N'-(7-chloro-quinolin-4-yl)-N-[3-(10,11-dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-N-methyl-propane-1,3-diamine

• 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: N'-(7-chloro-quinolin-4-yl)-N-[3-(10,11-dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-N-methyl-propane-1,3-diamine
• 英文别名: N-(7-chloro-4-quinolyl)-N'-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl]-N'-methyl-propane-1,3-diamine；N-(7-chloroquinolin-4-yl)-N'-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl]-N'-methylpropane-1,3-diamine
• 化学式: C₃₀H₃₃ClN₄
• 分子量: 485.072
• InChiKey: PDWQYJAOQFZCCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  3-[(7-chloroquinolin-4-yl)amino]propan-1-ol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 72.75h， 生成 N'-(7-chloro-quinolin-4-yl)-N-[3-(10,11-dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-N-methyl-propane-1,3-diamine
  参考文献：
  名称：

  A Chloroquine-like Molecule Designed to Reverse Resistance in Plasmodium falciparum

  摘要：

  A class of hybrid molecules which we term 'reversed chloroquines' (RCQs) was designed, and a prototype molecule, N'-(7-chloroquinolin-4-yl)-N-[3-(10,11-dihydrodibenzo[b, f] azepin-5-yl)propyl]-N-methylpropane1,3- diamine ( 1), was synthesized and tested against both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum. An in vitro assay against the two strains indicated that 1 was effective at low-nM concentrations against both strains. A preliminary study in mice demonstrated oral efficacy against P. chabaudi and the absence of obvious toxicity. The RCQ approach therefore appears to be feasible.

  DOI：

  10.1021/jm060399n

文献信息

• WO2006/88541
  申请人：——

  公开号：——

  公开（公告）日：——
• 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