N¹-[4-(7-chloroquinolin-4-yl)piperazin-1-ylmethyl]-5-methyl-1H-indole-2,3-dione | 852401-87-7

• 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: N¹-[4-(7-chloroquinolin-4-yl)piperazin-1-ylmethyl]-5-methyl-1H-indole-2,3-dione
• 英文别名: 1-[[4-(7-chloroquinolin-4-yl)piperazin-1-yl]methyl]-5-methylindole-2,3-dione
• CAS: 852401-87-7
• 化学式: C₂₃H₂₁ClN₄O₂
• 分子量: 420.898
• InChiKey: ZFZXQJWWTDOMRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  56.75
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N¹-[4-(7-chloroquinolin-4-yl)piperazin-1-ylmethyl]-5-methyl-1H-indole-2,3-dione 、 氨基硫脲 反应 3.0h， 以78%的产率得到N¹-[4-(7-chloroquinolin-4-yl)piperazin-1-ylmethyl]-5-methyl-1H-indole-2,3-dione 3-thiosemicarbazone
  参考文献：
  名称：

  Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives

  摘要：

  A new class of 4-aminoquinoline derivatives based on the natural product isatin scaffold were designed and synthesized for biological evaluation against three strains of the malaria parasite Plasmodium falciparum. These derivatives showed anti-plasmodial IC50 values in the ranges of 1.3-0.079 and 2.0-0.050 mu M against a chloroquine-sensitive (D10) and two resistant (K1 and W2) strains of P. falciparum, respectively. In order to determine potential targets for this class of compounds in P. falciparum, selected compounds were also tested against the parasitic cysteine protease falcipain-2. In terms of further development of this class of isatin derivatives, two of the compounds based on a flexible alkyl chain linker and a thiosemicarbazone moiety warrant further investigation as potential anti-plasmodial leads. These two derivatives showed good in vitro activity against K1 and W2 with IC50 values of 51 and 54 nM, respectively, while retaining potency against the D10 strain with IC50 values of 79 and 95 nM, respectively. Generally speaking, the inhibitory potency of all compounds in the series against the parasites did not strongly correlate with inhibitory potency against falcipain-2 for selected compounds tested, which at best was weak to moderate, suggesting other mechanisms of inhibition may also be involved or compounds may be selectively taken up by Plasmodium falciparum. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.037
• 作为产物：
  描述：

  4,7-二氯喹啉 在 potassium carbonate 、 三乙胺 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 水 为溶剂， 反应 7.0h， 生成 N¹-[4-(7-chloroquinolin-4-yl)piperazin-1-ylmethyl]-5-methyl-1H-indole-2,3-dione
  参考文献：
  名称：

  Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives

  摘要：

  A new class of 4-aminoquinoline derivatives based on the natural product isatin scaffold were designed and synthesized for biological evaluation against three strains of the malaria parasite Plasmodium falciparum. These derivatives showed anti-plasmodial IC50 values in the ranges of 1.3-0.079 and 2.0-0.050 mu M against a chloroquine-sensitive (D10) and two resistant (K1 and W2) strains of P. falciparum, respectively. In order to determine potential targets for this class of compounds in P. falciparum, selected compounds were also tested against the parasitic cysteine protease falcipain-2. In terms of further development of this class of isatin derivatives, two of the compounds based on a flexible alkyl chain linker and a thiosemicarbazone moiety warrant further investigation as potential anti-plasmodial leads. These two derivatives showed good in vitro activity against K1 and W2 with IC50 values of 51 and 54 nM, respectively, while retaining potency against the D10 strain with IC50 values of 79 and 95 nM, respectively. Generally speaking, the inhibitory potency of all compounds in the series against the parasites did not strongly correlate with inhibitory potency against falcipain-2 for selected compounds tested, which at best was weak to moderate, suggesting other mechanisms of inhibition may also be involved or compounds may be selectively taken up by Plasmodium falciparum. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.037