N-[{2-(N-benzyl-N-methylaminomethyl)phenyl}methyl]-7-chloro-4-quinolinamine | 1207535-37-2

• 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-[{2-(N-benzyl-N-methylaminomethyl)phenyl}methyl]-7-chloro-4-quinolinamine
• 英文别名: VZ1；N-[{2-(N-benzyI-N-methylaminomethyI)phenyl}methyl]-7-chIoro-4-quinolinamine；N-[[2-[[benzyl(methyl)amino]methyl]phenyl]methyl]-7-chloro-quinolin-4-amine；N-[[2-[[benzyl(methyl)amino]methyl]phenyl]methyl]-7-chloroquinolin-4-amine
• CAS: 1207535-37-2
• 化学式: C₂₅H₂₄ClN₃
• 分子量: 401.939
• InChiKey: KCCAYCIGOLFFDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,7-二氯喹啉 、 o-[(N-benzyl-N-methyl)aminomethyl]benzylamine 在 potassium carbonate 、 三乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 48.0h， 以37%的产率得到N-[{2-(N-benzyl-N-methylaminomethyl)phenyl}methyl]-7-chloro-4-quinolinamine
  参考文献：
  名称：

  [EN] QUINOLINE COMPOUNDS CONTAINING A DIBEMETHIN GROUP
  [FR] COMPOSÉS DE QUINOLÉINE CONTENANT UN GROUPE DIBÉMÉTHINE

  摘要：

  公开号：

  WO2010018555A4

文献信息

• [EN] QUINOLINE COMPOUNDS CONTAINING A DIBEMETHIN GROUP<br/>[FR] COMPOSÉS DE QUINOLÉINE CONTENANT UN GROUPE DIBÉMÉTHINE
  申请人：UNIV CAPE TOWN

  公开号：WO2010018555A4

  公开（公告）日：2010-09-10
• Quinoline Antimalarials Containing a Dibemethin Group Are Active against Chloroquinone-Resistant <i>Plasmodium falciparum</i> and Inhibit Chloroquine Transport via the <i>P. falciparum</i> Chloroquine-Resistance Transporter (PfCRT)
  作者：Vincent K. Zishiri、Mukesh C. Joshi、Roger Hunter、Kelly Chibale、Peter J. Smith、Robert L. Summers、Rowena E. Martin、Timothy J. Egan

  DOI：10.1021/jm2009698

  日期：2011.10.13

  A series of 4-amino-7-chloroquinolines with dibenzylmethylamine (dibemethin) side chains were shown to inhibit synthetic hemozoin formation. These compounds were equally active against cultures of chloroquine-sensitive (D10) and chloroquine-resistant (K1) Plasmodium falciparum. The most active compound had an IC50 value comparable to that of chloroquine, and its potency was undiminished when tested in three additional chloroquine-resistant strains. The three most active compounds exhibited little or no cytotoxicity in a mammalian cell line. When tested in vivo against mouse malaria via oral administration, two of the dibemethin derivatives reduced parasitemia by over 99%, with mice treated at 100 mg/kg surviving the full length of the experiment. Three of the compounds were also shown to inhibit chloroquine transport via the parasite's chloroquine-resistance transporter (PfCRT) in a Xenopus oocyte expression system. This constitutes the first example of a dual-function antimalarial for which the ability to inhibit both hemozoin formation and PfCRT has been demonstrated directly.