6-chloro-1-[4-(7-trifluoromethyl-quinolin-4-yl)-piperazin-1-ylmethyl]-1H-indole-2,3-dione | 1218813-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-chloro-1-[4-(7-trifluoromethyl-quinolin-4-yl)-piperazin-1-ylmethyl]-1H-indole-2,3-dione
• 英文别名: 6-Chloro-1-[[4-[7-(trifluoromethyl)quinolin-4-yl]piperazin-1-yl]methyl]indole-2,3-dione
• CAS: 1218813-05-8
• 化学式: C₂₃H₁₈ClF₃N₄O₂
• 分子量: 474.87
• InChiKey: ISAFSRRYTLGINY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-chloro-1-[4-(7-trifluoromethyl-quinolin-4-yl)-piperazin-1-ylmethyl]-1H-indole-2,3-dione 、 氨基硫脲 以 乙醇 为溶剂， 反应 3.0h， 生成 N1-[4-(7-trifluoromethyl-quinolin-4-yl)-piperazin-1-yl]methyl-6-chloro-1H-indole-2,3-dione-3-thiosemicarbazone
  参考文献：
  名称：

  Design and synthesis of anti-breast cancer agents from 4-piperazinylquinoline: A hybrid pharmacophore approach

  摘要：

  A novel class of 4-piperazinylquinoline derivatives based on the isatin scaffold were designed by molecular hybridization approach and synthesized for biological evaluation. Subsequently, the compounds were examined for their cytotoxic effects on two human breast tumor cell lines, MDA-MB468 and MCF7, and two non-cancer breast epithelial cell lines, 184B5 and MCF10A. Although all compounds examined were quite effective on the breast cancer cell lines examined, the compound 4-bromo-1-[4(7-chloro-quinolin-4-yl)-piperazin-1-ylmethyl]-1H-indole-2,3-dione (5b) and N-1-[4-(7-trifluoromethylquinolin4-yl)]-piperazin-1-ylmethyl-4-chloro-1H-indole-2,3-dione-3-thiosemicarbazone (8a) emerged as the most active among this series. It appeared that both 5b and 8a caused apoptosis to MCF7 cancer cells, but not MCF10A non-cancer cells. Thus, 4-piperazinylquinoline linked isatin analog can serve as the prototype molecule for further development of a new class of anti-breast cancer agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.001
• 作为产物：
  描述：

  聚合甲醛 、 6-氯靛红 、 4-(piperazin-1-yl)-7-(trifluoromethyl)quinoline 以 乙醇 、 水 为溶剂， 反应 4.0h， 以58%的产率得到6-chloro-1-[4-(7-trifluoromethyl-quinolin-4-yl)-piperazin-1-ylmethyl]-1H-indole-2,3-dione
  参考文献：
  名称：

  Design and synthesis of anti-breast cancer agents from 4-piperazinylquinoline: A hybrid pharmacophore approach

  摘要：

  A novel class of 4-piperazinylquinoline derivatives based on the isatin scaffold were designed by molecular hybridization approach and synthesized for biological evaluation. Subsequently, the compounds were examined for their cytotoxic effects on two human breast tumor cell lines, MDA-MB468 and MCF7, and two non-cancer breast epithelial cell lines, 184B5 and MCF10A. Although all compounds examined were quite effective on the breast cancer cell lines examined, the compound 4-bromo-1-[4(7-chloro-quinolin-4-yl)-piperazin-1-ylmethyl]-1H-indole-2,3-dione (5b) and N-1-[4-(7-trifluoromethylquinolin4-yl)]-piperazin-1-ylmethyl-4-chloro-1H-indole-2,3-dione-3-thiosemicarbazone (8a) emerged as the most active among this series. It appeared that both 5b and 8a caused apoptosis to MCF7 cancer cells, but not MCF10A non-cancer cells. Thus, 4-piperazinylquinoline linked isatin analog can serve as the prototype molecule for further development of a new class of anti-breast cancer agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.001

文献信息

• Design and synthesis of anti-breast cancer agents from 4-piperazinylquinoline: A hybrid pharmacophore approach
  作者：V. Raja Solomon、Changkun Hu、Hoyun Lee

  DOI：10.1016/j.bmc.2010.01.001

  日期：2010.2

  A novel class of 4-piperazinylquinoline derivatives based on the isatin scaffold were designed by molecular hybridization approach and synthesized for biological evaluation. Subsequently, the compounds were examined for their cytotoxic effects on two human breast tumor cell lines, MDA-MB468 and MCF7, and two non-cancer breast epithelial cell lines, 184B5 and MCF10A. Although all compounds examined were quite effective on the breast cancer cell lines examined, the compound 4-bromo-1-[4(7-chloro-quinolin-4-yl)-piperazin-1-ylmethyl]-1H-indole-2,3-dione (5b) and N-1-[4-(7-trifluoromethylquinolin4-yl)]-piperazin-1-ylmethyl-4-chloro-1H-indole-2,3-dione-3-thiosemicarbazone (8a) emerged as the most active among this series. It appeared that both 5b and 8a caused apoptosis to MCF7 cancer cells, but not MCF10A non-cancer cells. Thus, 4-piperazinylquinoline linked isatin analog can serve as the prototype molecule for further development of a new class of anti-breast cancer agents. (C) 2010 Elsevier Ltd. All rights reserved.