9-(ethoxymethyl)-7-methyl-5,6,7,9-tetrahydro-8H-indolo[2,3-e][3]benzazocin-8-one | 1189788-06-4

• 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: 9-(ethoxymethyl)-7-methyl-5,6,7,9-tetrahydro-8H-indolo[2,3-e][3]benzazocin-8-one
• 英文别名: 13-(Ethoxymethyl)-10-methyl-10,13-diazatetracyclo[10.7.0.02,7.014,19]nonadeca-1(12),2,4,6,14,16,18-heptaen-11-one
• CAS: 1189788-06-4
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: UUCUEPAOIACFHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-(ethoxymethyl)-7-methyl-5,6,7,9-tetrahydro-8H-indolo[2,3-e][3]benzazocin-8-one 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以67%的产率得到7-methyl-5,6,7,9-tetrahydroindolo[2,3-e][3]benzazocin-8-one
  参考文献：
  名称：

  Indolobenzazepin-7-ones and 6-, 8-, and 9-Membered Ring Derivatives as Tubulin Polymerization Inhibitors: Synthesis and Structure−Activity Relationship Studies

  摘要：

  Several small weight indole derivatives (D-64131, D-24851, BPR0L075, BLF 61-3, and ATI derivatives) are potent tubulin polymerization inhibitors and show nanomolar antiproliferative activity. Among them, indolobenzazepin-7-ones were recently disclosed as potent antimitotic agents. In an effort to improve this structure, we prepared new derivatives in order to evaluate their antiproliferative activity. 5,6,7,9-Tetrahydro-8H-indolo[2,3-e][3]benzazocin-g-one (1m) was found to be the most potent derivative inhibiting the cell growth of several cancer cell lines in the lower nanomolar range.

  DOI：

  10.1021/jm900476c
• 作为产物：
  描述：

  1-(ethoxymethyl)-N-[2-(2-iodophenyl)ethyl]-N-methyl-1H-indole-2-carboxamide 在 palladium diacetate 、 三苯基膦 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以87%的产率得到9-(ethoxymethyl)-7-methyl-5,6,7,9-tetrahydro-8H-indolo[2,3-e][3]benzazocin-8-one
  参考文献：
  名称：

  Indolobenzazepin-7-ones and 6-, 8-, and 9-Membered Ring Derivatives as Tubulin Polymerization Inhibitors: Synthesis and Structure−Activity Relationship Studies

  摘要：

  Several small weight indole derivatives (D-64131, D-24851, BPR0L075, BLF 61-3, and ATI derivatives) are potent tubulin polymerization inhibitors and show nanomolar antiproliferative activity. Among them, indolobenzazepin-7-ones were recently disclosed as potent antimitotic agents. In an effort to improve this structure, we prepared new derivatives in order to evaluate their antiproliferative activity. 5,6,7,9-Tetrahydro-8H-indolo[2,3-e][3]benzazocin-g-one (1m) was found to be the most potent derivative inhibiting the cell growth of several cancer cell lines in the lower nanomolar range.

  DOI：

  10.1021/jm900476c

文献信息

• Indolobenzazepin-7-ones and 6-, 8-, and 9-Membered Ring Derivatives as Tubulin Polymerization Inhibitors: Synthesis and Structure−Activity Relationship Studies
  作者：Aurélien Putey、Florence Popowycz、Quoc-Tuan Do、Philippe Bernard、Sandeep K. Talapatra、Frank Kozielski、Carlos M. Galmarini、Benoît Joseph

  DOI：10.1021/jm900476c

  日期：2009.10.8

  Several small weight indole derivatives (D-64131, D-24851, BPR0L075, BLF 61-3, and ATI derivatives) are potent tubulin polymerization inhibitors and show nanomolar antiproliferative activity. Among them, indolobenzazepin-7-ones were recently disclosed as potent antimitotic agents. In an effort to improve this structure, we prepared new derivatives in order to evaluate their antiproliferative activity. 5,6,7,9-Tetrahydro-8H-indolo[2,3-e][3]benzazocin-g-one (1m) was found to be the most potent derivative inhibiting the cell growth of several cancer cell lines in the lower nanomolar range.