(E)-2-sec-butyl-6-((2-(7-chloroquinolin-4-ylamino)ethylamino)methylene)-4-((E)-3-oxo-3-phenylprop-1-enyl)cyclohexa-2,4-dienone | 1375171-23-5

• 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: (E)-2-sec-butyl-6-((2-(7-chloroquinolin-4-ylamino)ethylamino)methylene)-4-((E)-3-oxo-3-phenylprop-1-enyl)cyclohexa-2,4-dienone
• 英文别名: (6E)-2-butan-2-yl-6-[[2-[(7-chloroquinolin-4-yl)amino]ethylamino]methylidene]-4-[(E)-3-oxo-3-phenylprop-1-enyl]cyclohexa-2,4-dien-1-one
• CAS: 1375171-23-5
• 化学式: C₃₁H₃₀ClN₃O₂
• 分子量: 512.051
• InChiKey: MOJGKHGHWNXEPL-CGJUGKPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.09
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-仲丁基苯酚 在 盐酸 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 5.17h， 生成 (E)-2-sec-butyl-6-((2-(7-chloroquinolin-4-ylamino)ethylamino)methylene)-4-((E)-3-oxo-3-phenylprop-1-enyl)cyclohexa-2,4-dienone
  参考文献：
  名称：

  Antiplasmodial activity of novel keto-enamine chalcone-chloroquine based hybrid pharmacophores

  摘要：

  A series of novel keto-enamine chalcone-chloroquine based hybrids were synthesized following new methodology developed in our laboratory. The synthesized compounds were screened against chloroquine sensitive strain (3D7) of Plasmodium falciparum in an in vitro model. Some of the compounds were showing comparable antimalarial activity at par with chloroquine. Compounds with significant in vitro antimalarial activity were then evaluated for their in vivo efficacy in Swiss mice against Plasmodium yoelii (chloroquine resistant N-67 strain), wherein compounds 25 and 27 each showed an in vivo suppression of 99.9% parasitaemia on day 4. Biochemical studies reveal that inhibition of hemozoin formation is the primary mechanism of action of these analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.011

文献信息

• Antiplasmodial activity of novel keto-enamine chalcone-chloroquine based hybrid pharmacophores
  作者：Koneni V. Sashidhara、Manoj Kumar、Ram K. Modukuri、Rajeev Kumar Srivastava、Awakash Soni、Kumkum Srivastava、Shiv Vardan Singh、J.K. Saxena、Harsh M. Gauniyal、Sunil K. Puri

  DOI：10.1016/j.bmc.2012.03.011

  日期：2012.5

  A series of novel keto-enamine chalcone-chloroquine based hybrids were synthesized following new methodology developed in our laboratory. The synthesized compounds were screened against chloroquine sensitive strain (3D7) of Plasmodium falciparum in an in vitro model. Some of the compounds were showing comparable antimalarial activity at par with chloroquine. Compounds with significant in vitro antimalarial activity were then evaluated for their in vivo efficacy in Swiss mice against Plasmodium yoelii (chloroquine resistant N-67 strain), wherein compounds 25 and 27 each showed an in vivo suppression of 99.9% parasitaemia on day 4. Biochemical studies reveal that inhibition of hemozoin formation is the primary mechanism of action of these analogues. (C) 2012 Elsevier Ltd. All rights reserved.