N4-[3-(4-{3-[(cyclopropylmethyl)amino]propyl}piperazino)propyl]-7-chloroquinolin-4-amine | 500929-80-6

• 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-[(cyclopropylmethyl)amino]propyl}piperazino)propyl]-7-chloroquinolin-4-amine
• 英文别名: 7-chloro-N-[3-[4-[3-(cyclopropylmethylamino)propyl]piperazin-1-yl]propyl]quinolin-4-amine
• CAS: 500929-80-6
• 化学式: C₂₃H₃₄ClN₅
• 分子量: 416.009
• InChiKey: ZQXLIQFZQAOZAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  4.0
• 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-[(cyclopropylmethyl)amino]propyl}piperazino)propyl]-7-chloroquinolin-4-amine 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 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 3-Amino-N-(3-{4-[3-(7-chloro-quinolin-4-ylamino)-propyl]-piperazin-1-yl}-propyl)-N-cyclopropylmethyl-propionamide
  参考文献：
  名称：

  Synthesis and antimalarial evaluation of new N1-(7-chloro-4-quinolyl)-1,4-bis(3-aminopropyl)piperazine derivatives

  摘要：

  Synthesis and evaluation of the activity of new N-1-(7-chloro-4-quinolyl)-1,4-bis(3-aminopropyl)piperazine derivatives against a chloroquine-resistant strain of Plasmodium falciparum are described. Selectivity indices were improved for two compounds versus the lead 1, the bis-cyclopropylmethyl derivative, thus increasing the therapeutic interest of our family. As our previous studies conducted on the mode of action of our compounds made us hypothesize the existence of original mechanisms and/or original targets, terminal amino derivatives can be considered as promising tools further mechanistical studies, as probes for affinity chromatography. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.080
• 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-[(cyclopropylmethyl)amino]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：——
• Similar Structure−Activity Relationships of Quinoline Derivatives for Antiprion and Antimalarial Effects
  作者：Ralf Klingenstein、Patricia Melnyk、S. Rutger Leliveld、Adina Ryckebusch、Carsten Korth

  DOI：10.1021/jm0602763

  日期：2006.8.1

  Prion diseases are invariably fatal neurodegenerative diseases, in which the infectious agent consists of PrPSc, a pathogenic misfolded isoform of the normal cellular prion protein ( PrPC). Until now, no pharmacological options exist for these novel pathogens. Here we describe the screening of a series of polyquinolines and quinolines linked to a large variety of terminal groups for their ability to cure a persistently prion infected cell line (ScN2a). Several compounds showed antiprion activity in the nanomolar range. The most active molecule, named 42, had a half-effective concentration (EC50) for antiprion activity of 50 nM. In a library of quinoline derivatives we were able to identify several structure-activity relationships (SAR). Remarkably, antiprion SAR in ScN2a cells were similar to antimalarial SAR in a cell model of malaria, particularly for the sulfonamide quinoline derivatives, suggesting that some molecular targets of antiprion and antimalarial substances overlap.
• USE OF 1,4-BIS (3-AMINOALKYL) PIPERAZINE DERIVATIVES IN THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP1809288B1

  公开（公告）日：2011-09-14
• [EN] USE OF 1,4-BIS (3-AMINOALKYL) PIPERAZINE DERIVATIVES IN THE TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] UTILISATION DE DERIVES DE LA 1,4-BIS (3-AMINOALKYL) PIPERAZINE POUR LE TRAITEMENT DE MALADIES NEURODEGENERATIVES
  申请人：EDICALE INSERM INST NAT DE LA

  公开号：WO2006051489A1

  公开（公告）日：2006-05-18

  [EN] 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.
  [FR] L'invention porte sur l'utilisation de dérivés de la 1,4-bis (3-aminoalkyl) pipérazine de formule (I) et (II) pour la fabrication de préparations pharmaceutiques devant servir au traitement de maladies neurodégénératives et de maladies associées, de troubles du développement et du cancer. L'invention porte également sur certains dérivés spécifiques de la 1,4-bis (3-aminoalkyl) pipérazine et sur des préparations pharmaceutiques les contenant.