[1-(benzenesulfonyl)indol-3-yl]-(3,4,5-trimethoxyphenyl)methanone | 896462-33-2

• 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)indol-3-yl]-(3,4,5-trimethoxyphenyl)methanone
• CAS: 896462-33-2
• 化学式: C₂₄H₂₁NO₆S
• 分子量: 451.5
• InChiKey: ZYIDRIUVWOVBGQ-UHFFFAOYSA-N

物化性质

• 熔点：
  142-143 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  665.8±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)：
  4.14
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.83
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [1-(benzenesulfonyl)indol-3-yl]-(3,4,5-trimethoxyphenyl)methanone 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.08h， 以95%的产率得到(1-Benzenesulfonyl-1H-indol-3-yl)-(3,4,5-trimethoxy-phenyl)-methanol
  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：

  (1-Benzenesulfonyl-1H-indol-3-yl)-(3,4,5-trimethoxy-phenyl)-methanol 在 重铬酸吡啶 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 生成 [1-(benzenesulfonyl)indol-3-yl]-(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  4- and 5-Aroylindoles as Novel Classes of Potent Antitubulin Agents

  摘要：

  A novel series of 4- and 5-aroylindole derivatives was prepared and evaluated for antitumor activity. Several compounds showed excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 13, 14, 15, and 18, with IC50 values of 1.9, 1.1, 1.2, and 1.8 mu M, respectively, exhibited more potent inhibition of tubulin polymerization than colchicine. They also displayed antiproliferative activity, with IC50 values ranging from 10 to 43 nM in a variety of human cell lines from different organs.

  DOI：

  10.1021/jm070557q