tert-butyl N-methyl-N-[11-[(7S,8R,9S,13S,14S,17S)-13-methyl-3,17-bis[(2-methylpropan-2-yl)oxy]-6-oxo-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-7-yl]undecyl]carbamate | 402570-29-0

• 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: tert-butyl N-methyl-N-[11-[(7S,8R,9S,13S,14S,17S)-13-methyl-3,17-bis[(2-methylpropan-2-yl)oxy]-6-oxo-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-7-yl]undecyl]carbamate
• CAS: 402570-29-0
• 化学式: C₄₃H₇₁NO₅
• 分子量: 682.04
• InChiKey: WLYJLCYIDMZRJH-YEXSPBJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-methyl-N-[11-[(7S,8R,9S,13S,14S,17S)-13-methyl-3,17-bis[(2-methylpropan-2-yl)oxy]-6-oxo-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-7-yl]undecyl]carbamate 在 10percent palladium on carbon 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以81%的产率得到tert-butyl N-methyl-N-[11-[(7R,8R,9S,13S,14S,17S)-13-methyl-3,17-bis[(2-methylpropan-2-yl)oxy]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-yl]undecyl]carbamate
  参考文献：
  名称：

  Synthesis of Chimeric 7α-Substituted Estradiol Derivatives Linked to Cholesterol and Cholesterylamine

  摘要：

  We report the synthesis of 7alpha-substituted beta-estradiol derivatives bearing side chains terminated with cholesterol and 3beta-cholesterylamine. These chimeric compounds were designed to exhibit high affinity for estrogen receptors (ERs) and cellular plasma membranes to potentially enable regulated uptake of ERs by mammalian cells. Evaluation with recombinant yeast reporting compound-mediated ER dimerization revealed potencies similar to the antiestrogen ICI 182780. Compounds that efficiently deliver dominant negative ERs into cells may provide novel therapeutics against breast cancers.

  DOI：

  10.1021/ol0171261
• 作为产物：
  描述：

  3,17β-Bis-(tert.-butyloxy)-oestratrien-(1,3,5(10)) 在 2,2,6,6-tetramethyl-piperidine-N-oxyl sodium hypochlorite 、 potassium tert-butylate 、 碳酸氢钠 、 potassium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 8.75h， 生成 tert-butyl N-methyl-N-[11-[(7S,8R,9S,13S,14S,17S)-13-methyl-3,17-bis[(2-methylpropan-2-yl)oxy]-6-oxo-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-7-yl]undecyl]carbamate
  参考文献：
  名称：

  Synthesis of Chimeric 7α-Substituted Estradiol Derivatives Linked to Cholesterol and Cholesterylamine

  摘要：

  We report the synthesis of 7alpha-substituted beta-estradiol derivatives bearing side chains terminated with cholesterol and 3beta-cholesterylamine. These chimeric compounds were designed to exhibit high affinity for estrogen receptors (ERs) and cellular plasma membranes to potentially enable regulated uptake of ERs by mammalian cells. Evaluation with recombinant yeast reporting compound-mediated ER dimerization revealed potencies similar to the antiestrogen ICI 182780. Compounds that efficiently deliver dominant negative ERs into cells may provide novel therapeutics against breast cancers.

  DOI：

  10.1021/ol0171261