to its involvement in LPA biosynthesis. Here we describe the SAR of ATX inhibitor, VPC8a202, and apply this SAR knowledge towards developing a high potency inhibitor. We found that electron density in the pyridine region greatly influences activity of our inhibitors at ATX. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.030
• 作为产物：
  描述：

  (S)-methyl 3-(4-((3,5-dimethylpyridin-2-yl)methoxy)phenyl)-2-palmitamidopropanoate 、 甲基膦酸二甲酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.58h， 以61%的产率得到(S)-dimethyl 4-(4-((3,5-dimethylpyridin-2-yl)methoxy)phenyl)-2-oxo-3-palmitamidobutylphosphonate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of tyrosine-based inhibitors of autotaxin (ATX)

  摘要：

  Autotaxin (ATX) is a secreted soluble enzyme that generates lysophosphatidic acid (LPA) through its lysophospholipase D activity. Because of LPA's role in neoplastic diseases, ATX is an attractive therapeutic target due to its involvement in LPA biosynthesis. Here we describe the SAR of ATX inhibitor, VPC8a202, and apply this SAR knowledge towards developing a high potency inhibitor. We found that electron density in the pyridine region greatly influences activity of our inhibitors at ATX. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.030