N1,N1'-(1,10-phenanthroline-4,7-diyl)bis(N4,N4-dimethylbutane-1,4-diamine) | 1204587-49-4

• 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: N1,N1'-(1,10-phenanthroline-4,7-diyl)bis(N4,N4-dimethylbutane-1,4-diamine)
• 英文别名: 4-N,7-N-bis[4-(dimethylamino)butyl]-1,10-phenanthroline-4,7-diamine
• CAS: 1204587-49-4
• 化学式: C₂₄H₃₆N₆
• 分子量: 408.59
• InChiKey: WGWAHKQNGMRSEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,7-二氯-1,10-菲咯啉 、 4-二甲基氨基丁胺 以 乙醇 为溶剂， 反应 16.0h， 以65%的产率得到N1,N1'-(1,10-phenanthroline-4,7-diyl)bis(N4,N4-dimethylbutane-1,4-diamine)
  参考文献：
  名称：

  Design, synthesis and evaluation of 4,7-diamino-1,10-phenanthroline G-quadruplex ligands

  摘要：

  A series of 4,7-diamino-1,10-phenanthroline derivatives carrying positively charged side chains has been synthesized, and their G-quadruplex interaction evaluated by circular dichroism (CD) and surface plasmon resonance (SPR). In absence of side chains, 4,7-diamino-1,10-phenanthroline exhibits a weak but significant G-quadruplex stabilizing effect, compared to no stabilization by 1,10-phenanthroline. We hypothesize that this effect is due to increased basicity of the phenanthroline nitrogens and protonation or ion chelation to form a central positive charge which stack on the G-tetrad above the central ionic column. Introduction of positively charged side chains results in compounds with appreciable G-quadruplex stabilizing properties and high aqueous solubility, with the longer side chains giving more potent compounds. Ligands carrying guanidine side chains in general show higher quadruplex stabilizing activity and distinctly slower kinetic properties than their amino and dimethylamino analogues, possibly due to specific hydrogen bond interactions with the G-quadruplex loops. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.055

文献信息

• Design, synthesis and evaluation of 4,7-diamino-1,10-phenanthroline G-quadruplex ligands
  作者：Mads Corvinius Nielsen、Jonas Borch、Trond Ulven

  DOI：10.1016/j.bmc.2009.09.055

  日期：2009.12.15

  A series of 4,7-diamino-1,10-phenanthroline derivatives carrying positively charged side chains has been synthesized, and their G-quadruplex interaction evaluated by circular dichroism (CD) and surface plasmon resonance (SPR). In absence of side chains, 4,7-diamino-1,10-phenanthroline exhibits a weak but significant G-quadruplex stabilizing effect, compared to no stabilization by 1,10-phenanthroline. We hypothesize that this effect is due to increased basicity of the phenanthroline nitrogens and protonation or ion chelation to form a central positive charge which stack on the G-tetrad above the central ionic column. Introduction of positively charged side chains results in compounds with appreciable G-quadruplex stabilizing properties and high aqueous solubility, with the longer side chains giving more potent compounds. Ligands carrying guanidine side chains in general show higher quadruplex stabilizing activity and distinctly slower kinetic properties than their amino and dimethylamino analogues, possibly due to specific hydrogen bond interactions with the G-quadruplex loops. (C) 2009 Elsevier Ltd. All rights reserved.