1-bromo-10-(4,4,5,5,5-pentafluoropentylthio)decane | 307943-46-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-bromo-10-(4,4,5,5,5-pentafluoropentylthio)decane
• CAS: 307943-46-0
• 化学式: C₁₅H₂₆BrF₅S
• 分子量: 413.333
• InChiKey: KDMKSTLPHRDNQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.21
• 重原子数：
  22.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-bromo-10-(4,4,5,5,5-pentafluoropentylthio)decane 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 5-methoxy-2-(4-methoxyphenyl)-3-methyl-1-[10-(4,4,5,5,5-pentafluoropentylsulfonyl)decyl]indole
  参考文献：
  名称：

  Antiestrogenic Activities of 3,8-Dihydroxy-6,11-dihydrobenzo[a]carbazoles with Sulfur-Containing Side Chains

  摘要：

  The objective of this study was to explore whether the conversion of the 2-phenylindole system into the tetracyclic benzo[a]carbazole changes the endocrine profile when the side chain structure was kept constant. Five different sulfur-containing side chains were linked to the nitrogen of the tetracycle. The biological evaluation revealed that the character of the indole derivatives remained unchanged after the conversion to the respective benzocarbzoles but the potency decreased by one order of magnitude. In vitro, all derivatives acted as pure antiestrogens without any agonist activity. They strongly inhibited the growth of estrogen-sensitive MCF-7 breast cancer cells with IC50-values in the nanomolar range. In the mouse uterine weight test, the derivatives with an aliphatic side chain were devoid of estrogenic activity and antagonized the effect of estradiol. The presence of an aromatic ring in the side chain gave rise to significant agonist activity in vivo independently of the carrier structure. All data revealed the equivalence of both carrier structures in respect to the endocrine profile but showed a decrease in potency upon the conversion of the 2-phenylindole system into the benzocarbazole structure.

  DOI：

  10.1002/1521-4184(20009)333:9<305::aid-ardp305>3.0.co;2-q
• 作为产物：
  描述：

  1-(acetylsulfanyl)-4,4,5,5,5-pentafluoropentane 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-bromo-10-(4,4,5,5,5-pentafluoropentylthio)decane
  参考文献：
  名称：

  Antiestrogenic Activities of 3,8-Dihydroxy-6,11-dihydrobenzo[a]carbazoles with Sulfur-Containing Side Chains

  摘要：

  The objective of this study was to explore whether the conversion of the 2-phenylindole system into the tetracyclic benzo[a]carbazole changes the endocrine profile when the side chain structure was kept constant. Five different sulfur-containing side chains were linked to the nitrogen of the tetracycle. The biological evaluation revealed that the character of the indole derivatives remained unchanged after the conversion to the respective benzocarbzoles but the potency decreased by one order of magnitude. In vitro, all derivatives acted as pure antiestrogens without any agonist activity. They strongly inhibited the growth of estrogen-sensitive MCF-7 breast cancer cells with IC50-values in the nanomolar range. In the mouse uterine weight test, the derivatives with an aliphatic side chain were devoid of estrogenic activity and antagonized the effect of estradiol. The presence of an aromatic ring in the side chain gave rise to significant agonist activity in vivo independently of the carrier structure. All data revealed the equivalence of both carrier structures in respect to the endocrine profile but showed a decrease in potency upon the conversion of the 2-phenylindole system into the benzocarbazole structure.

  DOI：

  10.1002/1521-4184(20009)333:9<305::aid-ardp305>3.0.co;2-q