N-(1.1-Dichlor-2-propinyl)-p-phenetidin | 14465-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(1.1-Dichlor-2-propinyl)-p-phenetidin
• 英文别名: 4-ethoxy-N-(2-methylbut-3-yn-2-yl)benzeneamine；4-ethoxy-N-(2-methylbut-3-yn-2-yl)aniline
• CAS: 14465-34-0
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: SDVYIAXXFRXKLF-UHFFFAOYSA-N

物化性质

• 沸点：
  140-146 °C(Press: 5 Torr)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1.1-Dichlor-2-propinyl)-p-phenetidin 在 copper(l) chloride 作用下， 生成 6-ethoxy-1,2-dihydro-2,2-dimethylquinoline
  参考文献：
  名称：

  New quinolinic derivatives as centrally active antioxidants

  摘要：

  A series of new 1,2-dihydro and 1,2,3,4-tetrahydroquinolines, synthesized from the corresponding propargylaniline intermediates, have been developed as antioxidants for the potential treatment of pathologies implicating central oxidative stress. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00122-0
• 作为产物：
  描述：

  3-氯-3-甲基-1-丁炔 、 对乙氧基苯胺 在 铜 、 三乙胺 、 copper(l) chloride 作用下， 生成 N-(1.1-Dichlor-2-propinyl)-p-phenetidin
  参考文献：
  名称：

  New quinolinic derivatives as centrally active antioxidants

  摘要：

  A series of new 1,2-dihydro and 1,2,3,4-tetrahydroquinolines, synthesized from the corresponding propargylaniline intermediates, have been developed as antioxidants for the potential treatment of pathologies implicating central oxidative stress. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00122-0

文献信息

• Antitrypanosomal Activity of 1,2-Dihydroquinolin-6-ols and Their Ester Derivatives
  作者：Jean Fotie、Marcel Kaiser、Dawn A. Delfín、Joshua Manley、Carolyn S. Reid、Jean-Marc Paris、Tanja Wenzler、Louis Maes、Kiran V. Mahasenan、Chenglong Li、Karl A. Werbovetz

  DOI：10.1021/jm900723w

  日期：2010.2.11

  The current chemotherapy for second stage human African trypanosomiasis is unsatisfactory. A synthetic optimization study based on the lead antitrypanosomal compound 1,2-dihydro-2,2,4-trimethylquinolin-6-yl 3,5-dimethoxybenzoate (TDR20364, 1a) was undertaken in an attempt to discover new trypanocides with potent in vivo activity. While 6-ether derivatives were less active than the lead compound, several N1-substituted derivatives displayed nanomolar IC50 values against T. b. rhodesiense STIB900 in vitro, with selectivity indexes up to > 18000. 1-Benzyl-1, 2-dlhydro-2,2,4-trimethylquinolin-6-yl acetate (10a) displayed an IC50 value of 0.014 mu M against these parasites and a selectivity index or 1700. Intraperitoneal administration of 10a at 50 (mg/kg)/day for 4 days caused a promising prolongation of lifespan in T. b. brucei STIB795-infected mice (> 14 days vs 7.75 days for untreated controls). Reactive oxygen species were produced when T. b. brucei were exposed to 10a in vitro, implicating oxidative stress in the trypanocidal mode of action of these 1,2-dihydroquinoline derivatives.