(S)-11-methoxy-5-methyl-5,8-dihydroindolo[2,3-d][2]benzazepin-7(6H)-one | 1034110-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: (S)-11-methoxy-5-methyl-5,8-dihydroindolo[2,3-d][2]benzazepin-7(6H)-one
• 英文别名: (8S)-16-methoxy-8-methyl-9,12-diazatetracyclo[9.7.0.02,7.013,18]octadeca-1(11),2,4,6,13(18),14,16-heptaen-10-one
• CAS: 1034110-80-9
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: FQDDIDRTIHMPOV-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 (S)-11-methoxy-5-methyl-5,8-dihydroindolo[2,3-d][2]benzazepin-7(6H)-one
  参考文献：
  名称：

  New C5-Alkylated Indolobenzazepinones Acting as Inhibitors of Tubulin Polymerization: Cytotoxic and Antitumor Activities

  摘要：

  A series of 5-alkylindolobenzazepin-7-ones was synthesized by Suzuki coupling between 3-iodoindole-2-carboxylates and the appropriate alpha-alkylbenzylamino o-boronic acids followed by cyclization to the lactam. Derivatives having a linear alkyl chain at C5 were found to be highly cytotoxic to KB cells with IC50 values in the 30-80 nM range. These compounds also inhibited the polymerization of tubulin with IC50's of 1-2 mu M. Compound 4f ((S)-5-ethyl) showed comparable antiproliferative activities (IC50's of 30-70 nM) in a variety of cancer cell lines, cell growth being arrested at the G2/M phase. Compound 4f induced apoptosis in a dose-dependent manner in three different cancer cell lines and was shown to affect cell morphology in a manner consistent with its inhibitory action on tubulin polymerization. Using the experimental model of glioma grafted on the chick chorio-allantoic membrane, local treatment with compound 4f markedly reduced tumor progression.

  DOI：

  10.1021/jm701466p