7-chloro-N-(3-(4-methylpiperazin-1-yl)propyl)quinolin-4-amine | 1246746-68-8

• 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: 7-chloro-N-(3-(4-methylpiperazin-1-yl)propyl)quinolin-4-amine
• 英文别名: 7-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]quinolin-4-amine
• CAS: 1246746-68-8
• 化学式: C₁₇H₂₃ClN₄
• 分子量: 318.849
• InChiKey: BXOBWXKRYBWTBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  31.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-[(7-chloroquinolin-4-yl)amino]propan-1-ol 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 7-chloro-N-(3-(4-methylpiperazin-1-yl)propyl)quinolin-4-amine
  参考文献：
  名称：

  New derivatives of 7-chloroquinolin-4-amine with antiprotozoal activity

  摘要：

  Novel co-aminoacyl and -alkyl derivatives of 7-chloroquinolin-4-amine were prepared and their structures confirmed by NMR spectroscopy. Their antiprotozoal activities were examined in vitro against the sensitive NF54 strain as well as against the multiresistant K-1 strain of Plasmodium falciparum and against Trypanosoma brucei rhodesiense (STIB 900). The results were compared with the activities of clinically used drugs. Their antitypanosomal activities were only moderate whereas their antiplasmodial activities looked very promising. Some were equal or slightly more active than chloroquine against the sensitive strain. However, in comparison to chloroquine, the activity of the new compounds was decreased much less in the resistant strain. Several possessed activity against both strains in low nanomolar concentration. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.12.006

文献信息

• Synthesis and Evaluation of Chirally Defined Side Chain Variants of 7-Chloro-4-Aminoquinoline To Overcome Drug Resistance in Malaria Chemotherapy
  作者：Vasantha Rao Dola、Awakash Soni、Pooja Agarwal、Hafsa Ahmad、Kanumuri Siva Rama Raju、Mamunur Rashid、Muhammad Wahajuddin、Kumkum Srivastava、W. Haq、A. K. Dwivedi、S. K. Puri、S. B. Katti

  DOI：10.1128/aac.01152-16

  日期：2017.3

  A novel 4-aminoquinoline derivative [( S )-7-chloro- N -(4-methyl-1-(4-methylpiperazin-1-yl)pentan-2-yl)-quinolin-4-amine triphosphate] exhibiting curative activity against chloroquine-resistant malaria parasites has been identified for preclinical development as a blood schizonticidal agent. The lead molecule selected after detailed structure-activity relationship (SAR) studies has good solid-state properties and promising activity against in vitro and in vivo experimental malaria models. The in vitro absorption, distribution, metabolism, and excretion (ADME) parameters indicate a favorable drug-like profile.

  摘要 一种新型 4-氨基喹啉衍生物 [( S )-7-氯- N -(4-甲基-1-(4-甲基哌嗪-1-基)戊烷-2-基)-喹啉-4-胺三磷酸酯]对耐氯喹的疟原虫具有治疗活性，已被确定作为血吸虫杀灭剂进行临床前开发。经过详细的结构-活性关系（SAR）研究后选出的先导分子具有良好的固态特性，对 体外 和 体内 实验疟疾模型具有良好的活性。体外 体外 吸收、分布、代谢和排泄（ADME）参数表明其具有良好的类药物特征。
• Design and synthesis of chloroquine analogs with anti-breast cancer property
  作者：V.R. Solomon、Changkun Hu、Hoyun Lee

  DOI：10.1016/j.ejmech.2010.05.046

  日期：2010.9

  A series of chloroquine (CQ) analogs were designed and synthesized in a repositioning approach to develop compounds with high anti-breast cancer property. The compounds were then examined for their antiproliferative effects on two human breast tumor cell lines and a matching non-cancer cell line. Although many of them showed substantial antiproliferative effects on breast cancer cells examined, two compounds, 7-chloro-N-(3-(4-(7-(trifluoromethyl)quinolin-4-yl)piperazin-1-yl)propyl)quinolin-4-amine (14) and (3[4-(7-chloro-quinolin-4-yl)-piperazin-1-yl]-propyl)-(7-trifluoromethyl-quinolin-4-yl)-amine (26), emerged as the most active among this series. They were particularly potent against MCF7 cells when compared to CQ and cisplatin, a widely prescribed anti-cancer drug. The results suggest that these CQ analogs could serve as bases for the development of a new group of effective cancer chemotherapeutics. (C) 2010 Elsevier Masson SAS. All rights reserved.
• New derivatives of 7-chloroquinolin-4-amine with antiprotozoal activity
  作者：Johanna Faist、Clemens Hinteregger、Werner Seebacher、Robert Saf、Pascal Mäser、Marcel Kaiser、Robert Weis

  DOI：10.1016/j.bmc.2016.12.006

  日期：2017.2

  Novel co-aminoacyl and -alkyl derivatives of 7-chloroquinolin-4-amine were prepared and their structures confirmed by NMR spectroscopy. Their antiprotozoal activities were examined in vitro against the sensitive NF54 strain as well as against the multiresistant K-1 strain of Plasmodium falciparum and against Trypanosoma brucei rhodesiense (STIB 900). The results were compared with the activities of clinically used drugs. Their antitypanosomal activities were only moderate whereas their antiplasmodial activities looked very promising. Some were equal or slightly more active than chloroquine against the sensitive strain. However, in comparison to chloroquine, the activity of the new compounds was decreased much less in the resistant strain. Several possessed activity against both strains in low nanomolar concentration. (C) 2016 Elsevier Ltd. All rights reserved.