13-methyl-17-[3-(2-phenylethynyl-phenylethynyl)-phenylethynyl]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol | 399566-79-1

• 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: 13-methyl-17-[3-(2-phenylethynyl-phenylethynyl)-phenylethynyl]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• 英文别名: (8R,9S,13S,14S,17S)-13-methyl-17-[2-[3-[2-[2-(2-phenylethynyl)phenyl]ethynyl]phenyl]ethynyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 399566-79-1
• 化学式: C₄₂H₃₆O₂
• 分子量: 572.747
• InChiKey: ZCBVQPOWRIKWNF-LPAYBXTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  13-methyl-17-[3-(2-phenylethynyl-phenylethynyl)-phenylethynyl]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol 以 异丙醇 为溶剂， 反应 3.0h， 生成 (8R,9S,13S,14S,17S)-13-Methyl-17-[3-(3-phenyl-naphthalen-2-yl)-phenylethynyl]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
  参考文献：
  名称：

  Chemical synthesis of hormone receptor probes: high affinity photoactivated enediyne-estrogens

  摘要：

  A family of enediyne-estrogens has been prepared, and evaluated for affinity to hER. The optimal ligand has nM affinity, and undergoes photoBergman cycloaromatization. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01902-5
• 作为产物：
  描述：

  trimethyl((2-(phenylethynyl)phenyl)ethynyl)silane 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 13-methyl-17-[3-(2-phenylethynyl-phenylethynyl)-phenylethynyl]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
  参考文献：
  名称：

  Synthesis and Protein Degradation Capacity of Photoactivated Enediynes

  摘要：

  The viability of proteins as targets of thermally and photoactivated enediynes has been confirmed at the molecular level. Model studies using a labeled substrate confirmed the efficacy of atom transfer from diyl radicals produced from enediynes to form captodatively stabilized carbon centered aminoacyl radicals, which then undergo either fragmentation or dimerization. To exploit this finding, a family of enediynes was developed using an intramolecular coupling strategy. Derivatives were prepared and used to target specific proteins, showing good correlation between affinity and photoinduced protein degrading activity. The findings have potential applications in the design of artificial chemical proteases and add to our understanding of the mechanism of action of the clinically important enediyne antitumor antibiotics.

  DOI：

  10.1021/jo051403q