2-[(7-chloroquinolin-4-yl)amino]butan-1-ol | 1145669-35-7

• 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: 2-[(7-chloroquinolin-4-yl)amino]butan-1-ol
• 英文别名: 2-[(7-Chloro-4-quinolyl)amino]butan-1-ol
• CAS: 1145669-35-7
• 化学式: C₁₃H₁₅ClN₂O
• mdl: MFCD12415526
• 分子量: 250.728
• InChiKey: UFKGWJPAZPGWKN-UHFFFAOYSA-N

物化性质

• 熔点：
  196-198 °C
• 沸点：
  437.8±35.0 °C(predicted)
• 密度：
  1.281±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(7-chloroquinolin-4-yl)amino]butan-1-ol 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到7-chloro-N-[1-(chloromethyl)propyl]quinolin-4-amine
  参考文献：
  名称：

  一系列喹啉衍生物的合成及其体外抗结核活性

  摘要：

  合成了一系列33种喹啉衍生物，并使用Alamar Blue药敏试验评估了其对结核分枝杆菌H 37 Rv的体外抗菌活性，并以μg/ mL的最低抑菌浓度（MIC）表示了该活性。与一线药物（如乙胺丁醇）相比，化合物5e和5f分别在6.25和3.12μg/ mL处显示出显着活性，并且可能是开发新的抗多种药物耐药性先导化合物的良好起点。

  DOI：

  10.1016/j.bmc.2009.01.013
• 作为产物：
  描述：

  2-氨基-1-丁醇 、 4,7-二氯喹啉 以 neat (no solvent) 为溶剂， 反应 24.0h， 以86%的产率得到2-[(7-chloroquinolin-4-yl)amino]butan-1-ol
  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

• N'Da, David D.; Breytenbach, Jaco C.; Smith, Peter J., Arzneimittel-Forschung/Drug Research, 2011, vol. 61, # 6, p. 358 - 365
  作者：N'Da, David D.、Breytenbach, Jaco C.、Smith, Peter J.、Lategan, Carmen

  DOI：——

  日期：——
• Synthesis and in vitro antitubercular activity of a series of quinoline derivatives
  作者：Marcus V.N. de Souza、Karla C. Pais、Carlos R. Kaiser、Mônica A. Peralta、Marcelle de L. Ferreira、Maria C.S. Lourenço

  DOI：10.1016/j.bmc.2009.01.013

  日期：2009.2

  A series of 33 quinoline derivatives have been synthesized and evaluated for their in vitro antibacterial activity against Mycobacterium tuberculosis H37Rv using the Alamar Blue susceptibility test and the activity expressed as the minimum inhibitory concentration (MIC) in μg/mL. Compounds 5e and 5f exhibited a significant activity at 6.25 and 3.12 μg/mL, respectively, when compared with first line

  合成了一系列33种喹啉衍生物，并使用Alamar Blue药敏试验评估了其对结核分枝杆菌H 37 Rv的体外抗菌活性，并以μg/ mL的最低抑菌浓度（MIC）表示了该活性。与一线药物（如乙胺丁醇）相比，化合物5e和5f分别在6.25和3.12μg/ mL处显示出显着活性，并且可能是开发新的抗多种药物耐药性先导化合物的良好起点。
• 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.