2-(2-pyridyl)-1H-anthra[1,2-d]imidazole-6,11-dione | 942119-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(2-pyridyl)-1H-anthra[1,2-d]imidazole-6,11-dione
• 英文别名: 2-pyridyl-1H-anthra[1,2-d]imidazole-6,11-dione；PAIDH；2-pyridin-2-yl-3H-naphtho[3,2-e]benzimidazole-6,11-dione
• CAS: 942119-31-5
• 化学式: C₂₀H₁₁N₃O₂
• 分子量: 325.326
• InChiKey: RLDKVMCWOQMHIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-pyridyl)-1H-anthra[1,2-d]imidazole-6,11-dione 、 [(η⁶-p-cymene)Ru(Br)(μ-Br)]₂ 以 甲醇 为溶剂， 反应 12.0h， 以40%的产率得到[Ru^II(η⁶-p-cym)(2-pyridyl-1H-anthra[1,2-d]imidazole-6,11-dione)Br]Br
  参考文献：
  名称：

  细胞毒性的Ru II - p一个anthraimidazoledione的-cymene络合物：卤化物依赖解稳定性，反应性和耐失活缺氧†

  摘要：

  钌II - （η 6 - p -cymene）基于配体轴承式anthraimidazoldione的络合物（PAIDH）的[Ru II（η 6 - p -cymene）（PAIDH）（X）] +（其中，X = Cl，Br和I）对肝细胞癌（HepG2），人胰腺癌（MIA PaCa-2）和三重阴性人类转移性乳腺腺癌（MDA-MB-231）表现出优异的体外抗增殖活性（IC 50范围为1-2μM）。ESI-MS和1 H NMR数据表明，该络合物在pH 7.4（4 mM NaCl）的水溶液中稳定，在24小时内水解率不到10％。但是，当配位卤化物是溴（2）或碘（3），络合物将卤化物与溶液中的氯化物交换。交换取决于氯化物浓度。溴配合物2观察到最快的氯离子交换，碘配合物3观察到最慢，表明后者的动力学惰性较高。复合物3与谷胱甘肽（GSH）和9-乙基鸟嘌呤（9-EtG）的相互作用最弱。ESI-MS研究显示，即

  DOI：

  10.1039/c8dt04687e
• 作为产物：
  描述：

  吡啶-2-甲醛 、 1,2-二氨基蒽醌 在 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以75%的产率得到2-(2-pyridyl)-1H-anthra[1,2-d]imidazole-6,11-dione
  参考文献：
  名称：

  细胞毒性的Ru II - p一个anthraimidazoledione的-cymene络合物：卤化物依赖解稳定性，反应性和耐失活缺氧†

  摘要：

  钌II - （η 6 - p -cymene）基于配体轴承式anthraimidazoldione的络合物（PAIDH）的[Ru II（η 6 - p -cymene）（PAIDH）（X）] +（其中，X = Cl，Br和I）对肝细胞癌（HepG2），人胰腺癌（MIA PaCa-2）和三重阴性人类转移性乳腺腺癌（MDA-MB-231）表现出优异的体外抗增殖活性（IC 50范围为1-2μM）。ESI-MS和1 H NMR数据表明，该络合物在pH 7.4（4 mM NaCl）的水溶液中稳定，在24小时内水解率不到10％。但是，当配位卤化物是溴（2）或碘（3），络合物将卤化物与溶液中的氯化物交换。交换取决于氯化物浓度。溴配合物2观察到最快的氯离子交换，碘配合物3观察到最慢，表明后者的动力学惰性较高。复合物3与谷胱甘肽（GSH）和9-乙基鸟嘌呤（9-EtG）的相互作用最弱。ESI-MS研究显示，即

  DOI：

  10.1039/c8dt04687e

文献信息

• Hydrogen bond assisted photoinduced intramolecular electron transfer and proton coupled electron transfer in an ultrafast time domain using a ruthenium-anthraquinone dyad†
  作者：Ananta Dey、Jayanta Dana、Sunil Aute、Amitava Das、Hirendra N. Ghosh

  DOI：10.1039/c9pp00135b

  日期：2019.10

  anthraquinone moiety of complex 1 is fused to a benzi-imidazole system bearing COAQ⋯HNIm based H-bonding at one side of the anthraquinone moiety so that intramolecular hydrogen bonding from the imidazole group to the nearby quinone carbonyl can occur. The hydrogen bond formation involving the semiquinone radical anion produced through the photoinduced reduction process in Ru–im–AQ and the imidazole proton

  醌在光系统II的自然光合作用系统中作为主要电子受体发挥着重要作用，并且已知氢键供体或质子化促进了醌的还原。在这项研究中，已合成了通过刚性咪唑（Im）间隔基与蒽醌（AQ）官能团偶联的钌（II）聚吡啶基配合物1，以研究H键对热和光诱导电子转移反应的影响。配合物1的蒽醌部分与带有C O AQ ⋯HN Im的苯并咪唑系统融合在蒽醌部分的一侧上进行氢键结合，从而可以发生从咪唑基团到附近的醌羰基的分子内氢键。涉及通过光致还原方法中的Ru-IM-AQ中产生的半醌自由基阴离子和在复合物中的咪唑质子的氢键形成1导致的复杂的单电子还原电位的显著正移位1。通过使用飞秒瞬态吸收光谱研究了形成电荷分离态的动力学。在水和还原的蒽醌之间的氢键解释了这些电荷分离态的热力学和动力学稳定性。已经尝试评估驱动力和溶剂极性在配合物1中的光诱导电子转移速率中的相对重要性。蒽醌自由基阴离子（AQ的490nm处的瞬态吸收带- ），并在
• Cobalt complexes with redox-active anthraquinone-type ligands
  作者：Takuya Shiga、Rina Kumamaru、Graham N. Newton、Hiroki Oshio

  DOI：10.1039/c8dt00586a

  日期：——

  anthraquinone-type multidentate ligands, HL1–3 (HL = 2-R-1H-anthra[1,2-d]imidazole-6,11-dione; HL1: R = (2-pyridyl), HL2; R = (4,6-dimethyl-2-pyridyl), HL3; R = (6-methoxy-2-pyridyl)), were prepared, and their complexation behaviour was investigated. Three bis-chelate cobalt complexes with the formula [CoII(L1–3)2]·n(solv.) (1, 2, and 3 for HL1, HL2, and HL3, respectively), in which the ligands adopted tridentate

  三个蒽醌型多齿配体，HL 1-3（HL = 2-R-1 H-蒽[1,2- d ]咪唑-6,11-二酮； HL 1：R =（2-吡啶基），HL 2；制备R ＝（4，6-二甲基-2-吡啶基），HL 3； R ＝（6-甲氧基-2-吡啶基）），并研究它们的络合行为。三个双-螯合物钴配合物与式[CO II（L 1-3）2 ]· Ñ（溶剂）（1，2，和3为HL 1，HL 2，和HL 3，分别），其中配体采用三齿结合模式，合成和结构特征通过单晶X射线分析。在CH 2 Cl 2中对1-3的电化学研究揭示了三个可逆的氧化还原波，分别分配给配体和以钴为中心的过程。还获得了其中HL 1采用双齿结合模式，稳定单螯合物[Co II（HL 1）（NO 3）2（DMF）2 ]（4）物种和三螯合物[Co III（L 1）的复合物。）3 ]（5）络合物，其中钴离子处于3+状态。在DMF中研究了配合物5的电化学性质，发现与配合物1相比，Co（II）/
• Neutral and cationic cyclometallated Ir(III) complexes of anthra[1,2-d]imidazole-6,11-dione-derived ligands: Syntheses, structures and spectroscopic characterisation
  作者：Andrew J. Hallett、Benjamin D. Ward、Benson M. Kariuki、Simon J.A. Pope

  DOI：10.1016/j.jorganchem.2010.07.017

  日期：2010.10

  The syntheses of two new ligands and five new heteroleptic cyclometallated Ir(III) complexes are reported. The ligands are based upon a functionalised anthra[1,2-d]imidazole-6,11-dione core giving LH1 (3) incorporating a pendant pyridine, quinoline or thiophene unit respectively. Neutrally charged, octahedral complexes [Ir(ppy)(2)(L1-3)] are chelated by two cyclometallated phenylpyridine (ppy) ligands and a third, ancillary deprotonated ligand L1-3, whilst cationic analogues could only be isolated for [Ir(ppy)(2)(LH1-2)] [PF6]. X-ray crystal structures for [Ir(ppy)(2)(L-1)], [Ir(ppy)(2)(LH1)][PF6] and [Ir(ppy)(2)(L-2)] showed the complexes adopt a distorted octahedral coordination geometry, with the anthra[1,2-d]imidazole-6,11dione ligands coordinating in a bidentate fashion. Preliminary DFT calculations revealed that for the complexes of LH1 and LH2 the LUMO is exclusively localized on the ancillary ligand, whereas the nature of the HOMO depends on the protonation state of the ancillary ligand, often being composed of both Ir(III) and phenylpyridine character. UV-vis. and luminescence data showed that the ligands absorb into the visible region ca. 400 nm and emit ca. 560 nm, both of which are attributed to an intra-ligand CT transition within the anthra[1,2-d]imidazole-6,11-dione core. The complexes display absorption bands attributed to overlapping ligand-centred and (MLCT)-M-1-type electronic transitions, whilst only [Ir(ppy)(2)(L-2)] appeared to possess typical (MLCT)-M-3 behaviour (lambda(em) 616 nm; tau = 96 ns in aerated MeCN). The remaining complexes were generally visibly emissive (lambda(em) approximate to 560-570 nm; tau < 10 ns in aerated MeCN) with very oxygen-sensitive lifetimes more indicative of ligand-centred processes. (C) 2010 Elsevier B.V. All rights reserved.
• Synthesis, DNA Binding, and <i>Leishmania</i> Topoisomerase Inhibition Activities of a Novel Series of Anthra[1,2-<i>d</i>]imidazole-6,11-dione Derivatives
  作者：Padmaparna Chaudhuri、Hemanta K. Majumder、Santanu Bhattacharya

  DOI：10.1021/jm0610604

  日期：2007.5.1

  Nine novel anthra[1,2-d]imidazole-6,11-diones, differing in their side chain, were synthesized. UV-vis spectroscopy and viscometric titrations of these molecules with duplex DNA were used to assess their binding with DNA. Five of the nine compounds showed high inhibition activity against topoisomerase I of Leishmania donovani, with the one bearing the tetrazole side chain exhibiting an IC50 - 1 mu M. The inhibition activities were not related with their DNA binding affinity and depended on the nature of the side chain.
• Redox responsive luminescent switch based on a ruthenium(II) complex [Ru(bpy)2(PAIDH)]2+
  作者：Yi-Xian Yuan、Yu Chen、Yi-Can Wang、Cheng-Yong Su、Si-Min Liang、Hui Chao、Liang-Nian Ji

  DOI：10.1016/j.inoche.2008.05.026

  日期：2008.9

  A new ruthenium(II) polypyridine complex, [Ru(bpy)(2)(PAIDH)](2+) (1) (bpy = 2,2'-bipyridine; PAIDH = 2-pyridyl-1H-anthra[1,2-d]imidazole-6,11-dione) has been found to display electrochemically "off-on" luminescent switch through exchanging two protons and two electrons between the quinone/hydroquinone redox couple at room temperature. (C) 2008 Elsevier B.V. All rights reserved.