3-[4-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethoxy)-phenyl]-2-octadecanoylamino-propionic acid methyl ester | 935547-95-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-[4-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethoxy)-phenyl]-2-octadecanoylamino-propionic acid methyl ester
• CAS: 935547-95-8
• 化学式: C₃₇H₅₈N₂O₅
• 分子量: 610.878
• InChiKey: YWDUUWDGZHTLHD-XIFFEERXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.75
• 重原子数：
  44.0
• 可旋转键数：
  24.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  86.75
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-[4-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethoxy)-phenyl]-2-octadecanoylamino-propionic acid methyl ester 在 sodium tetrahydroborate 、 正丁基锂 、 三甲基溴硅烷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 [(3S)-2-hydroxy-3-(icosanoylamino)-4-[4-[(4-methoxy-3,5-dimethylpyridin-2-yl)methoxy]phenyl]butyl]phosphonic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of phosphonate derivatives as autotaxin (ATX) inhibitors

  摘要：

  Autotaxin (ATX) is an autocrine motility factor that promotes cancer cell invasion, cell migration, and angiogenesis. ATX, originally discovered as a nucleotide phosphodiesterase, is known now to be responsible for the lysophospholipid-preferring phospholipase D activity in plasma. As such, it catalyzes the production of lysophosphatidic acid (LPA) from lysophophatidylcholine (LPC). ATX is thus an attractive drug target; small molecular inhibitors might be efficacious in slowing the spread of cancers. With this study we have generated a series of P-keto and P-hydroxy phosphonate derivatives of LPA, some of which are potent ATX inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.114
• 作为产物：
  描述：

  十八烷酰氯 在 18-冠醚-6 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.0h， 生成 3-[4-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethoxy)-phenyl]-2-octadecanoylamino-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of phosphonate derivatives as autotaxin (ATX) inhibitors

  摘要：

  Autotaxin (ATX) is an autocrine motility factor that promotes cancer cell invasion, cell migration, and angiogenesis. ATX, originally discovered as a nucleotide phosphodiesterase, is known now to be responsible for the lysophospholipid-preferring phospholipase D activity in plasma. As such, it catalyzes the production of lysophosphatidic acid (LPA) from lysophophatidylcholine (LPC). ATX is thus an attractive drug target; small molecular inhibitors might be efficacious in slowing the spread of cancers. With this study we have generated a series of P-keto and P-hydroxy phosphonate derivatives of LPA, some of which are potent ATX inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.114