7-(4,5-dihydro-1H-imidazol-2-yl)-3-quinolin-2-yl-3H-thiazolo[5',4':3,4]benzo[1,2-d][1,2,3]triazole | 1189062-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-(4,5-dihydro-1H-imidazol-2-yl)-3-quinolin-2-yl-3H-thiazolo[5',4':3,4]benzo[1,2-d][1,2,3]triazole
• 英文别名: 7-(4,5-dihydro-1H-imidazol-2-yl)-3-quinolin-2-yl-[1,3]thiazolo[5,4-e]benzotriazole
• CAS: 1189062-21-2
• 化学式: C₁₉H₁₃N₇S
• 分子量: 371.425
• InChiKey: IUCYJZCDMMHFCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-quinolin-2-yl-3H-thiazolo[5',4':3,4]benzo[1,2-d][1,2,3]triazole-7-carbonitrile 、 乙二胺 以 乙醇 为溶剂， 反应 2.0h， 以66%的产率得到7-(4,5-dihydro-1H-imidazol-2-yl)-3-quinolin-2-yl-3H-thiazolo[5',4':3,4]benzo[1,2-d][1,2,3]triazole
  参考文献：
  名称：

  Synthesis and antitumoral activity of novel thiazolobenzotriazole, thiazoloindolo[3,2-c]quinoline and quinolinoquinoline derivatives

  摘要：

  The biological evaluation of some novel thiazoloindolo[3,2-c]quinoline, 8-substituted-11H-indolo[3,2-c]quinolines is described. These compounds were obtained via Graebe-Ullmann thermal cyclization from appropriated N-arylated benzotriazoles. 7H-4,7-Diaza-benzo[de]anthracene, a reaction by-product structurally closed to the pyridoacridine skeleton was also identified. All thiazolobenzotriazole intermediates were tested in vitro for their capacity to inhibit the growth of two breast cancer cell lines, MCF-7 and MDA-MB-231. In parallel, the newly synthesized skeletons were evaluated for DNA interaction, topoisomerases' inhibition, and cytotoxicity against HL60 and HL60/MX2 human leukemia cells. Most compounds showed a potent growth inhibitory effect on all the tested cell lines, with IC50 in the mu M range. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.04.012

文献信息

• Synthesis and antitumoral activity of novel thiazolobenzotriazole, thiazoloindolo[3,2-c]quinoline and quinolinoquinoline derivatives
  作者：Anne Beauchard、Alexis Jaunet、Laurence Murillo、Brigitte Baldeyrou、Amélie Lansiaux、Jean-René Chérouvrier、Lisianne Domon、Laurent Picot、Christian Bailly、Thierry Besson

  DOI：10.1016/j.ejmech.2009.04.012

  日期：2009.10

  The biological evaluation of some novel thiazoloindolo[3,2-c]quinoline, 8-substituted-11H-indolo[3,2-c]quinolines is described. These compounds were obtained via Graebe-Ullmann thermal cyclization from appropriated N-arylated benzotriazoles. 7H-4,7-Diaza-benzo[de]anthracene, a reaction by-product structurally closed to the pyridoacridine skeleton was also identified. All thiazolobenzotriazole intermediates were tested in vitro for their capacity to inhibit the growth of two breast cancer cell lines, MCF-7 and MDA-MB-231. In parallel, the newly synthesized skeletons were evaluated for DNA interaction, topoisomerases' inhibition, and cytotoxicity against HL60 and HL60/MX2 human leukemia cells. Most compounds showed a potent growth inhibitory effect on all the tested cell lines, with IC50 in the mu M range. (C) 2009 Elsevier Masson SAS. All rights reserved.