6,11-dihydro-11-[4-[4-(4,4,5,5,5-pentafluoropentylsulfonyl)butoxy]benzyl]-3,8-di-(tetrahydropyran-2-yloxy)-5H-benzo[a]carbazole | 307943-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6,11-dihydro-11-[4-[4-(4,4,5,5,5-pentafluoropentylsulfonyl)butoxy]benzyl]-3,8-di-(tetrahydropyran-2-yloxy)-5H-benzo[a]carbazole
• CAS: 307943-45-9
• 化学式: C₄₂H₄₈F₅NO₇S
• 分子量: 805.904
• InChiKey: KPUNUHFGIZTERT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.82
• 重原子数：
  56.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  85.22
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6,11-dihydro-11-[4-[4-(4,4,5,5,5-pentafluoropentylsulfonyl)butoxy]benzyl]-3,8-di-(tetrahydropyran-2-yloxy)-5H-benzo[a]carbazole 在 草酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.5h， 以64%的产率得到6,11-dihydro-3,8-dihydroxy-11-[4-[4-(4,4,5,5,5-pentafluoropentylsulfonyl)butoxy]benzyl]-5H-benzo[a]carbazole
  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 lithium aluminium tetrahydride 、 sodium methylate 、 三溴化磷 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 6,11-dihydro-11-[4-[4-(4,4,5,5,5-pentafluoropentylsulfonyl)butoxy]benzyl]-3,8-di-(tetrahydropyran-2-yloxy)-5H-benzo[a]carbazole
  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