[2-[(1R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]phenyl]boronic acid | 433969-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-[(1R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]phenyl]boronic acid
• CAS: 433969-28-9
• 化学式: C₁₃H₂₀BNO₄
• 分子量: 265.117
• InChiKey: UKDFPFINSUOQKA-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-[(1R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]phenyl]boronic acid 、 ethyl 3-iodo-1-phenylsulfonyl-2-indolecarboxylate 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60%的产率得到ethyl (R)-1-(benzenesulfonyl)-3-{2-[1-(tert-butyloxycarbonylamino)ethyl]phenyl}-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
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 生成 [2-[(1R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]phenyl]boronic acid
  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

文献信息

• New C5-Alkylated Indolobenzazepinones Acting as Inhibitors of Tubulin Polymerization: Cytotoxic and Antitumor Activities
  作者：Laurent Keller、Stéphane Beaumont、Jian-Miao Liu、Sylviane Thoret、Jérôme S. Bignon、Joanna Wdzieczak-Bakala、Philippe Dauban、Robert H. Dodd

  DOI：10.1021/jm701466p

  日期：2008.6.1

  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.