N-[6-(7-chloro-quinolin-4-ylamino)-hexyl]-2-(4-formyl-phenoxy)-acetamide

• 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-[6-(7-chloro-quinolin-4-ylamino)-hexyl]-2-(4-formyl-phenoxy)-acetamide
• 英文别名: N-[6-[(7-chloro-4-quinolyl)amino]hexyl]-2-(4-formylphenoxy)acetamide；N-[6-[(7-chloroquinolin-4-yl)amino]hexyl]-2-(4-formylphenoxy)acetamide
• 化学式: C₂₄H₂₆ClN₃O₃
• 分子量: 439.942
• InChiKey: OXJOXZUSTMTDSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[6-(7-chloro-quinolin-4-ylamino)-hexyl]-2-(4-formyl-phenoxy)-acetamide 、 对甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以91%的产率得到N-[6-(7-chloro-quinolin-4-ylamino)-hexyl]-2-{4-[3-(4-methoxy-phenyl)-3-oxo-propenyl]-phenoxy}-acetamide
  参考文献：
  名称：

  Synthesis and in vitro antiplasmodial evaluation of 7-chloroquinoline–chalcone and 7-chloroquinoline–ferrocenylchalcone conjugates

  摘要：

  The manuscript describes the synthesis of novel amide tethered 7-chloroquinoline chalcone and 7-chloroquinoline-ferrocenylchalcone bifunctional hybrids and their evaluation as antimalarial agents against W2 resistant strain of Plasmodium falciparum. The antiplasmodial activity of 7-chloroquinoline-ferrocenylchalcones was found to be less than their corresponding simple chalcone conjugates. The presence of a methoxy substituent at para position of ring B on chalcones and longer alkyl chain length markedly improved the antiplasmodial profiles of the synthesized scaffolds with the most potent of the test compound exhibiting an IC50 value of 17.8 nM. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.045
• 作为产物：
  描述：

  对羟基苯甲醛 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[6-(7-chloro-quinolin-4-ylamino)-hexyl]-2-(4-formyl-phenoxy)-acetamide
  参考文献：
  名称：

  Synthesis and in vitro antiplasmodial evaluation of 7-chloroquinoline–chalcone and 7-chloroquinoline–ferrocenylchalcone conjugates

  摘要：

  The manuscript describes the synthesis of novel amide tethered 7-chloroquinoline chalcone and 7-chloroquinoline-ferrocenylchalcone bifunctional hybrids and their evaluation as antimalarial agents against W2 resistant strain of Plasmodium falciparum. The antiplasmodial activity of 7-chloroquinoline-ferrocenylchalcones was found to be less than their corresponding simple chalcone conjugates. The presence of a methoxy substituent at para position of ring B on chalcones and longer alkyl chain length markedly improved the antiplasmodial profiles of the synthesized scaffolds with the most potent of the test compound exhibiting an IC50 value of 17.8 nM. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.045

文献信息

• Synthesis and in vitro antiplasmodial evaluation of 7-chloroquinoline–chalcone and 7-chloroquinoline–ferrocenylchalcone conjugates
  作者：Raghu Raj、Anu Saini、Jiri Gut、Philip J. Rosenthal、Vipan Kumar

  DOI：10.1016/j.ejmech.2015.03.045

  日期：2015.5

  The manuscript describes the synthesis of novel amide tethered 7-chloroquinoline chalcone and 7-chloroquinoline-ferrocenylchalcone bifunctional hybrids and their evaluation as antimalarial agents against W2 resistant strain of Plasmodium falciparum. The antiplasmodial activity of 7-chloroquinoline-ferrocenylchalcones was found to be less than their corresponding simple chalcone conjugates. The presence of a methoxy substituent at para position of ring B on chalcones and longer alkyl chain length markedly improved the antiplasmodial profiles of the synthesized scaffolds with the most potent of the test compound exhibiting an IC50 value of 17.8 nM. (C) 2015 Elsevier Masson SAS. All rights reserved.