2-(pyridine-2-yl)-5,6-diamino-1H-benzimidazole | 1352399-49-5

• 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-(pyridine-2-yl)-5,6-diamino-1H-benzimidazole
• 英文别名: 2-(pyridin-2-yl)-5,6-diamino-1H-benzimidazole；2-pyridin-2-yl-1H-benzimidazole-5,6-diamine
• CAS: 1352399-49-5
• 化学式: C₁₂H₁₁N₅
• 分子量: 225.253
• InChiKey: HIBMYQSVMCFZIE-UHFFFAOYSA-N

物化性质

• 沸点：
  568.7±58.0 °C(predicted)
• 密度：
  1.424±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(pyridine-2-yl)-5,6-diamino-1H-benzimidazole 、 菲醌 以 甲醇 为溶剂， 反应 2.0h， 以82.1%的产率得到2-(pyridine-2-yl)-1H-imidazolo[4,5-i]dibenzo[2,3-a:2',3'-c]phenazine
  参考文献：
  名称：

  DNA-binding and photocleavage studies of ruthenium(II) complexes containing asymmetric intercalative ligand

  摘要：

  A novel asymmetric ligand 2-(pyridine-2-yl)-1-H-imidazo[4,5-i]dibenzo[2,3-a:2',3'-c]phenazine (pidbp) and its ruthenium complexes [Ru(L)(2)(pidbp)](2+). (L=bpy (2, 2'- bipyridine), phen (1, 10 - phenanthroline)), have been synthesized and characterized by elemental analysis, ES-MS, H-1 NMR. Various methods support the conclusion that both Ru(II) complexes can intercalate into DNA base pairs. Complex [Ru(bPY)(2)(Pidbp)](2+) 4 exhibits its DNA "molecular light switch" properties. Furthermore, the two complexes are efficient DNA-photocleavers under irradiation at 365 nm, and complex 5 exhibits a stronger DNA-photocleavage efficiency than complex 4. The mechanism of DNA cleavage is an oxidative process by generating singlet oxygen. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2011.11.014
• 作为产物：
  描述：

  N,N’-二(对甲苯磺酰基)-1,2-苯二胺 在 sodium dithionite 、 硫酸 、 水 、 硝酸 、 溶剂黄146 、 sodium hydroxide 作用下， 以 溶剂黄146 为溶剂， 反应 8.0h， 生成 2-(pyridine-2-yl)-5,6-diamino-1H-benzimidazole
  参考文献：
  名称：

  DNA-binding and photocleavage studies of ruthenium(II) complexes containing asymmetric intercalative ligand

  摘要：

  A novel asymmetric ligand 2-(pyridine-2-yl)-1-H-imidazo[4,5-i]dibenzo[2,3-a:2',3'-c]phenazine (pidbp) and its ruthenium complexes [Ru(L)(2)(pidbp)](2+). (L=bpy (2, 2'- bipyridine), phen (1, 10 - phenanthroline)), have been synthesized and characterized by elemental analysis, ES-MS, H-1 NMR. Various methods support the conclusion that both Ru(II) complexes can intercalate into DNA base pairs. Complex [Ru(bPY)(2)(Pidbp)](2+) 4 exhibits its DNA "molecular light switch" properties. Furthermore, the two complexes are efficient DNA-photocleavers under irradiation at 365 nm, and complex 5 exhibits a stronger DNA-photocleavage efficiency than complex 4. The mechanism of DNA cleavage is an oxidative process by generating singlet oxygen. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2011.11.014

文献信息

• Ruthenium (II) complexes containing a new asymmetric ligand: DNA interaction, photocleavage and topoisomerase I inhibition
  作者：Xue-Wen Liu、Song-Bai Zhang、Lin Li、Yuan-Dao Chen、Ji-Lin Lu

  DOI：10.1016/j.jorganchem.2013.01.007

  日期：2013.4

  5-g]acenaphtho[1′,2′:2,3]quinoxaline (piaq) and its ruthenium complexes with [Ru(L)2(piaq)]2+ (L = bpy (2,2′-bipyridine), phen (1,10-phenanthroline)), have been synthesized, and their DNA-binding, photocleavage and DNA topoisomerase I inhibition properties were measured. Results suggested that both Ru(II) complexes can intercalate into DNA base pairs. Furthermore, the two complexes are efficient DNA-photocleavers

  一种新的不对称配体2-（吡啶-2-基）-1- H-咪唑并[4,5- g ] ac [1'，2'：2,3]喹喔啉（piaq）及其钌与[Ru（ L）2（piaq）] 2+（L = bpy（2,2'-联吡啶），phen（1,10-菲咯啉）），已合成，其DNA结合，光裂解和DNA拓扑异构酶I抑制特性分别为测量。结果表明，两种Ru（II）配合物均可插入DNA碱基对。此外，这两种复合物是在365 nm辐射下有效的DNA光切割剂，以及单线态氧（1 O 2）是DNA光裂解中的活性物种。拓扑异构酶抑制和DNA链传代试验表明这两种复合物都是DNA拓扑异构酶I的有效抑制剂。
• DNA Interaction, Photocleavage and Topoisomerase I Inhibition by Ru(II) Complex with a New Ligand Possessing Phenazine Unit
  作者：Xue-Wen Liu、You-Ming Shen、Jun-Shi Shu、Yang Xiao、Song-Bai Zhang、Ji-Lin Lu

  DOI：10.1007/s10895-015-1644-8

  日期：2015.9

  A new ruthenium complex with a dppz-like ligand pyidppz, [Ru(bpy)2(pyidppz)]2+ (pyidppz = 2-(pyridine-2-yl)imidazo-[4,5-b]dipyrido-[3,2-a:2′,3′-c]phenazine) has been synthesized and characterized by ES-MS, elemental analysis, 1H NMR. Intercalative mode of the complex bound to calf thymus DNA has been supported by different spectroscopic methods and viscosity measurements. The introduction of phenazine unit may be one of the main reasons for the weak emission of Ru(II) complex in aqueous solution. Under irradiation, this complex can efficiently cleave DNA. And the photocleavage reaction of the complex is found to be inhibited in the presence of singlet oxygen scavenger. Topoisomerase inhibition and DNA strand passage assay demonstrated that [Ru(bpy)2(pyidppz)]2+ and its parent complex [Ru(bpy)2(pyip)]2+ (pyip = 2-(pyridine-2-yl)imidazo[4,5-f][1,10]phenanthroline) can act as efficient catalytic inhibitor of DNA topoisomerase I.

  通过 ES-MS、元素分析和 1H NMR，合成并表征了一种具有 dppz 类配体 pyidppz 的新钌配合物 [Ru(mby)2(pyidppz)]2+（pyidppz = 2-(吡啶-2-基)咪唑并[4,5-b]二吡啶并[3,2-a:2′,3′-c]吩嗪）。通过不同的光谱方法和粘度测量，证实了与小牛胸腺 DNA 结合的复合物的互锁模式。酚嗪单元的引入可能是 Ru(II) 复合物在水溶液中发射微弱的主要原因之一。在辐照下，该复合物能有效地裂解 DNA。在单线态氧清除剂的存在下，该配合物的光裂解反应受到抑制。拓扑异构酶抑制和 DNA 链通过试验证明，[Ru(bpy)2(pyidppz)]2+ 及其母体复合物 [Ru(bpy)2(pyip)]2+（pyip = 2-(吡啶-2-基)咪唑并[4,5-f][1,10]菲罗啉）可作为 DNA 拓扑异构酶 I 的高效催化抑制剂。
• Synthesis, DNA-binding, and photocleavage studies of ruthenium(II) complexes with an asymmetric ligand
  作者：Xue-Wen Liu、Lin Li、Ji-Lin Lu、Yuan-Dao Chen、Da-Shun Zhang

  DOI：10.1080/00958972.2011.639364

  日期：2011.12.20

  An asymmetric ligand (pdpiq = 2-(pyridine-2-yl)-6,7-diphenyl-l-H-imidazo[4,5-g]quinoxaline) and its ruthenium complexes with [Ru(L)(2)pdpiq](2+) (L = bpy (2,2'-bipyridine) or phen (1,10-phenanthroline)) have been synthesized and characterized by elemental analysis, ES-MS, and H-1 NMR. The DNA-binding behaviors of these complexes were studied by spectroscopic methods and viscosity measurements. The results indicate that the complexes can intercalate into DNA base pairs. When irradiated at 365 nm, the two complexes promote the cleavage of plasmid pBR322DNA. The mechanism of DNA cleavage is an oxidative process by generating singlet oxygen.