tert-butyl (2S)-2-([3-(4-{3-[(7-chloro-4-quinolyl)amino]propyl}piperazino)propyl]aminocarbonyl)tetrahydro-1H-pyrrole-1-carboxylate | 500929-01-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2S)-2-([3-(4-{3-[(7-chloro-4-quinolyl)amino]propyl}piperazino)propyl]aminocarbonyl)tetrahydro-1H-pyrrole-1-carboxylate
• 英文别名: tert-butyl (2S)-2-[3-[4-[3-[(7-chloroquinolin-4-yl)amino]propyl]piperazin-1-yl]propylcarbamoyl]pyrrolidine-1-carboxylate
• CAS: 500929-01-1
• 化学式: C₂₉H₄₃ClN₆O₃
• 分子量: 559.152
• InChiKey: JKBFYXSIBZYMCW-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  90
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-([3-(4-{3-[(7-chloro-4-quinolyl)amino]propyl}piperazino)propyl]aminocarbonyl)tetrahydro-1H-pyrrole-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以28%的产率得到N²-[3-(4-{3-[(7-chloro-4-quinolyl)amino]propyl}piperazino)propyl]-(2S)-tetrahydro-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Antimalarial Activity of N-(7-Chloro-4-quinolyl)-1,4-bis(3-aminopropyl)piperazine Derivatives

  摘要：

  Three series of monoquinolines consisting of a 1,4-bis(3-aminopropyl)piperazine linker and a large variety of terminal groups were synthesized. Our aim was to prove that in related bisquinoline, it is the second quinoline moiety that is responsible for cytotoxicity and that it is not an absolute requirement for overcoming resistance to chloroquine (CQ). Eleven compounds displayed a higher selectivity index (ratio CC50/IC50 activity) than CQ and one of them cured mice infected by Plasmodium berghei.

  DOI：

  10.1021/jm020960r
• 作为产物：
  描述：

  1,4-双(3-氨基丙基)哌嗪 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 戊醇 为溶剂， 反应 22.0h， 生成 tert-butyl (2S)-2-([3-(4-{3-[(7-chloro-4-quinolyl)amino]propyl}piperazino)propyl]aminocarbonyl)tetrahydro-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Antimalarial Activity of N-(7-Chloro-4-quinolyl)-1,4-bis(3-aminopropyl)piperazine Derivatives

  摘要：

  Three series of monoquinolines consisting of a 1,4-bis(3-aminopropyl)piperazine linker and a large variety of terminal groups were synthesized. Our aim was to prove that in related bisquinoline, it is the second quinoline moiety that is responsible for cytotoxicity and that it is not an absolute requirement for overcoming resistance to chloroquine (CQ). Eleven compounds displayed a higher selectivity index (ratio CC50/IC50 activity) than CQ and one of them cured mice infected by Plasmodium berghei.

  DOI：

  10.1021/jm020960r

文献信息

• Synthesis and in Vitro and in Vivo Antimalarial Activity of N-(7-Chloro-4-quinolyl)-1,4-bis(3-aminopropyl)piperazine Derivatives
  作者：Adina Ryckebusch、Rébecca Deprez-Poulain、Louis Maes、Marie-Ange Debreu-Fontaine、Elisabeth Mouray、Philippe Grellier、Christian Sergheraert

  DOI：10.1021/jm020960r

  日期：2003.2.1

  Three series of monoquinolines consisting of a 1,4-bis(3-aminopropyl)piperazine linker and a large variety of terminal groups were synthesized. Our aim was to prove that in related bisquinoline, it is the second quinoline moiety that is responsible for cytotoxicity and that it is not an absolute requirement for overcoming resistance to chloroquine (CQ). Eleven compounds displayed a higher selectivity index (ratio CC50/IC50 activity) than CQ and one of them cured mice infected by Plasmodium berghei.