N4-[3-(4-{3-(isobutylamino)propyl}piperazino)propyl]-7-chloroquinolin-4-amine | 500930-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N4-[3-(4-{3-(isobutylamino)propyl}piperazino)propyl]-7-chloroquinolin-4-amine
• 英文别名: 7-chloro-N-[3-[4-[3-(2-methylpropylamino)propyl]piperazin-1-yl]propyl]quinolin-4-amine
• CAS: 500930-65-4
• 化学式: C₂₃H₃₆ClN₅
• 分子量: 418.025
• InChiKey: AZDURTUUIQUVHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  43.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N4-[3-(4-{3-(isobutylamino)propyl}piperazino)propyl]-7-chloroquinolin-4-amine 在 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 N-(3-{4-[3-(7-Chloro-quinolin-4-ylamino)-propyl]-piperazin-1-yl}-propyl)-N-isobutyl-malonamic acid
  参考文献：
  名称：

  Design, synthesis and antimalarial activity of novel, quinoline-Based, zinc metallo-aminopeptidase inhibitors

  摘要：

  PfA-M1, a neutral zinc aminopeptidase of Plasmodium falciparum, is a new potential target for the discovery of anti-malarials. The design and synthesis of a library of 45 quinoline-based inhibitors of PfA-M1 is reported. The best inhibitor displays an IC50 of 854 nM. The antimalarial activity on a CQ-resistant strain and the specificity towards mammalian aminopeptidase N are also discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00550-x
• 作为产物：
  描述：

  1,4-双(3-氨基丙基)哌嗪 在 sodium tetrahydroborate 、 3 A molecular sieve 、 TEA 作用下， 以 甲醇 、 戊醇 为溶剂， 反应 22.5h， 生成 N4-[3-(4-{3-(isobutylamino)propyl}piperazino)propyl]-7-chloroquinolin-4-amine
  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

• Use of 1,4-bis (3-aminoalkyl) piperazine derivatives in the treatment of neurodegenerative diseases
  申请人：Sergeant Nicolas

  公开号：US09044478B2

  公开（公告）日：2015-06-02

  Use of 1,4-bis(3-aminoalkyl)piperazine derivatives as defined in formula I or II for the manufacture of a pharmaceutical composition intended for the treatment of neurodegenerative diseases, related neurodegenerative diseases, developmental diseases or cancer. The instant invention is also directed to some specific 1,4-bis(3-aminoalkyl)piperazine derivatives and pharmaceutical composition including them.

  使用公式I或II中定义的1,4-双(3-氨基烷基)哌嗪衍生物制造用于治疗神经退行性疾病、相关神经退行性疾病、发育性疾病或癌症的药物组合物。本发明还涉及一些特定的1,4-双(3-氨基烷基)哌嗪衍生物和包括它们的药物组合物。
• WO2006/51489
  申请人：——

  公开号：——

  公开（公告）日：——
• Design, synthesis and antimalarial activity of novel, quinoline-Based, zinc metallo-aminopeptidase inhibitors
  作者：Marian Flipo、Isabelle Florent、Philippe Grellier、Christian Sergheraert、Rebecca Deprez-Poulain

  DOI：10.1016/s0960-894x(03)00550-x

  日期：2003.8

  PfA-M1, a neutral zinc aminopeptidase of Plasmodium falciparum, is a new potential target for the discovery of anti-malarials. The design and synthesis of a library of 45 quinoline-based inhibitors of PfA-M1 is reported. The best inhibitor displays an IC50 of 854 nM. The antimalarial activity on a CQ-resistant strain and the specificity towards mammalian aminopeptidase N are also discussed. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.