(8S,9R,11S,13S,14S,17S)-11-(4-(2-([2-propynyl]methylamino)ethoxy)phenyl)-7,8,9,11,12,13,14,15,16,17-decahydro-13-methyl-6H-cyclopenta[a]phenanthrene-3,17-diol | 1236153-25-5

• 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: (8S,9R,11S,13S,14S,17S)-11-(4-(2-([2-propynyl]methylamino)ethoxy)phenyl)-7,8,9,11,12,13,14,15,16,17-decahydro-13-methyl-6H-cyclopenta[a]phenanthrene-3,17-diol
• 英文别名: (8S,9R,11S,13S,14S,17S)-13-methyl-11-[4-[2-[methyl(prop-2-ynyl)amino]ethoxy]phenyl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 1236153-25-5
• 化学式: C₃₀H₃₇NO₃
• 分子量: 459.629
• InChiKey: PDAOTPDEVILGRQ-GDHIHDRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8S,9R,11S,13S,14S,17S)-11-(4-(2-([2-propynyl]methylamino)ethoxy)phenyl)-7,8,9,11,12,13,14,15,16,17-decahydro-13-methyl-6H-cyclopenta[a]phenanthrene-3,17-diol 、 在 copper(ll) sulfate pentahydrate sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 18.0h， 以46.9%的产率得到
  参考文献：
  名称：

  [EN] STEROIDAL ANTI-HORMONE HYBRIDS
  [FR] HYBRIDES ANTI-HORMONAUX STÉROÏDIENS

  摘要：

  披露了新颖的化合物和组合物，用于抑制雄激素和雌激素受体信号传导，抑制雄激素信号传导的方法，抑制雌激素信号传导的方法，抑制共调节蛋白与雄激素或雌激素受体之间相互作用的方法，以及治疗癌症的方法。

  公开号：

  WO2010085747A1
• 作为产物：
  描述：

  对(三甲基硅氧基)溴苯 在 sodium tetrahydroborate 、 copper(l) iodide 、 乙酰溴 、 水 、 碘 、 sodium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 50.5h， 生成 (8S,9R,11S,13S,14S,17S)-11-(4-(2-([2-propynyl]methylamino)ethoxy)phenyl)-7,8,9,11,12,13,14,15,16,17-decahydro-13-methyl-6H-cyclopenta[a]phenanthrene-3,17-diol
  参考文献：
  名称：

  Synthesis and preliminary evaluation steroidal antiestrogen–geldanamycin conjugates

  摘要：

  Three novel steroidal antiestrogen-geldanamycin conjugates were prepared using a convergent strategy. The antiestrogenic component utilized the 11 beta-(4-functionalized-oxyphenyl) estradiol scaffold, while the geldanamycin component was derived by replacement of the 17-methoxy group with an appropriately functionalized amine. Ligation was achieved in high yield using azide alkyne cyclization reactions. Evaluation of the products against two breast cancer cell lines indicated that the conjugates retained significant antiproliferative activity. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.03.116

文献信息

• [EN] STEROIDAL ANTI-HORMONE HYBRIDS<br/>[FR] HYBRIDES ANTI-HORMONAUX STÉROÏDIENS
  申请人：UNIV NORTHEASTERN

  公开号：WO2010085747A1

  公开（公告）日：2010-07-29

  Disclosed are novel compounds and compositions for inhibition of androgen and estrogen receptor signaling, methods for inhibiting androgen signaling, methods for inhibiting estrogen signaling, methods for inhibiting the interaction between a co-regulatory protein and an androgen or estrogen receptor, and methods for treating cancer.

  披露了新颖的化合物和组合物，用于抑制雄激素和雌激素受体信号传导，抑制雄激素信号传导的方法，抑制雌激素信号传导的方法，抑制共调节蛋白与雄激素或雌激素受体之间相互作用的方法，以及治疗癌症的方法。
• Synthesis and preliminary evaluation steroidal antiestrogen–geldanamycin conjugates
  作者：J. Adam Hendricks、Robert N. Hanson、Michael Amolins、John M. Mihelcic、Brian S. Blagg

  DOI：10.1016/j.bmcl.2013.03.116

  日期：2013.6

  Three novel steroidal antiestrogen-geldanamycin conjugates were prepared using a convergent strategy. The antiestrogenic component utilized the 11 beta-(4-functionalized-oxyphenyl) estradiol scaffold, while the geldanamycin component was derived by replacement of the 17-methoxy group with an appropriately functionalized amine. Ligation was achieved in high yield using azide alkyne cyclization reactions. Evaluation of the products against two breast cancer cell lines indicated that the conjugates retained significant antiproliferative activity. (C) 2013 Published by Elsevier Ltd.