N-[4-[(6-chloro-2-methoxyacridin-9-yl)amino]butyl]-2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]acetamide | 1154499-76-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-[4-[(6-chloro-2-methoxyacridin-9-yl)amino]butyl]-2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]acetamide
• CAS: 1154499-76-9
• 化学式: C₃₅H₄₄ClN₃O₆
• 分子量: 638.204
• InChiKey: WVYZMAGTDCQDLV-RDDKVSGWSA-N

物化性质

• 沸点：
  805.4±65.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  artemisinin acid chloride 、 N¹-(6-chloro-2-methoxyacridin-9-yl)butane-1,4-diamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 N-[4-[(6-chloro-2-methoxyacridin-9-yl)amino]butyl]-2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]acetamide
  参考文献：
  名称：

  Antitumour and antimalarial activity of artemisinin–acridine hybrids

  摘要：

  Artemisinin-acridine hybrids were prepared and evaluated for their in vitro activity against tumour cell lines and a chloroquine sensitive strain of Plasmodium falciparum. They showed a 2-4-fold increase in activity against HL60, MDA-MB-231 and MCF-7 cells in comparison with dihydroartemisinin (DHA) and moderate antimalarial activity. Strong evidence that the compounds induce apoptosis in HL60 cells was obtained by flow cytometry, which indicated accumulation of cells in the G1 phase of the cell cycle. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.028

文献信息

• Antitumour and antimalarial activity of artemisinin–acridine hybrids
  作者：Michael Jones、Amy E. Mercer、Paul A. Stocks、Louise J.I. La Pensée、Rick Cosstick、B. Kevin Park、Miriam E. Kennedy、Ivo Piantanida、Stephen A. Ward、Jill Davies、Patrick G. Bray、Sarah L. Rawe、Jonathan Baird、Tafadzwa Charidza、Omar Janneh、Paul M. O’Neill

  DOI：10.1016/j.bmcl.2009.02.028

  日期：2009.4

  Artemisinin-acridine hybrids were prepared and evaluated for their in vitro activity against tumour cell lines and a chloroquine sensitive strain of Plasmodium falciparum. They showed a 2-4-fold increase in activity against HL60, MDA-MB-231 and MCF-7 cells in comparison with dihydroartemisinin (DHA) and moderate antimalarial activity. Strong evidence that the compounds induce apoptosis in HL60 cells was obtained by flow cytometry, which indicated accumulation of cells in the G1 phase of the cell cycle. (C) 2009 Elsevier Ltd. All rights reserved.