N-(3-(4-methylpiperazin-1-yl)propyl)-7-(trifluoromethyl)quinolin-4-amine | 1246746-78-0

• 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: N-(3-(4-methylpiperazin-1-yl)propyl)-7-(trifluoromethyl)quinolin-4-amine
• 英文别名: [3-(4-methyl-piperazin-1-yl)-propyl]-(7-trifluoromethylquinolin-4-yl)-amine；N-[3-(4-methylpiperazin-1-yl)propyl]-7-(trifluoromethyl)quinolin-4-amine
• CAS: 1246746-78-0
• 化学式: C₁₈H₂₃F₃N₄
• 分子量: 352.403
• InChiKey: ATIUDOXABGEADF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  31.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  benzyl 3-(4-methylpiperazin-1-yl)propylcarbamate 在 palladium 10% on activated carbon 、 氢气 、 苯酚 作用下， 以 甲醇 为溶剂， 20.0~155.0 ℃ 、206.85 kPa 条件下， 反应 1.0h， 生成 N-(3-(4-methylpiperazin-1-yl)propyl)-7-(trifluoromethyl)quinolin-4-amine
  参考文献：
  名称：

  Synthesis and Evaluation of Chirally Defined Side Chain Variants of 7-Chloro-4-Aminoquinoline To Overcome Drug Resistance in Malaria Chemotherapy

  摘要：

  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。

  DOI：

  10.1128/aac.01152-16

文献信息

• 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.
• 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。