7α-benzyloxymethyl-9-methyl-6β-(2'-methylindol-3'-yl)-5-tosyl-5,6α,6aβ,7β,8,10aβ-hexahydroindeno<2,1-b>indole | 142502-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 7α-benzyloxymethyl-9-methyl-6β-(2'-methylindol-3'-yl)-5-tosyl-5,6α,6aβ,7β,8,10aβ-hexahydroindeno<2,1-b>indole
• CAS: 142502-17-8
• 化学式: C₄₀H₃₈N₂O₃S
• 分子量: 626.819
• InChiKey: FEEMYGUAYCZTBV-XPCUQZLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.0
• 重原子数：
  46.0
• 可旋转键数：
  7.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.09
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7α-benzyloxymethyl-9-methyl-6β-(2'-methylindol-3'-yl)-5-tosyl-5,6α,6aβ,7β,8,10aβ-hexahydroindeno<2,1-b>indole 在 disodium hydrogenphosphate 、 sodium amalgam 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 以80%的产率得到7α-benzyloxymethyl-9-methyl-6β-(2'-methylindol-3'-yl)-5,6α,6aβ,7β,8,10aβ-hexahydroindeno<2,1-b>indole
  参考文献：
  名称：

  Structure-function relationship of Yuehchukene II. The effect of C-6 indole rotation on anti-implantation activity

  摘要：

  In a first attempts to define the structural requirements for the expression of anti-implantation activity in Yuehchukene (YCK), it was found that the relative position or planarity of the aromatic centres may be crucial. New synthetic routes leading to analogues with modification of C-7 substituents were established. Results indicated that a bulky group at C-7 that served to restrict the rotation of the C-6 indole was indispensable. Further steric hindrance by 2'-methyl would increase potency in all weak analogues. It was concluded that YCK required an optimal conformation that was defined by a narrowly-fixed angle between the, planes of the C-6 indole and the tetracyclic unit.

  DOI：

  10.1016/0223-5234(92)90100-f
• 作为产物：
  描述：

  7α-benzyloxymethyl-6α-hydroxy-9-methyl-5-tosyl-5,6β,6aβ,7β,8,10aβ-hexahydroindeno<2,1-b>indole 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 氯仿 、 苯 为溶剂， 反应 1.5h， 生成 7α-benzyloxymethyl-9-methyl-6β-(2'-methylindol-3'-yl)-5-tosyl-5,6α,6aβ,7β,8,10aβ-hexahydroindeno<2,1-b>indole
  参考文献：
  名称：

  Structure-function relationship of Yuehchukene II. The effect of C-6 indole rotation on anti-implantation activity

  摘要：

  In a first attempts to define the structural requirements for the expression of anti-implantation activity in Yuehchukene (YCK), it was found that the relative position or planarity of the aromatic centres may be crucial. New synthetic routes leading to analogues with modification of C-7 substituents were established. Results indicated that a bulky group at C-7 that served to restrict the rotation of the C-6 indole was indispensable. Further steric hindrance by 2'-methyl would increase potency in all weak analogues. It was concluded that YCK required an optimal conformation that was defined by a narrowly-fixed angle between the, planes of the C-6 indole and the tetracyclic unit.

  DOI：

  10.1016/0223-5234(92)90100-f