tert-butyl-{[1-(ethoxymethyl)-1H-indol-2-yl]carbonyl}[3-(2-iodophenyl)propyl]carbamate | 1189788-01-9

• 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: tert-butyl-{[1-(ethoxymethyl)-1H-indol-2-yl]carbonyl}[3-(2-iodophenyl)propyl]carbamate
• 英文别名: tert-butyl N-[1-(ethoxymethyl)indole-2-carbonyl]-N-[3-(2-iodophenyl)propyl]carbamate
• CAS: 1189788-01-9
• 化学式: C₂₆H₃₁IN₂O₄
• 分子量: 562.448
• InChiKey: IIGCSMNVMCQVRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl-{[1-(ethoxymethyl)-1H-indol-2-yl]carbonyl}[3-(2-iodophenyl)propyl]carbamate 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 1.0h， 以47%的产率得到tert-butyl-10-(ethoxymethyl)-9-oxo-5,6,7,10-tetrahydroindolo[2,3-f][4]benzazonine-8-carboxylate
  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：

  二碳酸二叔丁酯 、 1-(ethoxymethyl)-N-[3-(2-iodophenyl)propyl]-1H-indole-2-carboxamide 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以99%的产率得到tert-butyl-{[1-(ethoxymethyl)-1H-indol-2-yl]carbonyl}[3-(2-iodophenyl)propyl]carbamate
  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