N'-(6-chloro-2-methoxyacridin-9-yl)-N-[[4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]phenyl]methyl]propane-1,3-diamine | 1150591-75-5

• 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'-(6-chloro-2-methoxyacridin-9-yl)-N-[[4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]phenyl]methyl]propane-1,3-diamine
• CAS: 1150591-75-5
• 化学式: C₄₀H₄₈ClN₃O₆
• 分子量: 702.291
• InChiKey: JSXNXWKTHQHHDO-PZKRZDQXSA-N

物化性质

• 沸点：
  802.7±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)：
  8.7
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  92.3
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-((((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)methyl)benzaldehyde 、 N¹-(6-chloro-2-methoxy-acridin-9-yl)-propane-1,3-diamine 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到N'-(6-chloro-2-methoxyacridin-9-yl)-N-[[4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]phenyl]methyl]propane-1,3-diamine
  参考文献：
  名称：

  Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates

  摘要：

  A novel series of semi-synthetic trioxaquines and synthetic trioxolaquines were prepared, in moderate to good yields. Antimalarial activity was evaluated against both the chloroquine-sensitive 3D7 and resistant K1 strain of Plasmodium falciparum and both series of compounds were shown to be active in the low nanomolar range. For comparison the corresponding 9-amino acridine analogues were also prepared and shown to have low nanomolar activity like their quinoline counterparts. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.013

文献信息

• Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates
  作者：Nuna C.P. Araújo、Victoria Barton、Michael Jones、Paul A. Stocks、Stephen A. Ward、Jill Davies、Patrick G. Bray、Alison E. Shone、Maria L.S. Cristiano、Paul M. O’Neill

  DOI：10.1016/j.bmcl.2009.02.013

  日期：2009.4

  A novel series of semi-synthetic trioxaquines and synthetic trioxolaquines were prepared, in moderate to good yields. Antimalarial activity was evaluated against both the chloroquine-sensitive 3D7 and resistant K1 strain of Plasmodium falciparum and both series of compounds were shown to be active in the low nanomolar range. For comparison the corresponding 9-amino acridine analogues were also prepared and shown to have low nanomolar activity like their quinoline counterparts. (C) 2009 Elsevier Ltd. All rights reserved.