6-[2-[(7-Chloro-4-quinolyl)amino]butoxy]pyrimidine-2,4-diamine | 1416066-20-0

• 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: 6-[2-[(7-Chloro-4-quinolyl)amino]butoxy]pyrimidine-2,4-diamine
• 英文别名: 6-[2-[(7-chloroquinolin-4-yl)amino]butoxy]pyrimidine-2,4-diamine
• CAS: 1416066-20-0
• 化学式: C₁₇H₁₉ClN₆O
• 分子量: 358.83
• InChiKey: SFJGSGLNUIXGIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,7-二氯喹啉 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 6-[2-[(7-Chloro-4-quinolyl)amino]butoxy]pyrimidine-2,4-diamine
  参考文献：
  名称：

  Synthesis, characterization and antimalarial activity of quinoline–pyrimidine hybrids

  摘要：

  The aim of this study was to synthesize a series of quinoline-pyrimidine hybrids and to evaluate their in vitro antimalarial activity as well as cytotoxicity. The hybrids were brought about in a two-step nucleophilic substitution process involving quinoline and pyrimidine moieties. They were screened alongside chloroquine (CQ), pyrimethamine (PM) and fixed combinations thereof against the D10 and Dd2 strains of Plasmodium falciparum. The cytotoxicity was determined against the mammalian Chinese Hamster Ovarian cell line. The compounds were all active against both strains. However, hybrid (21) featuring piperazine linker stood as the most active of all. It was found as potent as CQ and PM against the D10 strain, and possessed a moderately superior potency over CQ against the Dd2 strain (IC50: 0.157 vs 0.417 mu M, similar to threefold), and also displayed activity comparable to that of the equimolar fixed combination of CQ and PM against both strains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.019

文献信息

• Synthesis, characterization and antimalarial activity of quinoline–pyrimidine hybrids
  作者：Stefan I. Pretorius、Wilma J. Breytenbach、Carmen de Kock、Peter J. Smith、David D. N’Da

  DOI：10.1016/j.bmc.2012.10.019

  日期：2013.1

  The aim of this study was to synthesize a series of quinoline-pyrimidine hybrids and to evaluate their in vitro antimalarial activity as well as cytotoxicity. The hybrids were brought about in a two-step nucleophilic substitution process involving quinoline and pyrimidine moieties. They were screened alongside chloroquine (CQ), pyrimethamine (PM) and fixed combinations thereof against the D10 and Dd2 strains of Plasmodium falciparum. The cytotoxicity was determined against the mammalian Chinese Hamster Ovarian cell line. The compounds were all active against both strains. However, hybrid (21) featuring piperazine linker stood as the most active of all. It was found as potent as CQ and PM against the D10 strain, and possessed a moderately superior potency over CQ against the Dd2 strain (IC50: 0.157 vs 0.417 mu M, similar to threefold), and also displayed activity comparable to that of the equimolar fixed combination of CQ and PM against both strains. (C) 2012 Elsevier Ltd. All rights reserved.