3-[(7-chloroquinolin-4-yl)amino]chloropropane | 337472-81-8

• 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: 3-[(7-chloroquinolin-4-yl)amino]chloropropane
• 英文别名: 7-chloro-N-(3-chloropropyl)quinolin-4-amine
• CAS: 337472-81-8
• 化学式: C₁₂H₁₂Cl₂N₂
• 分子量: 255.147
• InChiKey: SNHOVCPNKMSPEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[(7-chloroquinolin-4-yl)amino]chloropropane 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 (2R,3S)-[(((7-chloroquinolin-4-yl)aminopropyl)-1H-1,2,3-triazol-4-yl)methyl]-3-benzamido-2-hydroxy-3-phenylpropanamide
  参考文献：
  名称：

  Design, Synthesis, and Antiplasmodial Activity of Hybrid Compounds Based on (2R,3S)-N-Benzoyl-3-phenylisoserine

  摘要：

  A series of hybrid compounds based, on.(2R,3S)-N-benzoyl-3-phenylisoserine, artemisinin, and quinoline moieties was synthesized and tested for in vitro antiplasmodial activity against erythrocytic stages of K1 and W2 strains of Plasmodium falciparum Two hybrid compounds incorporating (2R,3S)-N-benzoyl-3-phenylisoserine and artemisinin scaffolds were 3- to 4-fold more active than dihydroartemisinin, with nanomolar IC50 values against Plasmodium falciparum K1 strain.

  DOI：

  10.1021/ml400164t
• 作为产物：
  描述：

  3-[(7-chloroquinolin-4-yl)amino]propan-1-ol 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以96%的产率得到3-[(7-chloroquinolin-4-yl)amino]chloropropane
  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

文献信息

• Synthesis, Antiplasmodial and Antitrypanosomal Evaluation of a Series of Novel 2-Oxoquinoline-based Thiosemicarbazone Derivatives
  作者：Oliver T. Darrel、Siyabonga T. Hulushe、Thanduxolo E. Mtshare、Richard M. Beteck、Michelle Isaacs、Dustin Laming、Heinrich C. Hoppe、Rui W.M. Krause、Setshaba D. Khanye

  DOI：10.17159/0379-4350/2018/v71a23

  日期：——

  Herein a series of novel thiosemicarbazones (TSCs) derived from 2-oxoquinoline scaffold is reported, and the target compounds have been successfully synthesized and characterized using standard spectroscopic techniques. The in vitro biological activities of synthesized molecules were evaluated against Plasmodium falciparum malaria parasites (strain 3D7), Trypanosoma brucei brucei parasites (strain

  本文报道了一系列衍生自2-氧代喹啉骨架的新型硫代半脲（TSC），并已使用标准光谱技术成功合成并表征了目标化合物。评价了合成分子对恶性疟原虫疟原虫（3D7株），布鲁氏锥虫布鲁氏原虫（427株）和HeLa细胞的体外生物学活性。在浓度为20μM时，所有化合物均显示适度或无活性，经常观察到存活率百分数> 50％。除化合物9o外，最终化合物均未对20μM的HeLa细胞表现出细胞毒性作用。
• 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.
• Design, Synthesis, and Antiplasmodial Activity of Hybrid Compounds Based on (2<i>R</i>,3<i>S</i>)-<i>N</i>-Benzoyl-3-phenylisoserine
  作者：Peter M. Njogu、Jiri Gut、Philip J. Rosenthal、Kelly Chibale

  DOI：10.1021/ml400164t

  日期：2013.7.11

  A series of hybrid compounds based, on.(2R,3S)-N-benzoyl-3-phenylisoserine, artemisinin, and quinoline moieties was synthesized and tested for in vitro antiplasmodial activity against erythrocytic stages of K1 and W2 strains of Plasmodium falciparum Two hybrid compounds incorporating (2R,3S)-N-benzoyl-3-phenylisoserine and artemisinin scaffolds were 3- to 4-fold more active than dihydroartemisinin, with nanomolar IC50 values against Plasmodium falciparum K1 strain.
• 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。