2-((1H,1H,2H,2H-perfluorodecyl)oxy)-2-oxoethyl-3-(pyridin-3-yl)propanoate | 1588777-15-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-((1H,1H,2H,2H-perfluorodecyl)oxy)-2-oxoethyl-3-(pyridin-3-yl)propanoate
• 英文别名: [2-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluorodecoxy)-2-oxoethyl] 3-pyridin-3-ylpropanoate；[2-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecoxy)-2-oxoethyl] 3-pyridin-3-ylpropanoate
• CAS: 1588777-15-4
• 化学式: C₂₀H₁₄F₁₇NO₄
• 分子量: 655.308
• InChiKey: SBCGKOPDOMEEPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  [Ru(p-cymene)Cl₂]₂ 、 2-((1H,1H,2H,2H-perfluorodecyl)oxy)-2-oxoethyl-3-(pyridin-3-yl)propanoate 以 二氯甲烷 为溶剂， 反应 96.0h， 以97%的产率得到[Ru(η6-p-cymene)Cl₂(2-((1H,1H,2H,2H-perfluorodecyl)oxy)-2-oxoethyl-3-(pyridin-3-yl)propanoate)]
  参考文献：
  名称：

  Discovery of a Highly Tumor-Selective Organometallic Ruthenium(II)–Arene Complex

  摘要：

  A ruthenium(II)-arene complex with a perfluoroalkyl-ligand was found to display remarkable selectivity toward cancer cells. IC50 values on several cancer cell lines are in the range of 25-45 mu M, and no cytotoxic effect was observed on nontumorigenic (HEK-293) cells at concentrations up to 500 mu M (the maximum concentration tested). Consequently, this complex was used as the basis for the development of a number of related derivatives, which were screened in cancerous and noncancerous cell lines. The lead compound was then evaluated in vivo for antiangiogenic activity in the CAM model and in a xenografted ovarian carcinoma tumor (A2780) grown on the CAM. A 90% reduction in the tumor growth was observed.

  DOI：

  10.1021/jm5002748
• 作为产物：
  描述：

  1H,1H,2H,2H-全氟-1-癸醇 、 2-吡啶乙酸盐酸盐 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以57%的产率得到2-((1H,1H,2H,2H-perfluorodecyl)oxy)-2-oxoethyl-3-(pyridin-3-yl)propanoate
  参考文献：
  名称：

  Discovery of a Highly Tumor-Selective Organometallic Ruthenium(II)–Arene Complex

  摘要：

  A ruthenium(II)-arene complex with a perfluoroalkyl-ligand was found to display remarkable selectivity toward cancer cells. IC50 values on several cancer cell lines are in the range of 25-45 mu M, and no cytotoxic effect was observed on nontumorigenic (HEK-293) cells at concentrations up to 500 mu M (the maximum concentration tested). Consequently, this complex was used as the basis for the development of a number of related derivatives, which were screened in cancerous and noncancerous cell lines. The lead compound was then evaluated in vivo for antiangiogenic activity in the CAM model and in a xenografted ovarian carcinoma tumor (A2780) grown on the CAM. A 90% reduction in the tumor growth was observed.

  DOI：

  10.1021/jm5002748

文献信息

• Discovery of a Highly Tumor-Selective Organometallic Ruthenium(II)–Arene Complex
  作者：Catherine M. Clavel、Emilia Păunescu、Patrycja Nowak-Sliwinska、Arjan W. Griffioen、Rosario Scopelliti、Paul J. Dyson

  DOI：10.1021/jm5002748

  日期：2014.4.24

  A ruthenium(II)-arene complex with a perfluoroalkyl-ligand was found to display remarkable selectivity toward cancer cells. IC50 values on several cancer cell lines are in the range of 25-45 mu M, and no cytotoxic effect was observed on nontumorigenic (HEK-293) cells at concentrations up to 500 mu M (the maximum concentration tested). Consequently, this complex was used as the basis for the development of a number of related derivatives, which were screened in cancerous and noncancerous cell lines. The lead compound was then evaluated in vivo for antiangiogenic activity in the CAM model and in a xenografted ovarian carcinoma tumor (A2780) grown on the CAM. A 90% reduction in the tumor growth was observed.