2-(6-nitrobenzo[d][1,3]dioxol-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline | 851427-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(6-nitrobenzo[d][1,3]dioxol-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2'-(2''-nitro-3'',4''-methylenedioxyphenyl)imidazo-[4',5'-f][1,10]-phenanthroline；NMIP；2-(6-nitro-1,3-benzodioxol-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• CAS: 851427-54-8
• 化学式: C₂₀H₁₁N₅O₄
• 分子量: 385.338
• InChiKey: ZMUONLCMSWKYAU-UHFFFAOYSA-N

物化性质

• 沸点：
  721.5±70.0 °C(Predicted)
• 密度：
  1.618±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 、 ammonium hexafluorophosphate 、 2-(6-nitrobenzo[d][1,3]dioxol-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline 以 甲醇 、 二氯甲烷 为溶剂， 以84 %的产率得到[Ir(ppy)₂(2-(6-nitrobenzo[d][1,3]dioxol-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline)](PF₆)
  参考文献：
  名称：

  White light increases anticancer effectiveness of iridium(III) complexes toward lung cancer A549 cells

  摘要：

  DOI：

  10.1016/j.jinorgbio.2024.112652
• 作为产物：
  描述：

  6-硝基胡椒醛 、 1,10-邻二氮杂菲-5,6-二酮 在 ammonium acetate 、 溶剂黄146 作用下， 生成 2-(6-nitrobenzo[d][1,3]dioxol-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  White light increases anticancer effectiveness of iridium(III) complexes toward lung cancer A549 cells

  摘要：

  DOI：

  10.1016/j.jinorgbio.2024.112652

文献信息

• DNA-binding and photocleavage studies of [Ru(phen)2(NMIP)]2+
  作者：Li-Feng Tan、Hui Chao、Yun-Jun Liu、Hong Li、Bin Sun、Liang-Nian Ji

  DOI：10.1016/j.ica.2004.10.030

  日期：2005.4

  A novel ligand 2'-(2"-nitro-3",4"-methylenedioxyphenyl)imidazo[4',5'-f][1,10]-phenanthroline (NMIP) and its complex [Ru(phen)(2)(NMIP)](2+) have been synthesized and characterized by mass spectroscopy, H-1 NMR and cyclic voltammetry. Binding of the complex with calf thymus DNA (CT DNA) has been investigated by spectroscopic methods, viscosity and electrophoresis measurements. The experimental results indicate that [Ru(phen)(2)(NMIP)](2+) binds to DNA via partial intercalative mode and the individual enantiomers of it bind to DNA in different rates. [Ru(phen)(2)(NMIP)](2+) has also been found to promote cleavage of plasmid pBR 322 DNA from the supercoiled Form I to the open circular Form 11 upon irradiation. (c) 2004 Published by Elsevier B.V.
• DNA-binding and photocleavage studies of mixed polypyridyl ruthenium(II) complexes with calf thymus DNA
  作者：Li-Feng Tan、Hui Chao

  DOI：10.1016/j.ica.2006.10.016

  日期：2007.4

  New mixed polypyridyl NMIP=2'-(2"-nitro-3",4"-methylenedioxyphenyl)imidazo-[4',5'-f][1,10]-phenanthroline, dmb=4,4'-dimethyl-2,2'-bipyridine, bpy = 2,2'-bipyridine} ruthenium(II) complexes [Ru(dmb)(2)(NMIP)](2+) (1) and [R-a(bpy)(2)(NMIP)](2+) (2) have been synthesized and characterized. The binding of these complexes to calf thymus DNA (CT-DNA) has been investigated with spectroscopic methods, viscosity and electrophoresis measurements. The experimental results indicate that both complexes could bind to DNA via partial intercalation from the minor/major groove. In addition, both complexes have been found to promote the single-stranded cleavage of plasmid pBR 322 DNA upon irradiation. Under comparable experimental conditions compared with [Ru(phen)(2)(NMIP)](2+), during the course of the dialysis at intervals of time, the CD signals of both complexes started from none, increased to the maximum magnitude, then no longer changed, and the activity of effective DNA cleavage dependence upon concentration degree lies in the following order: [Ru(phen)(2)NMIP](2+) > complex 2 > complex 1. (c) 2006 Elsevier B.V. All rights reserved.