N-n-Octyl-1-naphthylmethylamin | 14489-85-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-n-Octyl-1-naphthylmethylamin
• 英文别名: N-(naphthalen-1-ylmethyl)octan-1-amine
• CAS: 14489-85-1
• 化学式: C₁₉H₂₇N
• 分子量: 269.43
• InChiKey: QNWLVGXRHVKZLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-n-Octyl-1-naphthylmethylamin 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 1-(N-Lys-N-octylamino)methylnaphthalene bis(trifluoroacetate)
  参考文献：
  名称：

  Aryl-alkyl-lysines: Membrane-Active Fungicides That Act against Biofilms of Candida albicans

  摘要：

  Mortality due to pathogenic fungi has been exacerbated by the rapid development of resistance to frontline antifungal drugs. Fungicidal compounds with novel mechanisms of action are urgently needed. Aryl-alkyl-lysines, which are membrane-active small molecules, were earlier shown to be broad-spectrum antibacterial agents with potency in vitro and in vivo. Herein, we report the antifungal properties of aryl-alkyl-lysines. After identifying the most active compound (NCK-10), we tested its activity against a panel of clinically relevant pathogenic fungi and examined NCK-10's effect against immature and mature biofilms of Candida albicans. NCK-10 was capable of inhibiting the growth of various species of fungi (including Candida spp., Cryptococcus spp., and Aspergillus fumigatus) at concentrations similar to those of antifungal drugs used clinically. It was observed that polarization and permeability of the fungal cell membrane were compromised upon addition of NCK-10, indicating its mechanism is disruption of the fungal cell membrane. In addition to interfering with the growth of planktonic fungi, NCK-10 demonstrated the ability to both inhibit biofilm formation and reduce the metabolic activity of cells in C. albicans biofilm. Additionally, our compound was capable of crossing the blood brain barrier in an in vitro model, expanding the potential antifungal applications for NCK-10. Overall, aryl-alkyl-lysines were found to be excellent compounds that warrant further investigation as novel antifungal agents.

  DOI：

  10.1021/acsinfecdis.6b00192
• 作为产物：
  描述：

  1-naphthalen-1-yl-N-octylmethanimine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以0.358 g的产率得到N-n-Octyl-1-naphthylmethylamin
  参考文献：
  名称：

  发色团标记的发光铂络合物：合成，结构和光谱性质†

  摘要：

  已合成基于4-羧酰胺-2-苯基喹啉衍生物的配体，其具有可溶的辛基烃链和系留的芳香生色团，从而提供萘基（HL 2），蒽基（HL 3）和pyr基（HL 4）配体变体生色类似物（HL 1）进行比较。配体的1 H NMR光谱研究表明，HL 2和HL 4存在两种不可互换的异构体，而HL 1和HL 3仅存在一种异构体。在HL上支持DFT计算图4表明这两种异构体可能是近等能量的，并且具有较高的交换ca的势垒。100 kJ mol -1。这些新的配体用Pt（II）进行环金属化，得到络合物[Pt（L 1-4）（acac）]（acac =乙酰丙酮酸）。使用多核NMR谱包括具有特征光谱络合物进行了研究195的Pt { 1个显露H} NMR研究δ铂CA。[Pt（L 1-4）（acac）]为-2785 ppm。对[Pt（L 3）（acac）]和[Pt（L 4）进行了X射线晶体学研究）（acac）]，每个都显示了在P

  DOI：

  10.1039/c6dt01335j

文献信息

• Chromophore-labelled, luminescent platinum complexes: syntheses, structures, and spectroscopic properties
  作者：Oliver J. Stacey、Benjamin D. Ward、Simon J. Coles、Peter N. Horton、Simon J. A. Pope

  DOI：10.1039/c6dt01335j

  日期：——

  (acac = acetylacetonate). The spectroscopically characterised complexes were studied using multinuclear NMR spectroscopy including 195Pt1H} NMR studies which revealed δPtca. −2785 ppm for [Pt(L1–4)(acac)]. X-ray crystallographic studies were undertaken on [Pt(L3)(acac)] and [Pt(L4)(acac)], each showing the weakly distorted square planar geometry at Pt(II); the structure of [Pt(L3)(acac)] showed evidence

  已合成基于4-羧酰胺-2-苯基喹啉衍生物的配体，其具有可溶的辛基烃链和系留的芳香生色团，从而提供萘基（HL 2），蒽基（HL 3）和pyr基（HL 4）配体变体生色类似物（HL 1）进行比较。配体的1 H NMR光谱研究表明，HL 2和HL 4存在两种不可互换的异构体，而HL 1和HL 3仅存在一种异构体。在HL上支持DFT计算图4表明这两种异构体可能是近等能量的，并且具有较高的交换ca的势垒。100 kJ mol -1。这些新的配体用Pt（II）进行环金属化，得到络合物[Pt（L 1-4）（acac）]（acac =乙酰丙酮酸）。使用多核NMR谱包括具有特征光谱络合物进行了研究195的Pt 1个显露H} NMR研究δ铂CA。[Pt（L 1-4）（acac）]为-2785 ppm。对[Pt（L 3）（acac）]和[Pt（L 4）进行了X射线晶体学研究）（acac）]，每个都显示了在P
• Aryl-alkyl-lysines: Membrane-Active Fungicides That Act against Biofilms of <i>Candida albicans</i>
  作者：Chandradhish Ghosh、Vikas Yadav、Waleed Younis、Haroon Mohammad、Youssef A. Hegazy、Mohamed N. Seleem、Kaustuv Sanyal、Jayanta Haldar

  DOI：10.1021/acsinfecdis.6b00192

  日期：2017.4.14

  Mortality due to pathogenic fungi has been exacerbated by the rapid development of resistance to frontline antifungal drugs. Fungicidal compounds with novel mechanisms of action are urgently needed. Aryl-alkyl-lysines, which are membrane-active small molecules, were earlier shown to be broad-spectrum antibacterial agents with potency in vitro and in vivo. Herein, we report the antifungal properties of aryl-alkyl-lysines. After identifying the most active compound (NCK-10), we tested its activity against a panel of clinically relevant pathogenic fungi and examined NCK-10's effect against immature and mature biofilms of Candida albicans. NCK-10 was capable of inhibiting the growth of various species of fungi (including Candida spp., Cryptococcus spp., and Aspergillus fumigatus) at concentrations similar to those of antifungal drugs used clinically. It was observed that polarization and permeability of the fungal cell membrane were compromised upon addition of NCK-10, indicating its mechanism is disruption of the fungal cell membrane. In addition to interfering with the growth of planktonic fungi, NCK-10 demonstrated the ability to both inhibit biofilm formation and reduce the metabolic activity of cells in C. albicans biofilm. Additionally, our compound was capable of crossing the blood brain barrier in an in vitro model, expanding the potential antifungal applications for NCK-10. Overall, aryl-alkyl-lysines were found to be excellent compounds that warrant further investigation as novel antifungal agents.