N-methyl-N-(1,10-phenanthrolin-2-yl)-1,10-phenanthrolin-2-amine | 1240422-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: N-methyl-N-(1,10-phenanthrolin-2-yl)-1,10-phenanthrolin-2-amine
• CAS: 1240422-77-8
• 化学式: C₂₅H₁₇N₅
• 分子量: 387.443
• InChiKey: JCYJKGLGIQSPFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trans-dichlorobis(dimethyl sulfoxide)platinum(II) 、 N-methyl-N-(1,10-phenanthrolin-2-yl)-1,10-phenanthrolin-2-amine 以 甲醇 、 水 为溶剂， 反应 5.0h， 以78%的产率得到
  参考文献：
  名称：

  Aza-bridged bisphenanthrolinyl Pt(II) complexes: Efficient stabilization and topological selectivity on telomeric G-quadruplexes

  摘要：

  Two platinum complexes with an aza-bridged bis(1,10-phenanthrolin-2-yl)amine (bpa) were synthesized. The two phenanthrolines in bpa entered a flat plane prior to binding of nucleic acids, which bestowed on the two Pt complexes a significantly high stabilizing ability on both DNA and RNA G-quadruplexes. Further extending alkyl tail from aromatic coordination core enabled the complexes to distinguish GQ sequence based upon the topological folding structures and enhanced the selectivity of the complex against duplex DNA. This study paved the way to develop Pt complexes as GQ stabilizers for specific folding topology and the applications to disease and/or personalized anticancer medicine/therapy. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2016.11.011
• 作为产物：
  描述：

  N,N-bis-(1,10-phenanthrolin-2-yl)amine 、 碘甲烷 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 48.5h， 以53%的产率得到N-methyl-N-(1,10-phenanthrolin-2-yl)-1,10-phenanthrolin-2-amine
  参考文献：
  名称：

  氮杂桥联的bis-1,10-菲咯啉无环衍生物：合成，结构和区域选择性烷基化

  摘要：

  已经以方便的方式合成了一系列无环氮杂桥联的双-1，10-菲咯啉化合物。对所得化合物2和2· HCl进行了充分表征，并研究了它们的固态结构和NMR光谱性质，以评估结构单元如何影响烷基化反应。结果揭示了2的transoid结构。显示出2中的NMR峰变宽是由于不寻常的分子内CH hydrogenN氢键所致。这种独特的构象为制备氨基取代的双2,2'-1,10-菲咯啉衍生物和1,10-菲咯啉-N-烷基化的化合物提供了一种有效的区域选择性方法。

  DOI：

  10.1016/j.tetlet.2010.05.039

文献信息

• Aza-bridged bis-1,10-phenanthroline acyclic derivatives: synthesis, structure, and regioselective alkylation
  作者：Hsien-Chang Kao、Chia-Jung Hsu、Che-Wei Hsu、Chien-Ho Lin、Wen-Jwu Wang

  DOI：10.1016/j.tetlet.2010.05.039

  日期：2010.7

  to assess how the structural units affect the alkylation reactions. The results reveal the transoid structure for 2. The broadening NMR peak in 2 is shown to be due to an unusual intramolecular CH⋯N hydrogen bond. This unique conformation offers an efficient and regioselective method to prepare the amino-substituted bis-2,2′-1,10-phenanthroline derivatives and 1,10-phenanthrolino-N-alkylated compounds

  已经以方便的方式合成了一系列无环氮杂桥联的双-1，10-菲咯啉化合物。对所得化合物2和2· HCl进行了充分表征，并研究了它们的固态结构和NMR光谱性质，以评估结构单元如何影响烷基化反应。结果揭示了2的transoid结构。显示出2中的NMR峰变宽是由于不寻常的分子内CH hydrogenN氢键所致。这种独特的构象为制备氨基取代的双2,2'-1,10-菲咯啉衍生物和1,10-菲咯啉-N-烷基化的化合物提供了一种有效的区域选择性方法。
• Aza-bridged bisphenanthrolinyl Pt(II) complexes: Efficient stabilization and topological selectivity on telomeric G-quadruplexes
  作者：Lei He、Zhenyu Meng、Yi-qun Xie、Xiang Chen、Tianhu Li、Fangwei Shao

  DOI：10.1016/j.jinorgbio.2016.11.011

  日期：2017.1

  Two platinum complexes with an aza-bridged bis(1,10-phenanthrolin-2-yl)amine (bpa) were synthesized. The two phenanthrolines in bpa entered a flat plane prior to binding of nucleic acids, which bestowed on the two Pt complexes a significantly high stabilizing ability on both DNA and RNA G-quadruplexes. Further extending alkyl tail from aromatic coordination core enabled the complexes to distinguish GQ sequence based upon the topological folding structures and enhanced the selectivity of the complex against duplex DNA. This study paved the way to develop Pt complexes as GQ stabilizers for specific folding topology and the applications to disease and/or personalized anticancer medicine/therapy. (C) 2016 Elsevier Inc. All rights reserved.