(5-Hydrazinocarbonylmethoxy-naphthalen-1-yloxy)-acetic acid hydrazide | 889953-00-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (5-Hydrazinocarbonylmethoxy-naphthalen-1-yloxy)-acetic acid hydrazide
• 英文别名: 2-[5-(2-Hydrazinyl-2-oxoethoxy)naphthalen-1-yl]oxyacetohydrazide；2-[5-(2-hydrazinyl-2-oxoethoxy)naphthalen-1-yl]oxyacetohydrazide
• CAS: 889953-00-8
• 化学式: C₁₄H₁₆N₄O₄
• 分子量: 304.305
• InChiKey: JNAWPMUQJBVWMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5-Hydrazinocarbonylmethoxy-naphthalen-1-yloxy)-acetic acid hydrazide 、 alpha-酮戊二酸 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Adhesive π-Clamping within Synthetic Multifunctional Pores

  摘要：

  We report the design, synthesis, and evaluation of synthetic multifunctional pores with adhesive, that is, electron-deficient naphthalenediimide (NDI) pi-clamps at their inner surface. We find that, in lipid bilayer membranes, comparable synthetic pores with and without pi-clamps have similar, nanomolar activity. Functional relevance of adhesive pi-clamping within synthetic pores is demonstrated by means of an innovative in situ blocker screening method. The obtained line of experimental evidence includes (a) different blockage efficiency with and without pi-clamps (quantified as clamping factors), (b) increasing clamping factors with increasing blocker charge (supportive ion pairing), and, most importantly, (c) increasing clamping factors with increasing aromatic electron donor-acceptor interactions. The availability of advanced synthetic multifunctional pores with refined active sites is important for practical applications in domains such as drug discovery (enzyme inhibitor screening) and diagnostics (multianalyte sensing).

  DOI：

  10.1021/ja066886+
• 作为产物：
  描述：

  1,5-二羟基萘 在 caesium carbonate 、 肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 12.0h， 生成 (5-Hydrazinocarbonylmethoxy-naphthalen-1-yloxy)-acetic acid hydrazide
  参考文献：
  名称：

  Synthetic pores with sticky π-clamps

  摘要：

  在本报告中，我们描述了具有π-酸性萘二酰亚胺夹具的合成多功能孔的设计、合成、评估和分子动力学模拟。实验证据表明，形成了不稳定但惰性、异质和抗酸动态四聚孔，这些孔对碱和离子强度敏感。阻塞实验揭示，引入芳香电子给体-接受体相互作用使得可以选择性识别孔内的π-碱性插层物。这一突破对于将合成孔应用于多分析物传感器具有重要意义。

  DOI：

  10.1039/b702255g

文献信息

• Screening of π-Basic Naphthalene and Anthracene Amplifiers for π-Acidic Synthetic Pore Sensors
  作者：Shinya Hagihara、Ludovic Gremaud、Guillaume Bollot、Jiri Mareda、Stefan Matile

  DOI：10.1021/ja078256t

  日期：2008.4.1

  Synthetic ion channels and pores attract current attention as multicomponent sensors in complex matrixes. This application requires the availability of reactive signal amplifiers that covalently capture analytes and drag them into the pore. pi-Basic 1,5-dialkoxynaphthalenes (1,5-DAN) are attractive amplifiers because aromatic electron donor-acceptor (AEDA) interactions account for their recognition within pi-acidic naphthalenediimide (NDI) rich synthetic pores. Focusing on amplifier design, we report here the synthesis of a complete collection of DAN and dialkoxyanthracene amplifiers, determine their oxidation potentials by cyclic voltammetry, and calculate their quadrupole moments. Blockage experiments reveal that subtle structural changes in regioisomeric DAN amplifiers can be registered within NDI pores. Frontier orbital overlap in AEDA complexes, oxidation potentials, and, to a lesser extent, quadrupole moments are shown to contribute to isomer recognition by synthetic pores. Particularly important with regard to practical applications of synthetic pores as multianalyte sensors, we further demonstrate that application of the lessons learned with DAN regioisomers to the expansion to dialkoxyanthracenes provides access to privileged amplifiers with submicromolar activity.
• Synthetic pores with sticky π-clamps
  作者：Hiroyuki Tanaka、Guillaume Bollot、Jiri Mareda、Svetlana Litvinchuk、Duy-Hien Tran、Naomi Sakai、Stefan Matile

  DOI：10.1039/b702255g

  日期：——

  In this report, we describe design, synthesis, evaluation and molecular dynamics simulations of synthetic multifunctional pores with π-acidic naphthalenediimide clamps. Experimental evidence is provided for the formation of unstable but inert, heterogeneous and acid-insensitive dynamic tetrameric pores that are sensitive to base and ionic strength. Blockage experiments reveal that the introduction of aromatic electron donor–acceptor interactions provides access to the selective recognition of π-basic intercalators within the pore. This breakthrough is important for the application of synthetic pores as multianalyte sensors.

  在本报告中，我们描述了具有π-酸性萘二酰亚胺夹具的合成多功能孔的设计、合成、评估和分子动力学模拟。实验证据表明，形成了不稳定但惰性、异质和抗酸动态四聚孔，这些孔对碱和离子强度敏感。阻塞实验揭示，引入芳香电子给体-接受体相互作用使得可以选择性识别孔内的π-碱性插层物。这一突破对于将合成孔应用于多分析物传感器具有重要意义。
• Adhesive π-Clamping within Synthetic Multifunctional Pores
  作者：Hiroyuki Tanaka、Svetlana Litvinchuk、Duy-Hien Tran、Guillaume Bollot、Jiri Mareda、Naomi Sakai、Stefan Matile

  DOI：10.1021/ja066886+

  日期：2006.12.1

  We report the design, synthesis, and evaluation of synthetic multifunctional pores with adhesive, that is, electron-deficient naphthalenediimide (NDI) pi-clamps at their inner surface. We find that, in lipid bilayer membranes, comparable synthetic pores with and without pi-clamps have similar, nanomolar activity. Functional relevance of adhesive pi-clamping within synthetic pores is demonstrated by means of an innovative in situ blocker screening method. The obtained line of experimental evidence includes (a) different blockage efficiency with and without pi-clamps (quantified as clamping factors), (b) increasing clamping factors with increasing blocker charge (supportive ion pairing), and, most importantly, (c) increasing clamping factors with increasing aromatic electron donor-acceptor interactions. The availability of advanced synthetic multifunctional pores with refined active sites is important for practical applications in domains such as drug discovery (enzyme inhibitor screening) and diagnostics (multianalyte sensing).