1-{4-[4-(7-chloro-quinolin-4-yl)-piperazin-1-yl]-but-2-ynyl}-5-methyl-1H-indole-2,3-dione | 1575882-14-2

• 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: 1-{4-[4-(7-chloro-quinolin-4-yl)-piperazin-1-yl]-but-2-ynyl}-5-methyl-1H-indole-2,3-dione
• 英文别名: 1-{4-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]but-2-ynyl}-5-methyl-1H-indole-2,3-dione；1-[4-[4-(7-Chloro-4-quinolyl)piperazin-1-yl]but-2-ynyl]-5-methyl-indoline-2,3-dione；1-[4-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]but-2-ynyl]-5-methylindole-2,3-dione
• CAS: 1575882-14-2
• 化学式: C₂₆H₂₃ClN₄O₂
• 分子量: 458.947
• InChiKey: WDLADNBZTHMHFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,7-二氯喹啉 在 三乙胺 、 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 1-{4-[4-(7-chloro-quinolin-4-yl)-piperazin-1-yl]-but-2-ynyl}-5-methyl-1H-indole-2,3-dione
  参考文献：
  名称：

  7-氯喹啉-isatin缀合物：抗疟疾，抗结核和细胞毒性评估

  摘要：

  通过直接亲核取代或Cu（II）Cl介导的曼尼希反应，已经合成了一系列二十个由哌嗪拴系的7-氯喹啉-依斯丁杂种。分别评估了这些新的缀合物对恶性疟原虫和结核分枝杆菌的氯喹耐药菌株的抗疟和抗结核功效，同时针对永久性小鼠胚胎成纤维细胞系3T6细胞系评估了细胞毒性谱。最有效的带IC的试验化合物50 0.22  μ米针对W2株恶性疟原虫和31.62  μ米 针对胚胎成纤维细胞的细胞系（细胞毒性）显示出较高的选择性指数143.73。

  DOI：

  10.1111/cbdd.12273

文献信息

• 7-Chloroquinoline-isatin Conjugates: Antimalarial, Antitubercular, and Cytotoxic Evaluation
  作者：Raghu Raj、Christophe Biot、Séverine Carrère-Kremer、Laurent Kremer、Yann Guérardel、Jiri Gut、Philip J. Rosenthal、Delphine Forge、Vipan Kumar

  DOI：10.1111/cbdd.12273

  日期：2014.5

  7‐chloroquinoline–isatin hybrids have been synthesized via either direct nucleophilic substitution or Cu(Ι)Cl‐mediated Mannich reaction. These new conjugates were evaluated for their antimalarial and antitubercular efficacy against a chloroquine‐resistant strain of Plasmodium falciparum and Mycobacterium tuberculosis, respectively, while the cytotoxic profiles were evaluated against 3T6 cell line, a permanent

  通过直接亲核取代或Cu（II）Cl介导的曼尼希反应，已经合成了一系列二十个由哌嗪拴系的7-氯喹啉-依斯丁杂种。分别评估了这些新的缀合物对恶性疟原虫和结核分枝杆菌的氯喹耐药菌株的抗疟和抗结核功效，同时针对永久性小鼠胚胎成纤维细胞系3T6细胞系评估了细胞毒性谱。最有效的带IC的试验化合物50 0.22  μ米针对W2株恶性疟原虫和31.62  μ米 针对胚胎成纤维细胞的细胞系（细胞毒性）显示出较高的选择性指数143.73。
• Cu(I)Cl-promoted synthesis of novel N-alkylated isatin analogs with an extension toward isatin-4-aminoquinoline conjugates: in vitro analysis against Trichomonas vaginalis
  作者：Nisha、Richard Tran、Donald Yang、Dominique Hall、Melissa J. Hopper、Lisa A. Wrischnik、Kirkwood M. Land、Vipan Kumar

  DOI：10.1007/s00044-014-1024-y

  日期：2014.10

  Trichomonas vaginalis, the causative agent of trichomonosis, is the most common non-viral sexually transmitted disease. Infection with this protozoan may have serious consequences, especially for women. Currently, 5-nitroimidazole drugs are the treatment of choice for trichomonosis, but the emergence of drug resistant isolates has limited the effectiveness of this therapy. In this context, a library of isatin-mannich adducts and 4-aminoquinoline-isatin mannich conjugates was synthesized following the Cu-promoted Mannich reaction and evaluated for their preliminary in vitro analysis against T. vaginalis at 50 mu M. The preliminary evaluation data revealed that the introduction of 4-aminoquinoline ring enhanced the activity profiles with compounds viz. 6a and 6c exhibiting percentage growth inhibition of 92.13 and 100 %, respectively. Compounds with high levels of potency were further analyzed to determine their IC50 values as well as cytotoxicity profiles against mammalian cells. The most active compound in the synthesized conjugates displayed an IC50 value of 23 mu M against cultured G3 strain in TYM Diamond's media of T. vaginalis and was non-toxic to cultured mammalian HeLa cells at the same concentration.
• N-Propargylated isatin-Mannich mono- and bis-adducts: Synthesis and preliminary analysis of in vitro activity against Tritrichomonas foetus
  作者：Nisha、Kewal Kumar、Gaurav Bhargava、Kirkwood M. Land、Kai-Hsiang Chang、Reena Arora、Somdutta Sen、Vipan Kumar

  DOI：10.1016/j.ejmech.2014.01.015

  日期：2014.3

  Cu(I)Cl promoted synthesis of N-propargylated-isatin Mannich mono- and bis-adducts with an extension towards the synthesis of N-propargylated-isatin-7-chloroquinoline conjugates was described. The synthesized scaffolds were evaluated for their in vitro activity against the veterinary protozoal pathogen Tritrichomonas foetus and cytotoxicity against human prostate (PC-3) cancer cell line. The preliminary evaluation data revealed the enhancement in the activity profiles with the introduction of 7-chloroquinoline ring with the most active conjugates 7a, 7c and 7d exhibiting an IC50 of 22.2, 11.3 and 24.5 mu M respectively against T. foetus and minimal toxicity against human prostate (PC-3) cell lines. (C) 2014 Elsevier Masson SAS. All rights reserved.