N-[{2-(azidomethyl)phenyl}methyl]-N-(4-dimethylaminobenzyl)methylamine | 1207535-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[{2-(azidomethyl)phenyl}methyl]-N-(4-dimethylaminobenzyl)methylamine
• 英文别名: 4-[[[2-(azidomethyl)phenyl]methyl-methylamino]methyl]-N,N-dimethylaniline
• CAS: 1207535-62-3
• 化学式: C₁₈H₂₃N₅
• 分子量: 309.414
• InChiKey: FDUSNXXMBKGOBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[{2-(azidomethyl)phenyl}methyl]-N-(4-dimethylaminobenzyl)methylamine 在 三苯基膦 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以83%的产率得到o-[(N-4-dimethylaminobenzyl-N-methyl)aminomethyl]benzylamine
  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
• 作为产物：
  描述：

  4-(dimethylamino)-N-methylbenzylimine 在 sodium cyanoborohydride 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 10.0h， 生成 N-[{2-(azidomethyl)phenyl}methyl]-N-(4-dimethylaminobenzyl)methylamine
  参考文献：
  名称：

  A series of structurally simple chloroquine chemosensitizing dibemethin derivatives that inhibit chloroquine transport by PfCRT

  摘要：

  A series of 12 new dibemethin (N-benzyl-N-methyl-1-phenylmethanamine) derivatives bearing an Naminomethyl group attached to the one phenyl ring and an H, CI, OCH3 or N(CH3)(2) group on the other have been synthesized. These compounds all showed strong chloroquine chemosensitizing activity, comparable to verapamil, when present at 1 mu M in an in vitro culture of the chloroquine-resistant W2 strain of the human malaria parasite, Plasmodium falciparum. Their N-formylated derivatives also exhibited resistance-reversing activity, but only at substantially higher IC10 concentrations. A number of the dibemethin derivatives were shown to inhibit chloroquine transport via the parasite's 'chloroquine resistance transporter' (PfCRT) in a Xenopus laevis oocyte expression system. The reduced resistance-reversing activity of the formylated compounds relative to their free amine counterparts can probably be ascribed to two factors: decreased accumulation of the formylated dibemethins within the parasite's internal digestive vacuole (believed to be the site of action of chloroquine), and a reduced ability to inhibit PfCRT. The resistance-reversing activity of the compounds described here demonstrates that the amino group need not be attached to the two aromatic rings via a three or four carbon chain as has been suggested by previous QSAR studies. These compounds may be useful as potential side chains for attaching to a 4,7-dichloroquinoline group in order to generate new resistance-reversing chloroquine analogues with inherent antimalarial activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.026