N1-(7-chloroquinolin-4-yl)-N2-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-N2-methylethane-1,2-diamine | 907193-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: N1-(7-chloroquinolin-4-yl)-N2-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-N2-methylethane-1,2-diamine
• 英文别名: RCQ_33；N-(7-chloro-4-quinolyl)-N'-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl]-N'-methyl-ethane-1,2-diamine；N-(7-chloroquinolin-4-yl)-N'-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl]-N'-methylethane-1,2-diamine
• CAS: 907193-99-1
• 化学式: C₂₉H₃₁ClN₄
• 分子量: 471.045
• InChiKey: KBMRVCQIUUDTCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  31.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-((7-chloroquinolin-4-yl)amino)ethyl methanesulfonate 、 地昔帕明 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以0.42 g的产率得到N1-(7-chloroquinolin-4-yl)-N2-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-N2-methylethane-1,2-diamine
  参考文献：
  名称：

  抗疟逆转氯喹化合物的合成、构效关系和作用模式研究

  摘要：

  我们先前已经证明了“反向氯喹（RCQ）”分子，的氯喹等构成部分和耐药性逆转样部分，可以克服在氯喹抗性的恶性疟原虫（伯吉斯，SJ；塞尔泽，A.；凯利，JX；斯米尔克斯坦，MJ；里斯科，MK；佩顿，卫生署 J. 医学。化学 2006年，49，5623。安德鲁斯，S。伯吉斯，SJ；斯卡尔鲁德，D.；凯利，JX；佩顿，卫生署 J. 医学。化学 2010 , 53 , 916)。在这里，我们对 RCQ 结构的构效关系进行了研究，从而产生了一种具有良好体外和体内抗疟活性的口服活性分子。我们还提供了作用方式的证据，表明 RCQ 分子以类似于氯喹的方式抑制寄生虫消化液泡中血红素的形成。

  DOI：

  10.1021/jm1006484

文献信息

• Quinoline Derivatives And Uses Thereof
  申请人：Peyton David H.

  公开号：US20080188462A1

  公开（公告）日：2008-08-07

  This disclosure provides a new class of compounds referred to as “reversed chloroquines” (RCQs), which are highly effective against CQ R and CQ S malaria parasites. RCQs are hybrid molecules, which include an antimalarial quinoline analog (such as chloroquine) moiety and a CQ R reversal moiety. Exemplary RCQ chemical structures are provided. Also provided are pharmaceutical compositions including the disclosed RCQ compounds, and methods of using such compounds and compositions for the treatment of malaria and inhibition of CQ R or CQ S Plasmodium sp. (such as P. falciparum ).
• QUINOLINE DERIVATIVES AND USES THEREOF
  申请人：PEYTON David H.

  公开号：US20110257160A1

  公开（公告）日：2011-10-20

  This disclosure provides a new class of compounds referred to as “reversed chloroquines” (RCQs), which are highly effective against CQ R and CQ S malaria parasites. RCQs are hybrid molecules, which include an antimalarial quinoline analog (such as chloroquine) moiety and a CQ R reversal moiety. Exemplary RCQ chemical structures are provided. Also provided are pharmaceutical compositions including the disclosed RCQ compounds, and methods of using such compounds and compositions for the treatment of malaria and inhibition of CQ R or CQ S Plasmodium sp. (such as P. falciparum ).
• US7968539B2
  申请人：——

  公开号：US7968539B2

  公开（公告）日：2011-06-28
• US8524739B2
  申请人：——

  公开号：US8524739B2

  公开（公告）日：2013-09-03
• US9493420B2
  申请人：——

  公开号：US9493420B2

  公开（公告）日：2016-11-15