3-(3,4,5-trimethoxybenzoyl)-1,7-dicyanoindolizine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3,4,5-trimethoxybenzoyl)-1,7-dicyanoindolizine
• 英文别名: 3-(3,4,5-Trimethoxybenzoyl)indolizine-1,7-dicarbonitrile；3-(3,4,5-trimethoxybenzoyl)indolizine-1,7-dicarbonitrile
• 化学式: C₂₀H₁₅N₃O₄
• 分子量: 361.357
• InChiKey: SHQFKVOQPYABQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  96.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-溴-1-(3,4,5-三甲氧基苯基)乙酮 在 三乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 28.0h， 生成 3-(3,4,5-trimethoxybenzoyl)-1,7-dicyanoindolizine
  参考文献：
  名称：

  Studies on indolizines. Evaluation of their biological properties as microtubule-interacting agents and as melanoma targeting compounds

  摘要：

  With the aim of investigating new analogues of phenstatin with an indolizin-3-yl unit, in particular as the B-ring, three new series of compounds (6-8, 9-34 and 54) were synthesized and tested for interactions with tubulin polymerization and evaluated for cytotoxicity on an NCI-60 human cancer cell lines panel. The replacement of the 3'-hydroxy-4'-methoxyphenyl B-ring of phenstatin with substituted indolizine unit results in the conservation of both antitubulin and cytotoxic effect. Indolizines 9 and 17 were the most effective in the present study and showed the highest antiproliferative effect on melanoma cell lines MDA-MB-435 (GI(50) = 30 nM) and could serve as new lead compounds for the development of anti-cancer therapeutics. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.041