2-(1H-indol-3-yl)-1H-imidazo[4,5-f][1,10]phenanthroline | 852107-87-0

• 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: 2-(1H-indol-3-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: (indole)imidazo[4,5-f]1,10-phenanthroline；2-(Indole-3-yl)-imidazolo[4,5-f][1,10]phenanthroline
• CAS: 852107-87-0
• 化学式: C₂₁H₁₃N₅
• 分子量: 335.368
• InChiKey: WAPLJTPWONPSSY-UHFFFAOYSA-N

物化性质

• 沸点：
  720.2±70.0 °C(Predicted)
• 密度：
  1.474±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-indol-3-yl)-1H-imidazo[4,5-f][1,10]phenanthroline 、 五羰基氯铼(I) 以 乙醇 为溶剂， 以81%的产率得到Re(CO)3Cl(2-(3-indolyl)-imidazo[4,5-f]-[1,10]phenanthroline)
  参考文献：
  名称：

  A rhenium(I) complex with indolyl-containing ligand: Synthesis, photophysical properties and theoretical studies

  摘要：

  A rhenium(I) tricarbonyl complex, [Re(CO)(3)(IDIMPhen)Cl] (IDIMPhen-Re) [where IDIMPhen = 2-(3-indolyl)-imidazo[4,5-f]-[1,10] phenanthroline], have been successfully synthesized and fully characterized by H-1 NMR, C-13 NMR, IR, GC-MS, elemental analysis, UV-Vis and cyclic voltammetry (CV). Meanwhile, the electronic structure and spectroscopic features of IDIMPhen-Re have been investigated using the density functional theory (DFT) and time-dependent DFT methods. Based on the calculated results, the experiment data are explained in great detail. The calculated orbital energies of the HOMO and LUMO of IDIMPhen-Re are in reasonable agreement with those obtained from the electrochemical measurements. The lowest lying singlet -> singlet absorption band of IDIMPhen-Re, corresponding to the prominent absorption peak at 447 nm observed in experiments, should be assigned to the pure HOMO -> LUMO transition. The calculated IP and EA show that IDIMPhen-Re possesses the good hole-transfer ability and the balanced transport of electrons and holes is more accessible compared with its analogue Phen-Re. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.01.001
• 作为产物：
  描述：

  3-吲哚甲醛 、 1,10-邻二氮杂菲-5,6-二酮 在 ammonium acetate 、 溶剂黄146 作用下， 以80%的产率得到2-(1H-indol-3-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  四种咪唑并[4,5-f]1,10-菲咯啉衍生物的合成、表征和DNA结合

  摘要：

  四种咪唑并[4,5- f ]1,10-菲咯啉类化合物2,6-(二甲氧基吡啶基)咪唑并[4,5- f ]1,10-菲咯啉一水合物(C 20 H 17 N 5 O 3 ) 1a , (indole)imidazo[4,5 - f ]1,10-phenanthroline 乙醇一水合物 (C 23 H 21 N 5 O 2 ) 2a , (benzo[b]噻吩)imidazo[4,5 - f ]1,10-菲咯啉 (C 21 H 12 N 4 S) 3和(4,5-二甲基噻吩)咪唑并[4,5 - f ]1,10-菲咯啉(C 19 H 14 N 4 S) 4被报道。这些化合物在二甲基亚砜-d 6 (DMSO- d 6 ) 溶液中通过1 H 和13 C NMR 光谱进行表征，并通过13 C NMR 光谱使用交叉极化魔角旋转 (CP/MAS) 技术在固态中表征. 1 H和13的下为液体状态的NMR谱1和2

  DOI：

  10.1016/j.molstruc.2021.131235

文献信息

• 2-Indolyl Imidazo [4,5-d] Phenanthroline Derivatives and Their Use in the Treatment for Cancer
  申请人：Huesca Mario

  公开号：US20100168417A1

  公开（公告）日：2010-07-01

  2-indolyl imidazo[4,5-d]phenanthroline compounds of Formula I that are capable of intracellular chelation of transition metals and of exerting antiproliferative effects in cancer cells, that are cytostatic and/or cytotoxic, are provided. Compounds of Formula I can also induce apoptosis in cancer cells and are thus capable of exerting a cytotoxic effect on cancer cells. The compounds of Formula I are also capable of selectively inhibiting the proliferation of one or more of prostate cancer cells, colon cancer cells, non-small lung cancer cells and leukemia cells. The compounds of Formula I are also capable of increasing the expression of the zinc-regulated tumour suppressor, KLF4 and thus are useful in inhibiting the proliferation of cancer cells in which KLF4 functions as a tumour-suppressor, including, but not limited to, bladder cancer, cancers of the gastrointestinal tract and various leukemias.

  提供了能够在细胞内与过渡金属螯合并对癌细胞产生抗增殖作用的Formula I的2-吲哚基咪唑并[4,5-d]菲啰啉化合物，这些化合物具有细胞静止和/或细胞毒作用。Formula I的化合物还可以诱导癌细胞凋亡，因此能够对癌细胞产生细胞毒作用。Formula I的化合物还能够选择性地抑制前列腺癌细胞、结肠癌细胞、非小细胞肺癌细胞和白血病细胞中的一个或多个的增殖。Formula I的化合物还能够增加锌调节的肿瘤抑制基因KLF4的表达，因此在抑制KLF4作为肿瘤抑制基因发挥作用的癌细胞的增殖方面具有用处，包括但不限于膀胱癌、胃肠道癌和各种白血病。
• Hypoxia efficient and glutathione-resistant cytoselective ruthenium(<scp>ii</scp>)-<i>p</i>-cymene-arylimidazophenanthroline complexes: biomolecular interaction and live cell imaging
  作者：Ashaparna Mondal、Priyankar Paira

  DOI：10.1039/d0dt02069a

  日期：——

  the 2-aryl substituted imidazophenanthroline ligands make the Ru(II) complex a decent DNA intercalator by affording planarity. Among the four Ru(II) complexes (RuL1–RuL4), [(η6-p-cymene)RuIIClK2-N,N-(2-(naphthalene-1-yl)-1H-imidazo[4,5-f][1,10]phenanthroline)}]PF6 (RuL4) exhibited the best cytoselectivity in two cancer cell lines (Caco-2 and HeLa), and [(η6-p-Cymene)RuIIClK2-N,N-(2-(anthracen-9-yl)-1H-imidazo[4

  由于市售抗癌药的副作用，我们设计了一系列基于钌的荧光抗癌药，已证明它们具有靶向特异性，高度细胞选择性，亲脂性，水溶性，低氧效率和谷胱甘肽抗性。在这里，我们开发了新型的钌（II）-对-cymene-2-芳基-咪唑并菲咯啉骨架作为有效的DNA靶向剂。具体地，通过提供平面性，2-芳基取代的咪唑并菲咯啉配体使Ru（II）络合物成为体面的DNA嵌入剂。在四个的Ru（II）络合物（RuL1-RuL4），[（η 6 - p -cymene）钌II氯[KP 2 - Ñ，N-（2-（萘-1-基）-1 H-咪唑并[4,5- f ] [1,10]菲咯啉）}] PF 6（RuL4）在两种癌细胞系中均表现出最佳的细胞选择性（Caco -2和HeLa）和[（η 6 - p -Cymene）钌II氯[KP 2 - ñ，ñ - （2-（蒽-9-基）-1- ħ -咪唑并[4,5- ˚F ] [ 1,10]菲咯啉}} PF
• Mitochondria-targeted half-sandwich iridium(<scp>iii</scp>)-Cp*-arylimidazophenanthroline complexes as antiproliferative and bioimaging agents against triple negative breast cancer cells MDA-MB-468
  作者：Ashaparna Mondal、Shanooja Shanavas、Utsav Sen、Utpal Das、Nilmadhab Roy、Bipasha Bose、Priyankar Paira

  DOI：10.1039/d2ra01036d

  日期：——

  The subcellular localization study of the complex revealed the localization of the compound in cytoplasm thereby pointing to a possible mitochondrial localization and consequent mitochondrial dysfunction via MMP alteration and ROS generation. Moreover, the IrL1 complex facilitated a substantial G1 phase cell-cycle arrest of MDA-MB-468 cells at the highest tested concentration of 5 μM. The study verdicts

  为了减少已上市抗癌药物对三阴性乳腺癌细胞的副作用，我们报道了线粒体靶向半夹心铱 ( III )-Cp*-芳基咪唑并菲咯啉复合物用于 MDA-MB-468 细胞治疗和诊断。在五种 Ir( III ) 配合物 ( IrL1–IrL5 ) 中，[铱( III )-Cp*-2-(naphthalen-1-yl)-1 H-咪唑并[4,5- f ][1,10]菲咯啉]PF 6 ( IrL1) 与正常 HaCaT 细胞相比，对 MDA-MB-468 细胞表现出最佳的细胞选择性，以及与 DNA 和血清白蛋白的出色结合功效。该复合物的亚细胞定位研究揭示了该化合物在细胞质中的定位，从而表明可能存在线粒体定位，并通过MMP 改变和 ROS 产生导致线粒体功能障碍。此外，IrL1复合物在 5 μM 的最高测试浓度下促进了 MDA-MB-468 细胞的实质性 G 1期细胞周期停滞。研究结论支持IrL1的前瞻性治疗潜
• Rhenium(I) Tricarbonyl Complexes of 1,10-Phenanthroline Derivatives with Unexpectedly High Cytotoxicity
  作者：Lucy E. Enslin、Kallol Purkait、Maria Dalla Pozza、Bruno Saubamea、Pierre Mesdom、Hendrik G. Visser、Gilles Gasser、Marietjie Schutte-Smith

  DOI：10.1021/acs.inorgchem.3c00730

  日期：2023.8.7

  pathway. Complex 3 induced a paraptosis pathway for cell killing while 6 did not induce any of our other tested pathways, namely, necrosis, paraptosis, and autophagy. Both complexes 3 and 6 were found to be involved in mitochondrial dysfunction and downregulated the ATP production of PC3 cells. To the best of our knowledge, this report presents some of the most cytotoxic Re(I) carbonyl complexes with exceptionally

  八种铼(I)三羰基水配合物，通式为fac -[Re(CO) 3 ( N,N ′-bid)(H 2 O)][NO 3 ] ( 1–8 )，其中N,N ′- bid是(2,6-二甲氧基吡啶基)咪唑并[4,5- f ]1,10-菲咯啉( L1 )、(吲哚)咪唑并[4,5- f ]1,10-菲咯啉( L2 )、(5-甲氧基吲哚) )-咪唑并[4,5- f ]1,10-菲咯啉 ( L3 )、(联苯)咪唑并[4,5- f ]1,10-菲咯啉 ( L4 )、(芴)咪唑并[4,5- f ] 1,10-菲咯啉 ( L5 )、(苯并[ b ]噻吩)咪唑并[4,5- f ]1,10-菲咯啉 ( L6 )、(5-溴噻唑)咪唑[4,5- f ]1,10-合成菲咯啉 ( L7 ) 和 (4,5-二甲基噻吩)咪唑并[4,5- f ]1,10-菲咯啉 ( L8 )，并使用1 H 和13 C 1 H} NMR、FT-IR
• Cellular uptake, cytotoxicity, apoptosis and DNA-binding investigations of Ru(II) complexes
  作者：C. Shobha Devi、Penumaka Nagababu、Sumathi Natarajan、N. Deepika、P. Venkat Reddy、N. Veerababu、Surya S. Singh、S. Satyanarayana

  DOI：10.1016/j.ejmech.2013.11.005

  日期：2014.1

  Three new compounds, [Ru(Hdpa)(2)PyIP](ClO4)(2)center dot 2H(2)O (1) [Ru(Hdpa)(2)FyIP](ClO4)(2)center dot 2H(2)O (2) and [Ru(Hdpa)(2)IIP](ClO4)(2)center dot 2H(2)O (3) have been synthesized and characterized by spectroscopic techniques such as elemental analysis, UV/Vis, FT-IR, H-1 NMR, C-13 NMR and mass spectra. The CT-DNA binding properties of 1-3 have been investigated by absorption, emission spectroscopy and viscosity measurements. Experimental results suggested that they can interact with DNA through intercalative mode with different binding strengths. These were found to promote the cleavage of plasmid DNA. Cell viability results indicated that all compounds showed significant dose dependent cytotoxicity in selected cell lines and 1 shown higher cytotoxicity than dsplatin on HeLa cells. Cellular uptake studies were studied by flow cytometry and confocal microscopy. (C) 2013 Elsevier Masson SAS. All rights reserved.