[1-(Benzenesulfonyl)-6-methoxyindol-3-yl]-(3,4,5-trimethoxyphenyl)methanone | 896462-36-5

• 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: [1-(Benzenesulfonyl)-6-methoxyindol-3-yl]-(3,4,5-trimethoxyphenyl)methanone
• CAS: 896462-36-5
• 化学式: C₂₅H₂₃NO₇S
• 分子量: 481.526
• InChiKey: VSYFUOBRYKWBRK-UHFFFAOYSA-N

物化性质

• 熔点：
  162-165 °C(Solv: dichloromethane (75-09-2); methanol (67-56-1))
• 沸点：
  690.0±65.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [1-(Benzenesulfonyl)-6-methoxyindol-3-yl]-(3,4,5-trimethoxyphenyl)methanone 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以94%的产率得到(6-methoxy-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of (3,4,5-trimethoxyphenyl)indol-3-ylmethane derivatives as potential antivascular agents

  摘要：

  Combretastatin A-4 (CSA-4), a stilbene derivative, is a potent vascular disrupting agent (VDA) with the structural requirement of a cis-configuration to maintain a molecular geometry and a correct orientation of both phenyl groups. A series of indolic analogues of CSA-4 was synthesized by means of an efficient strategy. Six compounds (20b, 25b-27b, 32b, and 35b) were identified as potent inhibitors of tubulin polymerization and also displayed cytotoxic activities on B16 melanoma cells at a nanomolar level. Both activities were well correlated with the ability to induce morphological changes of EA-hy 926 endothelial cells. In conclusion, the cis-stilbene skeleton of CSA-4 could conveniently be replaced by the 3-aroylindolic moiety, thus avoiding any isomerization leading to inactive trans compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.037
• 作为产物：
  描述：

  N-(3-甲氧基苯基)苯磺酰胺 在 三氯化铝 、 三氟化硼乙醚 、 碳酸氢钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 [1-(Benzenesulfonyl)-6-methoxyindol-3-yl]-(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of (3,4,5-trimethoxyphenyl)indol-3-ylmethane derivatives as potential antivascular agents

  摘要：

  Combretastatin A-4 (CSA-4), a stilbene derivative, is a potent vascular disrupting agent (VDA) with the structural requirement of a cis-configuration to maintain a molecular geometry and a correct orientation of both phenyl groups. A series of indolic analogues of CSA-4 was synthesized by means of an efficient strategy. Six compounds (20b, 25b-27b, 32b, and 35b) were identified as potent inhibitors of tubulin polymerization and also displayed cytotoxic activities on B16 melanoma cells at a nanomolar level. Both activities were well correlated with the ability to induce morphological changes of EA-hy 926 endothelial cells. In conclusion, the cis-stilbene skeleton of CSA-4 could conveniently be replaced by the 3-aroylindolic moiety, thus avoiding any isomerization leading to inactive trans compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.037

文献信息

• Synthesis and biological evaluation of (3,4,5-trimethoxyphenyl)indol-3-ylmethane derivatives as potential antivascular agents
  作者：Grégory Dupeyre、Guy G. Chabot、Sylviane Thoret、Xavier Cachet、Johanne Seguin、Daniel Guénard、François Tillequin、Daniel Scherman、Michel Koch、Sylvie Michel

  DOI：10.1016/j.bmc.2006.02.037

  日期：2006.7

  Combretastatin A-4 (CSA-4), a stilbene derivative, is a potent vascular disrupting agent (VDA) with the structural requirement of a cis-configuration to maintain a molecular geometry and a correct orientation of both phenyl groups. A series of indolic analogues of CSA-4 was synthesized by means of an efficient strategy. Six compounds (20b, 25b-27b, 32b, and 35b) were identified as potent inhibitors of tubulin polymerization and also displayed cytotoxic activities on B16 melanoma cells at a nanomolar level. Both activities were well correlated with the ability to induce morphological changes of EA-hy 926 endothelial cells. In conclusion, the cis-stilbene skeleton of CSA-4 could conveniently be replaced by the 3-aroylindolic moiety, thus avoiding any isomerization leading to inactive trans compounds. (c) 2006 Elsevier Ltd. All rights reserved.