N-[3-(N',N'-dimethylamino)-2,2-dimethylpropyl]-6-nitro-benzo[de]isoquinoline-1,3-dione | 1228441-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[3-(N',N'-dimethylamino)-2,2-dimethylpropyl]-6-nitro-benzo[de]isoquinoline-1,3-dione
• CAS: 1228441-31-3
• 化学式: C₁₉H₂₁N₃O₄
• 分子量: 355.393
• InChiKey: BOFNMJHUSDZSOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  83.76
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,6-二溴己烷 、 N-[3-(N',N'-dimethylamino)-2,2-dimethylpropyl]-6-nitro-benzo[de]isoquinoline-1,3-dione 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 504.0h， 以34.8%的产率得到2-{3-[1-(6-{1,1-dimethyl-1-[3-(1,3-dioxo-6-nitro-1,3-dihydro-benzo[de]isoquinolin-2-yl)-2,2-dimethylpropyl]ammonium}hexyl)-1,1dimethyl-ammonium]-2,2-dimethylpropyl}-6-nitro-benzo[de]isoquinoline-1,3-dione dibromide
  参考文献：
  名称：

  The bisnaphthalimides as new active lead compounds against Plasmodium falciparum

  摘要：

  The bisquaternary bisnaphthalimides are a versatile class of compounds being active against the malaria parasite Plasmodium falciparum in the lower nanomolar range of concentration combined with no cytotoxicity. The series of compounds is designed as choline analogues and interfering agents of the phosphatidylcholine biosynthesis. The qualitative analysis of the structure-activity relationships (SAR) revealed the importance of a long methylene middle chain of at least 8 methylene groups between the two bisquaternary naphthalimides or a monoquaternary naphthalimide consisting of a long alkyl chain attached to the positively charged nitrogen atom. Since the SARs are different from reported biscationic antimalarial drugs the mode of action remains to be elucidated. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.067
• 作为产物：
  描述：

  N,N,2,2-四甲基-1,3-丙二胺 、 4-硝基-1,8-萘醛酸酐 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以91%的产率得到N-[3-(N',N'-dimethylamino)-2,2-dimethylpropyl]-6-nitro-benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  The bisnaphthalimides as new active lead compounds against Plasmodium falciparum

  摘要：

  The bisquaternary bisnaphthalimides are a versatile class of compounds being active against the malaria parasite Plasmodium falciparum in the lower nanomolar range of concentration combined with no cytotoxicity. The series of compounds is designed as choline analogues and interfering agents of the phosphatidylcholine biosynthesis. The qualitative analysis of the structure-activity relationships (SAR) revealed the importance of a long methylene middle chain of at least 8 methylene groups between the two bisquaternary naphthalimides or a monoquaternary naphthalimide consisting of a long alkyl chain attached to the positively charged nitrogen atom. Since the SARs are different from reported biscationic antimalarial drugs the mode of action remains to be elucidated. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.067