tert-butyl 8-(ethoxymethyl)-1-methoxy-7-oxo-5,8-dihydroindolo[2,3-d][2]benzazepine-6-carboxylate | 1189788-29-1

• 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 8-(ethoxymethyl)-1-methoxy-7-oxo-5,8-dihydroindolo[2,3-d][2]benzazepine-6-carboxylate
• 英文别名: Tert-butyl 12-(ethoxymethyl)-3-methoxy-10-oxo-9,12-diazatetracyclo[9.7.0.02,7.013,18]octadeca-1(11),2(7),3,5,13,15,17-heptaene-9-carboxylate
• CAS: 1189788-29-1
• 化学式: C₂₅H₂₈N₂O₅
• 分子量: 436.508
• InChiKey: OEMNKAJVZWBGIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 8-(ethoxymethyl)-1-methoxy-7-oxo-5,8-dihydroindolo[2,3-d][2]benzazepine-6-carboxylate 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以20%的产率得到1-methoxy-5,8-dihydroindolo[2,3-d][2]benzazepin-7(6H)-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：

  tert-butyl {[1-(ethoxymethyl)-1H-indol-2-yl]carbonyl}(2-iodo-3-methoxybenzyl)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73%的产率得到tert-butyl 8-(ethoxymethyl)-1-methoxy-7-oxo-5,8-dihydroindolo[2,3-d][2]benzazepine-6-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