N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-quinolinecarboxamide | 959398-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-quinolinecarboxamide
• 英文别名: N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-quinaldine-2-carboxamide；N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-quinoline-2-carboxamide；PaPy2QH；N-[2-[bis(pyridin-2-ylmethyl)amino]ethyl]quinoline-2-carboxamide
• CAS: 959398-18-6
• 化学式: C₂₄H₂₃N₅O
• 分子量: 397.48
• InChiKey: IQDJPOJEMIZMLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-quinolinecarboxamide 、 manganese(II) perchlorate hexahydrate 在 NaH 作用下， 以 乙醇 为溶剂， 以52%的产率得到[Mn(N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-quinoline-2-carboxamide)(H2O)]ClO4
  参考文献：
  名称：

  近红外光激活从设计的光活性亚硝基锰中释放一氧化氮：作为 NO 供体的策略、设计和潜力

  摘要：

  衍生自五齿配体 N,N-双（2-吡啶基甲基）胺-N-乙基-2-喹啉-2-甲酰胺的两种新锰配合物，PaPy2QH，其中 H 是可解离的质子），即 [Mn(PaPy2Q)( NO)]ClO4 (2) 和 [Mn(PaPy2Q)(OH)]ClO4 (3) 已经合成并进行了结构表征。Mn(III) 络合物 [Mn(PaPy2Q)(OH)]ClO4 (3)，虽然对分子氧不敏感，但与一氧化氮 (NO) 反应生成亚硝酰基络合物 [Mn(PaPy2Q)(NO)]ClO4 (2)通过还原亚硝基化。这种抗磁性 {Mn-NO}6 亚硝酰基在 1725 cm-1 处显示出 nuNO，并且高度溶于水，λmax 位于 500 和 670 nm。将 2 溶液暴露于近红外 (NIR) 光 (810 nm, 4 mW) 会导致栗色溶液漂白并通过 NO 敏感电极检测游离 NO。量子产率 2 (Phi = 0.694 +/- 0

  DOI：

  10.1021/ja710265j

文献信息

• Controlling the Reactivity of a Metal-Hydroxo Adduct with a Hydrogen Bond
  作者：Adedamola A. Opalade、Logan Hessefort、Victor W. Day、Timothy A. Jackson

  DOI：10.1021/jacs.1c06199

  日期：2021.9.22

  (MnLOX) and manganese superoxide dismutase (MnSOD) utilize mononuclear Mn centers to effect their catalytic reactions. In the oxidized MnIII state, the active site of each enzyme contains a hydroxo ligand, and X-ray crystal structures imply a hydrogen bond between this hydroxo ligand and a cis carboxylate ligand. While hydrogen bonding is a common feature of enzyme active sites, the importance of this

  锰脂氧合酶 (MnLOX) 和锰超氧化物歧化酶 (MnSOD) 利用单核 Mn 中心来影响它们的催化反应。在氧化的 Mn III状态下，每种酶的活性位点都包含一个羟基配体，X 射线晶体结构暗示该羟基配体和顺式羧酸盐配体之间存在氢键。虽然氢键是酶活性位点的一个共同特征，但这种特殊的羟基-羧酸盐相互作用的重要性相对来说还没有被探索过。在本研究中，我们检查了一对仅由一个官能团不同的 Mn III -羟基配合物。这些配合物之一，[Mn III (OH)(PaPy 2 N)] +，含有能够与羟基配体形成分子内氢键的萘啶基部分。第二种配合物 [Mn III (OH)(PaPy 2 Q)] +含有一个不允许任何分子内氢键合的喹啉基部分。这些配合物的光谱表征支持一个共同的结构，但对[Mn III (OH)(PaPy 2 N)] +有扰动，与氢键一致。使用具有活化 O-H 键的各种底物的动力学研究表明，[Mn
• Formation of a triply bridged µ-oxo diiron(iii) core stabilized by two deprotonated carboxamide groups upon photorelease of NO from a {Fe–NO}6 iron nitrosyl
  作者：Aura A. Eroy-Reveles、C. Gianna Hoffman-Luca、Pradip K. Mascharak

  DOI：10.1039/b710076k

  日期：——

  The iron nitrosyl [(PaPy2Q)Fe(NO)](ClO4)2 (2), derived from the quinoline-based ligand PaPy2QH (N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-quinoline-2-carboxamide, where H is dissociable proton) has been characterized by spectroscopy and X-ray diffraction techniques. The 1H NMR spectrum (S = 0 ground state) and νNO value of 1885 cm−1 indicate that 2 is a Fe–NO}6 nitrosyl. Although 2 is stable in the dark, exposure of an acetonitrile solution of 2 (λmax = 510 nm) to light in the visible range causes rapid release of NO and formation of the solvato species [(PaPy2Q)Fe(MeCN)](ClO4)2 (6). Quantum yield (Φ) measurements indicate that 2 is a more efficient NO donor (Φ = 0.258) than [(PaPy3)Fe(NO)](ClO4)2 (1, Φ = 0.185), a complex derived from a similar but pyridine-based ligand. Interestingly, when the photoproduct 6 is exposed to water or a small amount of base, the triply bridged diiron(III) species [(PaPy2Q)FeOFe(PaPy2Q)](ClO4)2 (3) forms in good yield. This species can be independently synthesized from aerobic oxidation of the Fe(II) species [(PaPy2Q)Fe(MeCN)](ClO4) in acetonitrile. The structure of 3 reveals a unique Fe(III)–O–Fe(III) link supported by two (η2,µ2)µ-NCO bridges derived from the carboxamido groups of the two (PaPy2Q)Fe(III) moieties.

  亚硝酰铁 [(PaPy2Q)Fe(NO)](ClO4)2 (2)，源自喹啉基配体 PaPy2QH (N,N-双(2-吡啶基甲基)胺-N-乙基-2-喹啉-2 -甲酰胺，其中H是可解离的质子）已通过光谱学和X射线衍射技术进行了表征。 1H NMR 谱（S = 0 基态）和 1885 cm-1 的 πNO 值表明 2 是一个 Fe-NO}6 亚硝酰基。尽管 2 在黑暗中稳定，但将 2 的乙腈溶液 (Δmax = 510 nm) 暴露在可见光范围内会导致 NO 快速释放并形成溶剂化物 [(PaPy2Q)Fe(MeCN)]( ClO4)2 (6)。量子产率 (Δ) 测量表明 2 是比 [(PaPy3)Fe(NO)](ClO4)2 (1, Δ = 0.185) 更有效的 NO 供体 (Δ = 0.258)，[(PaPy3)Fe(NO)](ClO4)2 (1, Δ = 0.185) 是一种源自类似但基于吡啶的配体。有趣的是，当光产物 6 暴露于水或少量碱时，三桥联二铁 (III) 物质 [(PaPy2Q)FeOFe(PaPy2Q)](ClO4)2 (3) 会以良好的产率形成。该物质可以通过 Fe(II) 物质 [(PaPy2Q)Fe(MeCN)](ClO4) 在乙腈中的有氧氧化独立合成。 3 的结构揭示了独特的 Fe(III)–O–Fe(III) 连接，该连接由两个 (PaPy2Q)Fe(III) 的羧酰胺基衍生的两个 (β2,µ2)µ-NCO 桥支撑。 ) 部分。
• Photoactive ruthenium nitrosyls derived from quinoline- and pyridine-based ligands: Accelerated photorelease of NO due to quinoline ligation
  作者：Michael J. Rose、Marilyn M. Olmstead、Pradip K. Mascharak

  DOI：10.1016/j.poly.2007.03.010

  日期：2007.10

  The ruthenium nitrosyl [(PaPy(2)Q)Ru(NO)](BF4)(2), derived from the quinoline-based ligand PaPy(2)QH (PaPy(2)QH = N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-quinaldine-2-carboxamide; H = dissociable proton) has been synthesized and characterized by X-ray crystallography and spectroscopic techniques. This Ru-NO}(6) nitrosyl is soluble in aqueous media and stable under physiological conditions at pH 7. [(PaPy(2)Q)Ru(NO)](2+) releases NO rapidly upon exposure to low-intensity UV light (5 mW/cm(2)). The NO donor capacity of this nitrosyl (quantum yield = 0.20, lambda(irr) = 365 nm) is considerably higher than that of analogous nitrosyl derived from a polypyridyl ligand without the quinoline moiety. (c) 2007 Elsevier Ltd. All rights reserved.
• Composite Materials Containing Structural Polymers and Photoreactive Nitric Oxide Releasing Agents and Uses Thereof for Wound Dressings
  申请人：Marquette University

  公开号：US20190240372A1

  公开（公告）日：2019-08-08

  Disclosed herein are composite materials, ionic liquid compositions for preparing the composite materials, and methods for using the composite materials prepared from the ionic liquid compositions. The composite materials typically include structural polymers and nitric oxide releasing agents, and preferably photo-reactive nitric oxide releasing compounds or complexes. The composite materials may be prepared from ionic liquid compositions comprising the structural polymers and the nitric oxide releasing agent, where the ionic liquid is removed from the ionic liquid compositions to obtain the composite materials. The composite materials may be used in applications include dressing for wounds, where the nitric oxide releasing agents may be induced to release nitric oxide in order to inhibit microbial growth and promote healing.
• [EN] COMPOSITE MATERIALS CONTAINING STRUCTURAL POLYMERS AND PHOTOREACTIVE NITRIC ODIDE RELEASING AGENTS AND USES THEREOF FOR WOUND DRESSINGS<br/>[FR] MATÉRIAUX COMPOSITES CONTENANT DES POLYMÈRES STRUCTURAUX ET DES AGENTS DE LIBÉRATION D'OXYDE NITRIQUE PHOTORÉACTIFS ET LEURS UTILISATIONS POUR PANSEMENTS DE PLAIES
  申请人：UNIV MARQUETTE

  公开号：WO2018075614A1

  公开（公告）日：2018-04-26

  Disclosed herein are composite materials, ionic liquid compositions for preparing the composite materials, and methods for using the composite materials prepared from the ionic liquid compositions. The composite materials typically include structural polymers and nitric oxide releasing agents, and preferably photo-reactive nitric oxide releasing compounds or complexes. The composite materials may be prepared from ionic liquid compositions comprising the structural polymers and the nitric oxide releasing agent, where the ionic liquid is removed from the ionic liquid compositions to obtain the composite materials. The composite materials may be used in applications include dressing for wounds, where the nitric oxide releasing agents may be induced to release nitric oxide in order to inhibit microbial growth and promote healing.