1,10-phenanthroline-₂-carbohydrazonamide | 1025-07-6

• 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: 1,10-phenanthroline-₂-carbohydrazonamide
• 英文别名: 2-amino(hydrazino)methyl-1,10-phenanthroline；1,10-phenanthroline-2-carboxamide hydrazone；1,10-phenanthroline-2-carboxamidehydrazone；N'-amino-1,10-phenanthroline-2-carboximidamide
• CAS: 1025-07-6
• 化学式: C₁₃H₁₁N₅
• 分子量: 237.264
• InChiKey: PLTQNPCYDVLCRM-UHFFFAOYSA-N

物化性质

• 熔点：
  192-193 °C (decomp)
• 沸点：
  472.3±48.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 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：
  90.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-萘醌 、 1,10-phenanthroline-₂-carbohydrazonamide 以 乙醇 为溶剂， 反应 6.0h， 以78%的产率得到3-(1,10-phenanthrolin-2-yl)-as-triazino[5,6-f]naphthalene
  参考文献：
  名称：

  Synthesis, characterization, and DNA-binding studies of ruthenium complexes [Ru(tpy)(ptn)]2+ and Ru(dmtpy)(ptn)]2+

  摘要：

  Two ruthenium(II) polypyridyl complexes [Ru(tpy)(ptn)](2+) (1) and Ru(dmtpy)(ptn)](2+) (2) (ptn = 3-(1,10-phenanthrolin-2-yl)-as-triazino[5,6-f]naphthalene, tpy = 2,2':6',2 ''-terpyridine, dmtpy = 5,5'-dimethyl-2,2':6',2 ''-terpyridine) have been synthesized and characterized by elemental analysis, H-1 NMR, mass spectrometry and crystal structure analysis. Spectroscopic studies together with isothermal titration calorimetry (ITC) and viscosity measurements prove that two complexes bind to DNA in an intercalative mode. ITC experiments show that the binding mode for complex 2 is entropically driven, while an entropy-driven initial binding of complex 1 is followed by an entropically and enthalpically favorable process. This difference may be attributed to the ancillary ligand effects on the DNA binding of Ru(II) complexes. Circular dichroism titrations of calf thymus DNA (CT-DNA) with Ru(II) complexes show that complexes 1 and 2 induce B to Z conformational transition of calf thymus DNA at low ionic strength (0.05 M NaCl). The induced Z-DNA conformation can revert to B form when Ru(II) complexes are displaced by ethidium bromide or at high ionic strengths ([NaCl] = 0.4 M), but keeps intact with temperature ranged from 25 to 90 degrees C. The unique structure and characteristics of Ru(II) complexes designed in this investigation will be useful for the study of Z-DNA. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2012.03.008
• 作为产物：
  描述：

  1,10-菲咯啉-2-甲腈; 邻菲咯啉-2-甲腈 在 肼 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以86%的产率得到1,10-phenanthroline-₂-carbohydrazonamide
  参考文献：
  名称：

  含有新型不对称三齿配体的钌（II）配合物：合成，结构，电化学和光谱性质

  摘要：

  三个新颖的不对称三齿 配体， 3-（1,10-菲咯啉-2-基）-5,6-二苯基-作为-三嗪（dppt），3-（1,10-菲咯啉-2-基）-以-triazino [5,6- f ] ac烯（pta）和3-（1,10-菲咯啉-2-基）-作为-triazino已经制备了[5，6- f ]菲（ptp）。合成了它们的均相钌配合物[Ru（L）2 ] 2+（L = dppt，pta或ptp）和杂相钌配合物[Ru（tpy）（L）] 2+并对其进行了表征1 H NMR， 质谱仪， 电子吸收光谱 和 循环伏安法。杂配钌配合物的特征还在于X射线晶体学。配合物的电化学和光谱研究表明，由于结构差异，与[Ru（tpy）3 ] 2+相比，其性质发生了变化。

  DOI：

  10.1039/b009680f

文献信息

• Targeting telomeric G-quadruplexes with the ruthenium(ii) complexes [Ru(bpy)2(ptpn)]2+ and [Ru(phen)2(ptpn)]2+
  作者：Xiang Chen、Jing-Heng Wu、Ying-Wei Lai、Rong Zhao、Hui Chao、Liang-Nian Ji

  DOI：10.1039/c3dt32921f

  日期：——

  Two ruthenium(II) polypyridyl complexes, [Ru(bpy)2(ptpn)]2+ (1) (bpy = 2,2′-bipyridine, ptpn = 3-(1,10-phenanthroline-2-yl)-as-triazino[5,6-f]1,10-phenanthroline) and [Ru(phen)2(ptpn)]2+ (2) (phen = 1,10-phenanthroline), were synthesized and characterized. Crystal structure analysis shows that complex 1 has a large planar aromatic area and possesses the potential to fit the geometric structure of G-quadruplex. The interaction of the G-quadruplex DNA with Ru(II) complexes was explored by means of circular dichroism (CD), fluorescence resonance energy transfer (FRET) melting assay, competitive FRET assay and polymerase chain reaction (PCR) stop assay. The results indicated that complexes 1 and 2 both have the ability to promote the formation and stabilization of the human telomeric d[(TTAGGG)n] (HTG22) quadruplex and exhibit high G-quadruplex DNA selectivity over duplex DNA. The telomere repeat amplification protocol (TRAP) assay and long-term proliferation experiments further demonstrate that the Ru(II) complexes are potent telomerase inhibitors and HeLa cell proliferation inhibitors.

  两种多吡啶钌(II)配合物[Ru(bpy)2(ptpn)]2+ (1)（bpy = 2,2′-联吡啶，ptpn = 3-(1,10-菲罗啉-2-基)-异三嗪并[5、6-f]1,10-菲罗啉）和[Ru(phen)2(ptpn)]2+（2）（phen = 1,10-菲罗啉）的合成和表征。晶体结构分析表明，复合物 1 具有较大的平面芳香区，具有符合 G-四链的几何结构的潜力。通过圆二色性（CD）、荧光共振能量转移（FRET）熔化试验、竞争性 FRET 试验和聚合酶链式反应（PCR）停止试验，研究了 G 型四链 DNA 与 Ru(II) 复合物的相互作用。结果表明，复合物 1 和 2 都具有促进人类端粒 d[(TTAGGG)n] (HTG22) 四重链形成和稳定的能力，并且对双链 DNA 具有较高的 G- 四重链 DNA 选择性。端粒重复扩增协议（TRAP）测定和长期增殖实验进一步证明，Ru（II）复合物是强效的端粒酶抑制剂和 HeLa 细胞增殖抑制剂。
• Chiral Ru ^II ‐Pt ^II Complexes Inducing Telomere Dysfunction against Cisplatin‐Resistant Cancer Cells
  作者：Kai Xiong、Cheng Ouyang、Jiaqi Liu、Johannes Karges、Xinlin Lin、Xiang Chen、Yu Chen、Jian Wan、Liangnian Ji、Hui Chao

  DOI：10.1002/anie.202204866

  日期：2022.8.15

  Chiral RuII-PtII complexes were developed to act as G-quadruplex stabilizers in molecular crowding environments. When encapsulated with biotin-functionalized DNA cages, the nanoparticles induced telomere dysfunction and displayed significant antitumor activity against cisplatin-resistant cancer cells.

  开发了手性 Ru II -Pt II配合物作为分子拥挤环境中的 G-四链体稳定剂。当用生物素功能化的 DNA 笼包裹时，纳米颗粒会诱导端粒功能障碍，并对顺铂耐药的癌细胞表现出显着的抗肿瘤活性。
• Sugiyarto, Kristian H.; Craig, Donald C.; Rae, A. David, Australian Journal of Chemistry, 1996, vol. 49, # 4, p. 505 - 515
  作者：Sugiyarto, Kristian H.、Craig, Donald C.、Rae, A. David、Goodwin, Harold A.

  DOI：——

  日期：——
• The new and simple ‘LEGO’ system: Its application for the synthesis of 6-oligopyridyl-1,5,12-triazatriphenylenes
  作者：Gunther R. Pabst、Oliver C. Pfu¨ller、Ju¨rgen Sauer

  DOI：10.1016/s0040-4039(98)02044-9

  日期：1998.11

  The condensation of 1,10-phenanthroline-5,6-dione 1 with amidrazones 2 leads to 6-hetaryl-substituted 1,2,4,8,9-pentaazatriphenylenes 3. These condensed 1,2,4-triazines can be easily transformed to pyridines by [4+2] cycloaddition with norborna-2,5-diene followed by [4+2] cycloreversions of nitrogen and cyclopentadiene. This reaction sequence offers a new, simple and general access to 6-oligopyridyl-1,5, 1 2-triazatriphenylenes 4. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis, characterization, and DNA-binding studies of ruthenium complexes [Ru(tpy)(ptn)]2+ and Ru(dmtpy)(ptn)]2+
  作者：Lü-Ying Li、Hai-Na Jia、Hui-Juan Yu、Ke-Jie Du、Qi-Tian Lin、Kang-Qiang Qiu、Hui Chao、Liang-Nian Ji

  DOI：10.1016/j.jinorgbio.2012.03.008

  日期：2012.8

  Two ruthenium(II) polypyridyl complexes [Ru(tpy)(ptn)](2+) (1) and Ru(dmtpy)(ptn)](2+) (2) (ptn = 3-(1,10-phenanthrolin-2-yl)-as-triazino[5,6-f]naphthalene, tpy = 2,2':6',2 ''-terpyridine, dmtpy = 5,5'-dimethyl-2,2':6',2 ''-terpyridine) have been synthesized and characterized by elemental analysis, H-1 NMR, mass spectrometry and crystal structure analysis. Spectroscopic studies together with isothermal titration calorimetry (ITC) and viscosity measurements prove that two complexes bind to DNA in an intercalative mode. ITC experiments show that the binding mode for complex 2 is entropically driven, while an entropy-driven initial binding of complex 1 is followed by an entropically and enthalpically favorable process. This difference may be attributed to the ancillary ligand effects on the DNA binding of Ru(II) complexes. Circular dichroism titrations of calf thymus DNA (CT-DNA) with Ru(II) complexes show that complexes 1 and 2 induce B to Z conformational transition of calf thymus DNA at low ionic strength (0.05 M NaCl). The induced Z-DNA conformation can revert to B form when Ru(II) complexes are displaced by ethidium bromide or at high ionic strengths ([NaCl] = 0.4 M), but keeps intact with temperature ranged from 25 to 90 degrees C. The unique structure and characteristics of Ru(II) complexes designed in this investigation will be useful for the study of Z-DNA. (C) 2012 Elsevier Inc. All rights reserved.