1,10-phenanthroline-2,9-dicarbohydrazide | 137372-06-6

• 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-2,9-dicarbohydrazide
• CAS: 137372-06-6
• 化学式: C₁₄H₁₂N₆O₂
• 分子量: 296.288
• InChiKey: FAZMLXUMUWCOCL-UHFFFAOYSA-N

物化性质

• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,10-phenanthroline-2,9-dicarbohydrazide 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 N'²,N'⁹-bis[(1-ethylquinolinium-6-yl)methylene]-1,10-phenanthroline-2,9-dicarbohydrazide iodide
  参考文献：
  名称：

  Novel cationic bis(acylhydrazones) as modulators of Epstein–Barr virus immune evasion acting through disruption of interaction between nucleolin and G-quadruplexes of EBNA1 mRNA

  摘要：

  The oncogenic Epstein-Barr virus (EBV) evades the immune system through limiting the expression of its highly antigenic and essential genome maintenance protein, EBNA1, to the minimal level to ensure viral genome replication, thereby also minimizing the production of EBNA1-derived antigenic peptides. This regulation is based on inhibition of translation of the virally-encoded EBNA1 mRNA, and involves the interaction of host protein nucleolin (NCL) with G-quadruplex (G4) structures that form in the glycine-alanine repeat (GAr)-encoding sequence of the EBNA1 mRNA. Ligands that bind to these G4-RNA can prevent their interaction with NCL, leading to disinhibition of EBNA1 expression and antigen presentation, thereby interfering with the immune evasion of EBNA1 and therefore of EBV (M.J. Lista et al., Nature Commun., 2017, 8, 16043). In this work, we synthesized and studied a series of 20 cationic bis(acylhydrazone) derivatives designed as G4 ligands. The in vitro evaluation showed that most derivatives based on central pyridine (Py), naphthyridine (Naph) or phenanthroline (Phen) units were efficient G4 binders, in contrast to their pyrimidine (Pym) counterparts, which were poor G4 binders due to a significantly different molecular geometry. The influence of lateral heterocyclic units (N-substituted pyridinium or quinolinium residues) on G4-binding properties was also investigated. Two novel compounds, namely PyDH2 and PhenDH2, used at a 5 μM concentration, were able to significantly enhance EBNA1 expression in H1299 cells in a GAr-dependent manner, while being significantly less toxic than the prototype drug PhenDC3 (GI₅₀ > 50 μM). Antigen presentation, RNA pull-down and proximity ligation assays confirmed that the effect of both drugs was related to the disruption of NCL-EBNA1 mRNA interaction and the subsequent promotion of GAr-restricted antigen presentation. Our work provides a novel modular scaffold for the development of G-quadruplex-targeting drugs acting through interference with G4-protein interaction.

  DOI：

  10.1016/j.ejmech.2019.05.042
• 作为产物：
  描述：

  1,10-菲啰啉-2,9-二甲醛 在 硫酸 、 硝酸 、 一水合肼 作用下， 以 甲醇 为溶剂， 生成 1,10-phenanthroline-2,9-dicarbohydrazide
  参考文献：
  名称：

  基于 2,9-取代-1,10-菲咯啉衍生物的高选择性和强效抗癌剂

  摘要：

  摘要 一项关于在 2,9 位结构调整的 1,10-菲咯啉具有不同官能团如 –CH3 (S1)、>CO (S2)、–COOH (S3)、–COOCH3 ( S4) 和 –CONHNH2 (S5) 进行了描述。溶解度数据显示所有配体完全溶于二甲基亚砜（DMSO），中等溶于水。这些配体的光物理性质表明，共同的吸收峰出现在 270-300 nm 区域，发射光谱出现在 330-510 nm 区域，斯托克斯位移大为 85 nm。发现配体 (S1-S5) 与小牛胸腺脱氧核糖核酸 (CT-DNA) 和牛血清白蛋白 (BSA) 的结合常数分别为 105 M-1 和 104 M-1。从结合亲和力值 KSV (104 M-1) 和 Kapp (106 M-1) 证实了加入配体后 DNA 中溴化乙锭 (EtBr) 的荧光猝灭。配体与 DNA 的相互作用模式是通过嵌入或凹槽结合，这得到了粘度和计算机内研究的进一步支持。凝胶电泳研究表明，S4

  DOI：

  10.1016/j.inoche.2020.108085

文献信息

• NOVEL HYDRAZONE DERIVATIVES FOR PREVENTING OR TREATING EBV-RELATED CANCERS
  申请人：Université de Bretagne Occidentale

  公开号：EP3549938A1

  公开（公告）日：2019-10-09

  The present invention relates to novel bis-hydrazone derivatives of formula (I): wherein Ar1 and Ar2 may be identical or different and are each independently selected from the group consisting of groups of formula (II) and (III): Y1 and Z1 are independently CH or NRc+, provided that al least one of Y1 and Z1 is NRc+ and at least one of Y1 and Z1 is CH, and Ra, Rb, Rc, X2- and L as defined in the claims, or a hydrate or a solvate thereof. Compositions and kits comprising same are also described. Said bis-hydrazone derivatives of formula (I), compositions and kits are useful as drugs, in particular for treating or preventing cancers associated with the Epstein-Barr Virus.

  本发明涉及一种新的双酰肼衍生物，其化学式为（I）：其中Ar1和Ar2可以相同也可以不同，并且分别独立地选自化学式（II）和（III）的基团：Y1和Z1独立地为CH或NRc+，前提是Y1和Z1中至少有一个为NRc+，并且Y1和Z1中至少有一个为CH，以及在权利要求中定义的Ra、Rb、Rc、X2-和L，或者其水合物或溶剂化合物。还描述了包含上述化合物的组合物和试剂盒。所述的双酰肼衍生物的化学式（I）、组合物和试剂盒可用作药物，特别用于治疗或预防与EB病毒相关的癌症。
• Development of the Smartphone-Assisted Colorimetric Detection of Thorium by Using New Schiff’s Base and Its Applications to Real Time Samples
  作者：Selva Kumar R、S. K. Ashok Kumar、Kari Vijayakrishna、Akella Sivaramakrishna、C. V. S. Brahmmananda Rao、N. Sivaraman、Suban K. Sahoo

  DOI：10.1021/acs.inorgchem.8b02564

  日期：2018.12.17

  ligand L exhibits two absorbance bands at 320 and 375 nm because of ligand-to-ligand charge transfer. Upon interaction with Th4+, L undergoes red shift of both absorption bands and the formation of a new UV–vis band at 335 and 440 nm. The UV–visible spectral studies indicate the formation of a 1:1 host–guest complex between L and Th4+ with an association constant of 4.7 × 103 M–1. The limit of quantification

  本文通过使1,10-菲咯啉-2,9-二乙酰氨基肼与2-羟基萘醛反应，开发了一种新型的Th 4+离子选择性显色传感器（L）。的感测能力大号朝向的Th 4+在装有溶液和纸带进行了研究大号用分光光度法和比色方法。研究了L与各种f-金属离子和其他从s-block和d-block元素中选择的金属离子的选择性相互作用。结果表明，通过比色法在溶液相二甲基亚砜/ H 2 O（7：3，v / v）和纸条法中，L的肉眼可察觉的颜色变化当与Th 4+和Al 3+相互作用时，分别从无色溶液变为黄橙色和浅黄色，而其他金属离子则不发生干扰。由于配体到配体的电荷转移，配体L在320和375 nm处显示两个吸收带。与Th 4+相互作用时，L经历了两个吸收带的红移，并在335和440 nm处形成了新的UV-vis带。紫外可见光谱研究表明，L与Th 4+之间形成了1：1主客体络合物，缔合常数为4.7×10 3 M –1。定量限和检测限发现用于Th
• Highly selective phenanthroline based light-up fluorescent probe for monitoring Zr(IV) in aqueous medium
  作者：R. Selva Kumar、S.K. Ashok Kumar

  DOI：10.1016/j.inoche.2020.108406

  日期：2021.3

  A dual-mode chemosensor based on phenanthroline dicarbohydrazide (L) was synthesized for selective and sensitive monitoring of Zr4+. The selective distinct colorimetric response and a turn-on fluorescence were observed upon interaction of L with Zr4+ in DMSO:water (8:2, v/v) media. The sensor L could form 1:2 stoichiometric complex with Zr4+ with an association constant of 1 × 104 M−1 by using Jobs

  合成了基于菲咯啉二碳酰肼（L）的双模式化学传感器，用于选择性和灵敏地监测Zr 4+。当L与Zr 4+在DMSO：水（8：2，v / v）介质中相互作用时，观察到选择性独特的比色响应和开启荧光。传感器L可以通过Jobs和Benesi-Hilderbrand（BH）方法与Zr 4+形成1：2的化学计量配合物，缔合常数为1×10 4 M -1。该传感器可以在3至8的宽pH范围内工作，而不受其他常见金属离子的干扰。Zr 4+的检出限（LOD）通过紫外可见分光光度法和荧光分光光度法分析发现分别为180 nM和9 nM。1 H NMR和DFT分析证实了L与Zr 4+的结合相互作用。此外，将配体L用于各种水样品中Zr 4+的定量测定。
• Rapid detection strategies for the ultra-level chemosensing of uranyl ions
  作者：Selva Kumar R、Vetriarasu Venkatesan、R. Bhaskar、S. K. Ashok Kumar、Akella Sivaramakrishna、Kari Vijayakrishna、C. V. S. Brahmmananda Rao、N. Sivaraman、Suban K. Sahoo

  DOI：10.1039/d1dt01803e

  日期：——

  various f-block metal ions and other selected metal ions from s- and d-block by colorimetry, UV-visible spectrophotometry, and smartphone integrated red-green-blue (RGB) model in DMSO : H2O (7 : 3, v/v). The pale-yellow colour of L turns to wine-red upon interaction with uranyl ions (UO22+) and yellow-orange in the presence of Th4+, Zr4+, Fe3+, and Lu3+ ions. Other tested metal ions did not show any

  一个简单的和可靠的比色探针Ñ，Ñ ' -双- （4-二乙氨基-2-羟基亚苄基）-1,10-菲咯啉-2,9-二碳酰肼（大号）已经由4-（二乙基氨基）水杨醛与1反应而合成,10-phenanthroline-2,9-dicarbohydrazide。通过比色法、紫外可见分光光度法和智能手机集成的红-绿-蓝 (RGB) 模型，L与各种 f 区金属离子和来自 s 区和 d 区的其他选定金属离子的相互作用来研究L的传感能力。DMSO：H 2 O（7：3，v/v）。L的淡黄色在与铀酰离子 (UO 2 2+ )相互作用后变为酒红色，并在 Th 4+存在下变为黄橙色、Zr 4+、Fe 3+和Lu 3+离子。其他测试的金属离子没有显示L 的任何颜色变化。这种颜色变化为痕量 UO 2 2+离子的选择性和灵敏的视觉检测提供了一种简单、快速和一致的方法，无需任何复杂的仪器。由于配体到配体电荷转移 (LLCT)，传感器L在
• Synthesis and evaluation of 2,9-disubstituted-1,10-phenanthroline derivatives as G-quadruplex binders
  作者：Joana Figueiredo、Israel Carreira-Barral、Roberto Quesada、Jean-Louis Mergny、Carla Cruz

  DOI：10.1016/j.bmc.2022.116971

  日期：2022.11

  development of G4 stabilizing small molecules. Telomeric regions have received special attention in this field since they can fold into several distinct intramolecular G-quadruplexes topologies. Herein, we report the synthesis of 2,9-disubstituted-1,10-phenanthroline derivatives and their ability to stabilize different intramolecular telomeric G4 sequences. We evaluated ligand-induced stabilization, selectivity

  G-四链体 (G4) 结构是能够在富含鸟嘌呤的核酸序列中形成的非经典 DNA/RNA 二级结构。它们存在于人类基因组的几个区域，包括基因启动子、非翻译序列和端粒。由于它们的生物学相关性，G4 结构被认为是重要的药物靶点，特别是对于抗癌疗法，从而导致 G4 稳定小分子的发展。端粒区域在该领域受到特别关注，因为它们可以折叠成几种不同的分子内 G-四链体拓扑。在此，我们报告了 2,9-二取代-1,10-菲咯啉衍生物的合成及其稳定不同分子内端粒 G4 序列的能力。 我们使用荧光共振能量转移 (FRET) 熔融实验和圆二色性 (CD) 评估了配体诱导的稳定性、选择性和特异性。此外，我们评估了配体对两种癌细胞系（A549 和 H1299）和一种健康细胞系（NHDF）的细胞毒性。