4-benzyloxy-5-methoxy-1-methylindole-3-carboxamide | 148674-73-1

• 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: 4-benzyloxy-5-methoxy-1-methylindole-3-carboxamide
• 英文别名: 5-Methoxy-1-methyl-4-phenylmethoxyindole-3-carboxamide
• CAS: 148674-73-1
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: VGOVQIINMRNVSE-UHFFFAOYSA-N

物化性质

• 沸点：
  553.3±45.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-5-methoxy-1-methylindole-3-carboxamide 在 劳森试剂 、 potassium nitrososulfonate 、 NaH₂PO₄-buffer 、 氨 作用下， 以 乙醇 、 丙酮 、 苯 为溶剂， 生成 BE-10988
  参考文献：
  名称：

  Synthesis of the topoisomerase II inhibitor BE 10988

  摘要：

  The naturally occurring indolequinone BE 10988 1, an inhibitor of topoisomerase II, has been synthesised in an overall yield of 28%.

  DOI：

  10.1016/s0040-4039(00)91982-8
• 作为产物：
  描述：

  4-苄氧基-5-甲氧基吲哚 在 偶氮二异丁腈 、 三正丁基氢锡 、 potassium hydride 作用下， 以 乙醚 、 苯 为溶剂， 反应 2.83h， 生成 4-benzyloxy-5-methoxy-1-methylindole-3-carboxamide
  参考文献：
  名称：

  Moody, Christopher J.; Swann, Elizabeth, Journal of the Chemical Society. Perkin transactions I, 1993, # 21, p. 2561 - 2566

  摘要：

  DOI：

文献信息

• Synthesis and Biological Activity of Thiazolylindolequinones, Analogs of the Natural Product BE 10988
  作者：Christopher J. Moody、Elizabeth Swann、Susan Houlbrook、Miriam A. Stephens、Ian J. Stratford

  DOI：10.1021/jm00006a024

  日期：1995.3

  A number of analogues of the naturally occurring thiazolylindolequinone BE 10988, a reported potent inhibitor of topoisomerase II, have been prepared and evaluated. The compounds were synthesized from 4-(benzyloxy)-S-methoxy-1-methylindole by appropriate substitution at the indole 3-position followed by standard thiazole ring-forming reactions. The toxicity of these potentially bioreductively activated indolequinones was measured in Chinese hamster V79 cells under aerobic and hypoxic conditions. In addition, toxicity was measured in a human breast cancer cell line that shows amplification of the topo II alpha gene and hypersensitivity to known topo II inhibitors such as mAMSA and mitoxantrone. Using a DNA decatenation assay, a comparison was also made of the inhibitory effects of BE 10988 and mitoxantrone on topo II activity.
• Moody, Christopher J.; Swann, Elizabeth, Journal of the Chemical Society. Perkin transactions I, 1993, # 21, p. 2561 - 2566
  作者：Moody, Christopher J.、Swann, Elizabeth

  DOI：——

  日期：——
• Synthesis of the topoisomerase II inhibitor BE 10988
  作者：Christopher J. Moody、Elizabeth Swann

  DOI：10.1016/s0040-4039(00)91982-8

  日期：1993.3

  The naturally occurring indolequinone BE 10988 1, an inhibitor of topoisomerase II, has been synthesised in an overall yield of 28%.