2-碘-N-(1,10-菲咯啉-5-基)乙酰胺 | 111047-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 中文名称: 2-碘-N-(1,10-菲咯啉-5-基)乙酰胺
• 英文名称: 2-iodo-N-1,10-phenanthrolin-5-ylacetamide
• 英文别名: 5-iodoacetamido-1,10-phenanthroline；5-Iodoacetamidophenanthroline；IA-Phen；2-Iodo-N-(1,10-phenanthrolin-5-YL)acetamide
• CAS: 111047-29-1
• 化学式: C₁₄H₁₀IN₃O
• 分子量: 363.157
• InChiKey: VNZCYEFHRZCOGS-UHFFFAOYSA-N

物化性质

• 熔点：
  180 °C (decomp)(Solv: chloroform (67-66-3))
• 沸点：
  591.5±40.0 °C(Predicted)
• 密度：
  1.852±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  、 2-碘-N-(1,10-菲咯啉-5-基)乙酰胺 在 碳酸氢钠 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Synthese et reactivite d'oligothymidylates substitues par un agent intercalant et un groupe thiophosphate

  摘要：

  DOI：

  10.1016/s0040-4039(00)95565-5
• 作为产物：
  描述：

  5-硝基-1,10-菲咯啉 在 palladium on activated charcoal 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-碘-N-(1,10-菲咯啉-5-基)乙酰胺
  参考文献：
  名称：

  Synthesis and characterisation of a new DNA-binding bifunctional ruthenium(II) complex

  摘要：

  一种新的DNA结合分子Ru(tap)2POQ2+已经被合成并表征，其中多吡啶金属钌(II)复合物通过一个灵活的链连接到氨基氯喹。这一复合物被视为双功能，因为它包含两种不同结合模式和光反应性的部分。该化合物的1H NMR数据表明两种分子物种之间存在平衡。Ru(tap)2POQ2+的光谱特性在吸收和荧光方面进行了检查，并与不包含氨基氯喹部分的相应钌(II)复合物Ru(tap)2phen2+进行了比较。相对量子产率和寿命显示，MLCT激发态行为受到连结喹啉的影响。平衡中两种物种之一的分子内光诱导电子转移被认为是导致钌(II)复合物荧光猝灭的原因。基于荧光和热变性研究，报告了Ru(tap)2POQ2+与DNA及[poly(d[A-T])]2的结合特性初步结果。当Ru(tap)2POQ2+与核酸相互作用时，其分子内荧光猝灭受到抑制。因此，在存在多核苷酸时所产生的发射相比于参考复合物Ru(tap)2phen2+观察到的荧光增强更加显著。

  DOI：

  10.1039/ft9938903261

文献信息

• ATP- and Iron−Protein-Independent Activation of Nitrogenase Catalysis by Light
  作者：Lauren E. Roth、Joey C. Nguyen、F. Akif Tezcan

  DOI：10.1021/ja1071866

  日期：2010.10.6

  molybdenum-iron-protein (MoFeP) of nitrogenase for substrate reduction independent of ATP hydrolysis and the iron-protein (FeP), which have been believed to be essential for catalytic turnover. A MoFeP variant labeled on its surface with a Ru-photosensitizer is shown to photocatalytically reduce protons and acetylene, most likely at its active site, FeMoco. The uncoupling of nitrogenase catalysis from ATP hydrolysis

  我们在此报告固氮酶的钼铁蛋白 (MoFeP) 的光驱动激活，用于底物还原，而与 ATP 水解和铁蛋白 (FeP) 无关，铁蛋白 (FeP) 被认为对催化转化至关重要。在其表面用 Ru 光敏剂标记的 MoFeP 变体显示出光催化还原质子和乙炔，最有可能在其活性位点 FeMoco。固氮酶催化与 ATP 水解的解偶联应该能够研究 MoFeP 内的氧化还原动力学和用于结构研究的离散反应中间体群体。
• Characterisation of bifunctional ruthenium(II) complexes, potential DNA photo-probes. Presence of folded and unfolded conformers †
  作者：André Del Guerzo、Andrée Kirsch-De Mesmaeker、Martine Demeunynck、Jean Lhomme

  DOI：10.1039/b000197j

  日期：——

  Novel bifunctional ruthenium(II) complexes, [Ru(TAP)2(POQ-Nmet)]2+ and [Ru(BPY)2(POQ-Nmet)]2+ (1a, 2a), containing a metallic and an organic moiety, have been prepared as photoprobes and photoreagents of DNA (TAP = 1,4,5,8-tetraazaphenanthrene, POQ-Nmet = 5-[6-(7-chloroquinolin-4-yl)-3-thia-6-azaheptanamido]-1,10-phenanthroline). The ES mass spectrometry and 1H NMR data in organic solvents indicate that the quinoline moiety exists in both the protonated and non-protonated form. Moreover, the comparison of the NMR data with those of the corresponding monofunctional complexes (without quinoline) evidences that [Ru(TAP)2(POQ-Nmet)]2+ and [Ru(BPY)2(POQ-Nmet)]2+ are unfolded when the quinoline unit is protonated whereas deprotonation permits folding of the molecule. In the folded state the spatial proximity of the electron donor (the organic moiety) and electron acceptor (the metallic moiety) in [Ru(TAP)2(POQ-Nmet)]2+ favours intramolecular photo-induced electron transfer, which has been shown in a previous study to be responsible for the very low luminescence of 1a in non-protonating solutions. The restoration of the luminescence by protonation of the quinoline moiety as observed previously is in agreement with the unfolding of the molecule demonstrated in this work. The existence of such folding–unfolding processes related to protonation is crucial for studies of 1a with DNA.

  新型双功能钌(II)配合物，[Ru(TAP)2(POQ-Nmet)]2+ 和 [Ru(BPY)2(POQ-Nmet)]2+ (1a, 2a)，含有金属和有机部分，已被制备为DNA的光探针和光试剂（TAP=1,4,5,8-四氮杂菲，POQ-Nmet=5-[6-(7-氯喹啉-4-基)-3-thia-6-氮杂庚酰胺] -1,10-菲咯啉）。有机溶剂中的ES质谱和1H NMR数据表明喹啉部分以质子化和非质子化形式存在。此外，NMR数据与相应单官能配合物（不含喹啉）的比较证明[Ru(TAP)2(POQ-Nmet)]2+和[Ru(BPY)2(POQ-Nmet)]2+当喹啉单元质子化时，分子折叠，而去质子化允许分子折叠。在折叠状态下，[Ru(TAP)2(POQ-Nmet)]2+ 中电子供体（有机部分）和电子受体（金属部分）的空间接近性有利于分子内光诱导电子转移，这已被证实先前的研究显示，1a 在非质子化溶液中发光非常低。如先前所观察到的，通过喹啉部分的质子化恢复发光与本工作中演示的分子的展开一致。这种与质子化相关的折叠-展开过程的存在对于 DNA 1a 的研究至关重要。
• Method for fabricating two-dimensional protein crystals
  申请人：The Regents of the University of California

  公开号：US11286277B2

  公开（公告）日：2022-03-29

  Polypeptide assemblies and building blocks and methods for making them are provided.

  提供了多肽组件和构建模块以及制造它们的方法。
• A Superprotein Triangle Driven by Nickel(II) Coordination: Exploiting Non-Natural Metal Ligands in Protein Self-Assembly
  作者：Robert J. Radford、F. Akif Tezcan

  DOI：10.1021/ja9000695

  日期：2009.7.8

  We previously devised a strategy (metal-directed protein self-assembly, MDPSA) that utilizes the simultaneous stability, lability, and directionality of metal-ligand bonds to drive protein-protein interactions. Here we show that both the structural and functional scopes of MDPSA can be broadened by incorporation of non-natural metal-chelating ligands onto protein surfaces. A cytochrome cb(562) variant, MBP-Phen1, which features a covalently attached phenanthroline (Phen) group on its surface, self-assembles into an unusual triangular architecture (Ni-3:MBP-Phen1(3)) upon binding Ni as a result of specific Phen-protein interactions. The crystal structure of Ni-3:MBP-Phen1(3) reveals that the Phen group is buried in a small pocket on the protein surface, which results in an unsaturated Ni coordination environment.
• Synthesis and characterisation of N-1,10-phenanthrolin-5-ylalkylamides and their photosensitising heteroleptic Ru(II) complexes
  作者：Pedro Ramiro、David García-Fresnadillo、Guillermo Orellana

  DOI：10.1016/j.tet.2005.08.012

  日期：2005.10

  In the context of our studies on ruthenium(II) complexes containing polyazaheterocyclic ligands as functionalised photosensitisers for singlet molecular oxygen generation in heterogeneous phase, we describe the synthesis and spectroscopic characterisation of different amide-functionalised N-1, 10-phenanthrolin-5-ylalkylamides. These chelators are used to obtain heteroleptic [Ru(phen)(2)L](2+) complexes, where L stands for 2-iodo-N-1,10-phenanthrolin-5-ylacetamide (5-iap), 4-oxo-4-(1,10-phenanthrolin-5ylamino)butanoic acid (5-suap), 5-oxo-5-(1,10-phenanthrolin-5-ylamino)pentanoic acid (5-glap) and tert-butyl 4-oxo-4-(1,10-phenanthrolin-5-ylamino)butylcarbamate (BOC-5-ngap). The spectroscopic data, excited state lifetimes and quenching rate constants with O-2 (ca. 3.7 X 10(9) L mol(-1) s(-1)) of these novel complexes are also reported. (c) 2005 Elsevier Ltd. All rights reserved.