3,17β-bis(2-tetrahydropyranyloxy)-7α-(5-hexen-1-yl)-estra-1,3,5(10)triene | 408512-82-3

• 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: 3,17β-bis(2-tetrahydropyranyloxy)-7α-(5-hexen-1-yl)-estra-1,3,5(10)triene
• 英文别名: 2-[[(7R,8R,9S,13S,14S,17S)-7-hex-5-enyl-13-methyl-3-(oxan-2-yloxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]oxy]oxane
• CAS: 408512-82-3
• 化学式: C₃₄H₅₀O₄
• 分子量: 522.769
• InChiKey: ONWRTRHBVORLPC-WRCDNKAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,17β-bis(2-tetrahydropyranyloxy)-7α-(5-hexen-1-yl)-estra-1,3,5(10)triene 在 硼烷 、 氢氧化钾 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以66%的产率得到3,17β-bis-(2-tetrahydropyranyloxy)-7α-(6-hydroxyhexan-1-yl)-estra-1,3,5(10)-triene
  参考文献：
  名称：

  A Rationally Designed Genotoxin that Selectively Destroys Estrogen Receptor-Positive Breast Cancer Cells

  摘要：

  We describe a novel strategy to increase the selective toxicity of genotoxic compounds. The strategy involves the synthesis of bifunctional molecules capable of forming DNA adducts that have high affinity for specific proteins in target cells. It is proposed that the association of such proteins with damaged sites in DNA can compromise protein function and/or DNA repair resulting in increased toxicity. We describe the synthesis of a bifunctional compound consisting of an aniline mustard linked to the 7alpha position of estradiol. This novel compound can form covalent DNA adducts that have high affinity for the estrogen receptor. Breast cancer cells that express high levels of the estrogen receptor showed increased sensitivity to the cytotoxic effects of the new compound.

  DOI：

  10.1021/ja017344p
• 作为产物：
  描述：

  雌二醇 在 三乙基硅烷 、 三乙基硼 、 三氟化硼乙醚 、 potassium tert-butylate 、 4-甲基苯磺酸吡啶 、 乙酰氯 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 26.83h， 生成 3,17β-bis(2-tetrahydropyranyloxy)-7α-(5-hexen-1-yl)-estra-1,3,5(10)triene
  参考文献：
  名称：

  A Rationally Designed Genotoxin that Selectively Destroys Estrogen Receptor-Positive Breast Cancer Cells

  摘要：

  We describe a novel strategy to increase the selective toxicity of genotoxic compounds. The strategy involves the synthesis of bifunctional molecules capable of forming DNA adducts that have high affinity for specific proteins in target cells. It is proposed that the association of such proteins with damaged sites in DNA can compromise protein function and/or DNA repair resulting in increased toxicity. We describe the synthesis of a bifunctional compound consisting of an aniline mustard linked to the 7alpha position of estradiol. This novel compound can form covalent DNA adducts that have high affinity for the estrogen receptor. Breast cancer cells that express high levels of the estrogen receptor showed increased sensitivity to the cytotoxic effects of the new compound.

  DOI：

  10.1021/ja017344p