(8R,9S,10R,13S,14S,17S)-13-ethyl-17-hydroxy-17-[2-(2-phenylpyridin-4-yl)ethynyl]-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one | 1328906-43-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (8R,9S,10R,13S,14S,17S)-13-ethyl-17-hydroxy-17-[2-(2-phenylpyridin-4-yl)ethynyl]-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 1328906-43-9
• 化学式: C₃₂H₃₅NO₂
• 分子量: 465.635
• InChiKey: JHOSPKNFMGYVGM-SWAQWBRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  左炔诺孕酮 、 4-溴-2-苯基吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 作用下， 反应 72.0h， 以87%的产率得到(8R,9S,10R,13S,14S,17S)-13-ethyl-17-hydroxy-17-[2-(2-phenylpyridin-4-yl)ethynyl]-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  A Potent Ruthenium(II) Antitumor Complex Bearing a Lipophilic Levonorgestrel Group

  摘要：

  The novel steroidal conjugate 17-alpha-[2-phenylpyridyl-4-ethynyl]-19-nortestosterone (LEV-ppy) (1) and the steroid-C,N-chelate ruthenium(II) conjugate [Ru(eta(6)-p-cymene)(LEV-ppy)Cl] (2) have been prepared. At 48 h incubation time, complex 2 is more active than cisplatin (about 8-fold) in T47D (breast cancer) and also shows an improved efficiency when compared to its nonsteroidal analogue [Ru(eta(6)-p-cymene)(ppy)Cl] (ppy = phenylpyridine) (3) in the same cell line. The act of conjugating a levonorgestrel group to a ruthenium(U) complex resulted in synergistic effects between the metallic center and the steroidal ligand, creating highly potent ruthenium(11) complexes from the inactive components. The interaction of 2 with DNA was followed by electrophoretic mobility. Theoretical density functional theory calculations on complex 2 show the metal center far away from the lipophilic steroidal moiety and a labile Ru-Cl bond that allows easy replacement of Cl by N-nucleophiles such as 9-EtG, thus forming a stronger Ru-N bond. We also found a minimum energy location for the chloride counteranion (4(+) center dot Cl-) inside the pseudocavity formed by the alpha side of the steroid moiety, the phenylpyridine chelating subsystem, and the guanine ligand, i.e., a host-guest species with a rich variety of nonbonding interactions that include nonclassical C-H center dot center dot center dot anion bonds, as supported by electrospray ionization mass spectra.

  DOI：

  10.1021/ic201388n