(R,S)-ethyl 1-(benzenesulfonyl)-3-{2-[1-(tert-butyloxycarbonylamino)propyl]phenyl}-5-fluoro-1H-indole-2-carboxylate | 1034110-61-6

• 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: (R,S)-ethyl 1-(benzenesulfonyl)-3-{2-[1-(tert-butyloxycarbonylamino)propyl]phenyl}-5-fluoro-1H-indole-2-carboxylate
• CAS: 1034110-61-6
• 化学式: C₃₁H₃₃FN₂O₆S
• 分子量: 580.677
• InChiKey: HNQYJIFCBFQKCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  103.7
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (R,S)-ethyl 1-(benzenesulfonyl)-3-{2-[1-(tert-butyloxycarbonylamino)propyl]phenyl}-5-fluoro-1H-indole-2-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  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
• 作为产物：
  描述：

  ethyl 1-(benzenesulfonyl)-5-fluoro-1H-3-iodoindole-2-carboxylate 、 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 20.0h， 以51%的产率得到(R,S)-ethyl 1-(benzenesulfonyl)-3-{2-[1-(tert-butyloxycarbonylamino)propyl]phenyl}-5-fluoro-1H-indole-2-carboxylate
  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