(3-Chlorophenyl)-[4-[[3-[4-[3-[(7-chloroquinolin-4-yl)amino]propyl]piperazin-1-yl]propylamino]methyl]phenyl]methanol | 946005-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-Chlorophenyl)-[4-[[3-[4-[3-[(7-chloroquinolin-4-yl)amino]propyl]piperazin-1-yl]propylamino]methyl]phenyl]methanol
• CAS: 946005-80-7；946005-88-5
• 化学式: C₃₃H₃₉Cl₂N₅O
• 分子量: 592.612
• InChiKey: WVCOKTAARUVNSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.7
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3-Chlorophenyl)-[4-[[3-[4-[3-[(7-chloroquinolin-4-yl)amino]propyl]piperazin-1-yl]propylamino]methyl]phenyl]methanol 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到[(3-Chlorophenyl)-[4-[[3-[4-[3-[(7-chloroquinolin-4-yl)amino]propyl]piperazin-1-yl]propylamino]methyl]phenyl]methyl] methanesulfonate
  参考文献：
  名称：

  Development of piperazine-tethered heterodimers as potent antimalarials against chloroquine-resistant P. falciparum strains. Synthesis and molecular modeling

  摘要：

  The design, synthesis, and antiplasmodial activity of antimalarial heterodimers based on the 1,4-bis(3-aminopropyl)piperazine linker is reported. In this series key structural elements derived from quinoline antimalarials were coupled to fragments capable of coordinating metal ions. Biological evaluation included determination of activity against chloroquine-sensitive and chloroquine-resistant Plasmodiunifaleiparum strains. Some of the novel compounds presented high activity in vitro against chloroquine-resistant strains, more potent than chloroquine and clotrimazole. Computational studies revealed that the activity is likely due to the ability of the compounds to assume a multisite iron coordinating geometry. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.077
• 作为产物：
  描述：

  (4-bromomethyl-phenyl)(3-chloro-phenyl)methanone 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 20.0h， 生成 (3-Chlorophenyl)-[4-[[3-[4-[3-[(7-chloroquinolin-4-yl)amino]propyl]piperazin-1-yl]propylamino]methyl]phenyl]methanol
  参考文献：
  名称：

  Development of piperazine-tethered heterodimers as potent antimalarials against chloroquine-resistant P. falciparum strains. Synthesis and molecular modeling

  摘要：

  The design, synthesis, and antiplasmodial activity of antimalarial heterodimers based on the 1,4-bis(3-aminopropyl)piperazine linker is reported. In this series key structural elements derived from quinoline antimalarials were coupled to fragments capable of coordinating metal ions. Biological evaluation included determination of activity against chloroquine-sensitive and chloroquine-resistant Plasmodiunifaleiparum strains. Some of the novel compounds presented high activity in vitro against chloroquine-resistant strains, more potent than chloroquine and clotrimazole. Computational studies revealed that the activity is likely due to the ability of the compounds to assume a multisite iron coordinating geometry. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.077

文献信息

• Development of piperazine-tethered heterodimers as potent antimalarials against chloroquine-resistant P. falciparum strains. Synthesis and molecular modeling
  作者：Sandra Gemma、Gagan Kukreja、Giuseppe Campiani、Stefania Butini、Matteo Bernetti、Bhupendra P. Joshi、Luisa Savini、Nicoletta Basilico、Donatella Taramelli、Vanessa Yardley、Alessia Bertamino、Ettore Novellino、Marco Persico、Bruno Catalanotti、Caterina Fattorusso

  DOI：10.1016/j.bmcl.2007.04.077

  日期：2007.7

  The design, synthesis, and antiplasmodial activity of antimalarial heterodimers based on the 1,4-bis(3-aminopropyl)piperazine linker is reported. In this series key structural elements derived from quinoline antimalarials were coupled to fragments capable of coordinating metal ions. Biological evaluation included determination of activity against chloroquine-sensitive and chloroquine-resistant Plasmodiunifaleiparum strains. Some of the novel compounds presented high activity in vitro against chloroquine-resistant strains, more potent than chloroquine and clotrimazole. Computational studies revealed that the activity is likely due to the ability of the compounds to assume a multisite iron coordinating geometry. (c) 2007 Elsevier Ltd. All rights reserved.