N-((pyren-6-yl)methylene)butane-1-amine | 94869-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N-((pyren-6-yl)methylene)butane-1-amine
• 英文别名: N-Butyl-pyrenyl-(1)-methylenimin；1-Butyliminomethyl-pyren
• CAS: 94869-68-8
• 化学式: C₂₁H₁₉N
• 分子量: 285.389
• InChiKey: LDTYOTITZZZGLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-((pyren-6-yl)methylene)butane-1-amine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 N-(pyren-1-ylmethyl)butan-1-amine
  参考文献：
  名称：

  A prospective antibacterial for drug-resistant pathogens: a dual warhead amphiphile designed to track interactions and kill pathogenic bacteria by membrane damage and cellular DNA cleavage

  摘要：

  合理设计的杀菌双亲化合物可作用于引人注目的目标，并有可能解除致病菌抗药性的产生。

  DOI：

  10.1039/c4cc02354d
• 作为产物：
  描述：

  1-芘甲醛 、 正丁胺 以 甲醇 为溶剂， 以80%的产率得到N-((pyren-6-yl)methylene)butane-1-amine
  参考文献：
  名称：

  A prospective antibacterial for drug-resistant pathogens: a dual warhead amphiphile designed to track interactions and kill pathogenic bacteria by membrane damage and cellular DNA cleavage

  摘要：

  合理设计的杀菌双亲化合物可作用于引人注目的目标，并有可能解除致病菌抗药性的产生。

  DOI：

  10.1039/c4cc02354d

文献信息

• Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates
  作者：Jarosław Lewkowski、Maria Rodriguez Moya、Anna Wrona-Piotrowicz、Janusz Zakrzewski、Renata Kontek、Gabriela Gajek

  DOI：10.3762/bjoc.12.117

  日期：——

  A large series of variously substituted amino(pyren-1-yl)methylphosphonic acid derivatives was synthesized using a modified aza-Pudovik reaction in 20–97% yields. The fluorescence properties of the obtained compounds were investigated revealing that N-alkylamino(pyren-1-yl)methylphosphonic derivatives are stronger emissive compounds than the corresponding N-aryl derivatives. N-Benzylamino(pyren-1-yl)methylphosphonic acid displayed strong fluorescence (Φ_F = 0.68) in phosphate-buffered saline (PBS). The influence of a series of derivatives on two colon cancer cell lines HT29 and HCT116 was also investigated. The most promising results were obtained for N-(4-methoxyphenyl)amino(pyren-1-yl)methylphosphonate, which was found to be cytotoxic for the HCT116 cancer cell line (IC₅₀ = 20.8 μM), simultaneously showing weak toxicity towards normal lymphocytes (IC₅₀ = 230.8 µM).

  使用改良的aza-Pudovik反应合成了一大系列不同取代氨基(芘-1-基)甲基膦酸衍生物，产率在20%至97%之间。研究了所得化合物的荧光性质，发现N-烷基氨基(芘-1-基)甲基膦酸衍生物比相应的N-芳基衍生物具有更强的发光性。N-苄基氨基(芘-1-基)甲基膦酸在磷酸盐缓冲盐水溶液中显示出强烈的荧光(ΦF = 0.68)。还研究了一系列衍生物对结肠癌细胞系HT29和HCT116的影响。最有希望的结果是对HCT116癌细胞系具有细胞毒性的N-(4-甲氧基苯基)氨基(芘-1-基)甲基膦酸酯，其IC50值为20.8μM，同时对正常淋巴细胞显示出微弱毒性(IC50 = 230.8µM)。
• Piperazine-based simple structure for selective sensing of Hg2+ and glutathione and construction of a logic circuit mimicking an INHIBIT gate
  作者：Kumaresh Ghosh、Debojyoti Tarafdar、Asmita Samadder、Anisur Rahman Khuda-Bukhsh

  DOI：10.1039/c3nj00855j

  日期：——

  A simple chemosensor (1) has been designed and synthesized. The chemosensor selectively recognizes Hg2+ ions in THF–H2O (3 : 1, v/v) by showing a significant increase in emission and a bluish color of the solution under exposure to UV light. Change of the fluorophore unit in 1 leads to 2, which also shows selective sensing of Hg2+ under similar conditions. Furthermore, while the ensemble of 1 with Hg2+ selectively senses reduced glutathione (GSH) over cysteine and homocysteine, the ensemble of 2 with Hg2+ has been observed to be inefficient to distinguish glutathione from other biothiols. Thus probe 1 and inputs Hg2+ and GSH can be used to develop an INHIBIT logic gate.

  一种简单的化学传感器（1）已被设计和合成。该传感器能选择性识别THF–H2O（3 : 1，v/v）中的Hg2+离子，在紫外光照射下显示出明显增强的发射和溶液的蓝色变化。传感器1中的荧光团单元的变化导致了2的产生，该传感器在相似条件下也显示出选择性感应Hg2+。此外，传感器1与Hg2+的复合物能够选择性地识别还原型谷胱甘肽（GSH），而对半胱氨酸和同半胱氨酸则不敏感，而与Hg2+的复合物2则被观察到对谷胱甘肽和其他生物硫醇的区分能力较差。因此，探针1及其输入Hg2+和GSH可用于开发一个抑制逻辑门。
• Pyrenyl-imino-C2-glucosyl conjugate: synthesis, characterization, and ratiometric and reversible OFF–ON receptor for Hg2+
  作者：Sivaiah Areti、Vijaya Kumar Hinge、Chebrolu P. Rao

  DOI：10.1016/j.carres.2014.06.014

  日期：2014.11

  A pyrenyl-imino-C2-glucosyl conjugate, L, has been synthesized and characterized. The L exhibits selective chromogenic as well as fluorescent property towards Hg2+ in a ratiometric manner by showing similar to 30 fold enhanced fluorescence emission intensity. The fluorescence enhancement continues to be there even in the presence of thirteen other competitive metal ions studied. The sensing of Hg2+ is well demonstrated using various techniques, such as, fluorescence, absorption, visual color under UV light and ESI MS. A minimum detection limit of 18 +/- 2 ppb was shown by L for Hg2+ in ethanol. All the experimental studies carried out supported the formation of 2:1 complex between L and Hg2+. The structure of the 2:1 complex was modeled at ab initio using HF and found a structure where Hg2+ is sandwiched between the two pyrenyl moieties. The reversibility and reusability of L has been demonstrated using fluoride ion. (C) 2014 Elsevier Ltd. All rights reserved.