5-methoxy-2-naphthalen-2-yl-3-(3,4,5-trimethoxyphenyl)-1H-indole | 247172-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-methoxy-2-naphthalen-2-yl-3-(3,4,5-trimethoxyphenyl)-1H-indole
• CAS: 247172-13-0
• 化学式: C₂₈H₂₅NO₄
• 分子量: 439.511
• InChiKey: WGPSOEQCSVSMGP-UHFFFAOYSA-N

物化性质

• 熔点：
  142 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  599.1±50.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-naphthalen-2-yl-3-(3,4,5-trimethoxyphenyl)-1H-indole 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以75%的产率得到
  参考文献：
  名称：

  New naphthylcombretastatins. Modifications on the ethylene bridge

  摘要：

  Compounds with three aromatic systems, carrying a 2-naphthalene and a 3,4,5-trimethoxyphenyl moieties bonded to five-membered, six-membered or fused heterocycles display potent cytotoxic effect and inhibition of tubulin polymerization, in agreement with their structural similarity to combretastatins and their heterocyclic analogues. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.012
• 作为产物：
  描述：

  (4-甲氧基苯基)肼 、 1-(naphthalen-2-yl)-2-(3,4,5-trimethoxyphenyl)ethan-1-one 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以25%的产率得到5-methoxy-2-naphthalen-2-yl-3-(3,4,5-trimethoxyphenyl)-1H-indole
  参考文献：
  名称：

  New naphthylcombretastatins. Modifications on the ethylene bridge

  摘要：

  Compounds with three aromatic systems, carrying a 2-naphthalene and a 3,4,5-trimethoxyphenyl moieties bonded to five-membered, six-membered or fused heterocycles display potent cytotoxic effect and inhibition of tubulin polymerization, in agreement with their structural similarity to combretastatins and their heterocyclic analogues. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.012

文献信息

• Synthesis and pharmacological activity of diarylindole derivatives. Cytotoxic agents based on combretastatins
  作者：Manuel Medarde、Angel C. Ramos、Esther Caballero、Rafael Peláez-Lamaniéde Clairac、Jose Luis López、Dolores Ga Grávalos、Arturo San Feliciano

  DOI：10.1016/s0960-894x(99)00370-4

  日期：1999.8

  Taking into account the structure of Combretastatins, we have synthesized and assayed for cytotoxic activity of new indole derivatives. Two aryl groups are maintained in the cis orientation required for activity by means of an indole moiety built up on less active ketoderivatives used as starting materials. (C) 1999 Elsevier Science Ltd. All rights reserved.