N-(1H-benzimidazol-2-ylmethyl)-2-[1-[2-[2-(1H-benzimidazol-2-ylmethylamino)-2-oxoethoxy]naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxyacetamide | 1351952-57-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-(1H-benzimidazol-2-ylmethyl)-2-[1-[2-[2-(1H-benzimidazol-2-ylmethylamino)-2-oxoethoxy]naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxyacetamide
• CAS: 1351952-57-2
• 化学式: C₄₀H₃₂N₆O₄S
• 分子量: 692.798
• InChiKey: ZGDKBRJEMIYMOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  51
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,1'-硫联二(2-萘酚) 在 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 36.5h， 生成 N-(1H-benzimidazol-2-ylmethyl)-2-[1-[2-[2-(1H-benzimidazol-2-ylmethylamino)-2-oxoethoxy]naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxyacetamide
  参考文献：
  名称：

  Benzimidazole Conjugate of 1,1′-Thiobis(2-naphthol) as Switch-On Fluorescence Receptor for Ag⁺ and the Complex as Secondary Recognition Ensemble toward Cys, Asp, and Glu in Aqueous Methanolic Solution: Synthesis, Characterization, Ion and Amino Acid Recognition, Computational Studies, and Microscopy Features

  摘要：

  A new 1,1'-thiobis(2-naphthoxy)-based receptor molecule (L) containing a benzimidazole moiety has been synthesized and characterized by H-1 NMR, ESI-MS, and elemental analysis. The selectivity of L has been explored in aqueous methanol, resulting in selective (7.5 +/- 0.5)-fold switch-on fluorescence response toward Ag+ among 14 different transition, alkali, and alkaline earth metal ions studied. The complexation of Ag+ by L has been addressed by ESI-MS, H-1 NMR, and UV-vis spectra. Microstructural features of L and its Ag+ complex have been measured by AFM and TEM. The morphological features of L alone and L in the presence of Ag+ differ dramatically both in shape and size, and the ion induces the formation of chains owing to its coordinating ability toward benzimidazole. Further, the in situ [Ag+-L] complex was titrated against 20 naturally occurring amino acids and found that this complex acts as a secondary recognition ensemble toward Cys, Asp, and Glu by switch-off fluorescence.

  DOI：

  10.1021/jo201926q

文献信息

• Benzimidazole Conjugate of 1,1′-Thiobis(2-naphthol) as <i>Switch-On</i> Fluorescence Receptor for Ag⁺ and the Complex as Secondary Recognition Ensemble toward Cys, Asp, and Glu in Aqueous Methanolic Solution: Synthesis, Characterization, Ion and Amino Acid Recognition, Computational Studies, and Microscopy Features
  作者：Jayaraman Dessingou、Atanu Mitra、Khatija Tabbasum、Garima Singh Baghel、Chebrolu P. Rao

  DOI：10.1021/jo201926q

  日期：2012.1.6

  A new 1,1'-thiobis(2-naphthoxy)-based receptor molecule (L) containing a benzimidazole moiety has been synthesized and characterized by H-1 NMR, ESI-MS, and elemental analysis. The selectivity of L has been explored in aqueous methanol, resulting in selective (7.5 +/- 0.5)-fold switch-on fluorescence response toward Ag+ among 14 different transition, alkali, and alkaline earth metal ions studied. The complexation of Ag+ by L has been addressed by ESI-MS, H-1 NMR, and UV-vis spectra. Microstructural features of L and its Ag+ complex have been measured by AFM and TEM. The morphological features of L alone and L in the presence of Ag+ differ dramatically both in shape and size, and the ion induces the formation of chains owing to its coordinating ability toward benzimidazole. Further, the in situ [Ag+-L] complex was titrated against 20 naturally occurring amino acids and found that this complex acts as a secondary recognition ensemble toward Cys, Asp, and Glu by switch-off fluorescence.