N,N-bis[(6-methoxyquinolin-2-yl)methyl]-N’,N’-bis[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]ethylenediamine | 1402556-13-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-bis[(6-methoxyquinolin-2-yl)methyl]-N’,N’-bis[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]ethylenediamine
• 英文别名: 2-[(2-{bis[(6-methoxyquinolin-2-yl)methyl]amino}ethyl){2-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]ethyl}amino]ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS: 1402556-13-1
• 化学式: C₅₆H₇₀N₄O₂₂
• 分子量: 1151.19
• InChiKey: SLVZMQGLGBJPQV-GAWUTDAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  82.0
• 可旋转键数：
  27.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  298.04
• 氢给体数：
  0.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  N,N-bis[(6-methoxyquinolin-2-yl)methyl]-N’,N’-bis[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]ethylenediamine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以91%的产率得到N,N-bis[(6-methoxyquinolin-2-yl)methyl]-N’,N’-bis[2-(b-d-glucopyranosyloxy)ethyl]ethylenediamine
  参考文献：
  名称：

  Quinoline‐Based, Glucose‐Pendant Fluorescent Zinc Probes

  摘要：

  AbstractQuinoline‐based tetradentate ligands with glucose pendants, N,N′‐bis[2‐(β‐d‐glucopyranosyloxy)ethyl]‐N,N′‐bis[(6‐methoxyquinolin‐2‐yl)methyl]ethylenediamine (N,N′‐6‐MeOBQBGEN) and its N,N‐counterpart, N,N‐6‐MeOBQBGEN, have been prepared, and their fluorescence‐spectral changes upon Zn binding were investigated. Upon excitation at 336 nm, N,N′‐6‐MeOBQBGEN showed weak fluorescence (ϕ≈ 0.016) in HEPES buffer (HEPES 50 mM, KCl 100 mM, pH 7.5). In the presence of Zn, N,N′‐6‐MeOBQBGEN exhibited a significant increase in fluorescence (ϕ=0.096) at 414 nm. The fluorescence enhancement is specific for Zn and Cd (ICd/IZn of 50% at 414 nm). On the other hand, N,N‐6‐MeOBQBGEN exhibited a smaller fluorescence enhancement upon Zn complexation (ϕ=0.043, λex=334 nm, λem=407 nm) compared with N,N′‐6‐MeOBQBGEN. Fluorescence microscopic analysis using PC‐12 rat adrenal cells revealed that N,N′‐6‐MeOBQBGEN exhibits a 1.8‐fold higher fluorescence‐signal response to Zn ion concentration compared with sugar‐depleted compound 2 (N,N′‐bis[(6‐methoxyquinolin‐2‐yl)methyl]ethylenediamine), due to its enhanced uptake into cells due to the targeting ability of the attached carbohydrates.

  DOI：

  10.1002/cbdv.201100445
• 作为产物：
  描述：

  在 盐酸 、 potassium carbonate 、 potassium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 121.0h， 生成 N,N-bis[(6-methoxyquinolin-2-yl)methyl]-N’,N’-bis[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]ethylenediamine
  参考文献：
  名称：

  Quinoline‐Based, Glucose‐Pendant Fluorescent Zinc Probes

  摘要：

  AbstractQuinoline‐based tetradentate ligands with glucose pendants, N,N′‐bis[2‐(β‐d‐glucopyranosyloxy)ethyl]‐N,N′‐bis[(6‐methoxyquinolin‐2‐yl)methyl]ethylenediamine (N,N′‐6‐MeOBQBGEN) and its N,N‐counterpart, N,N‐6‐MeOBQBGEN, have been prepared, and their fluorescence‐spectral changes upon Zn binding were investigated. Upon excitation at 336 nm, N,N′‐6‐MeOBQBGEN showed weak fluorescence (ϕ≈ 0.016) in HEPES buffer (HEPES 50 mM, KCl 100 mM, pH 7.5). In the presence of Zn, N,N′‐6‐MeOBQBGEN exhibited a significant increase in fluorescence (ϕ=0.096) at 414 nm. The fluorescence enhancement is specific for Zn and Cd (ICd/IZn of 50% at 414 nm). On the other hand, N,N‐6‐MeOBQBGEN exhibited a smaller fluorescence enhancement upon Zn complexation (ϕ=0.043, λex=334 nm, λem=407 nm) compared with N,N′‐6‐MeOBQBGEN. Fluorescence microscopic analysis using PC‐12 rat adrenal cells revealed that N,N′‐6‐MeOBQBGEN exhibits a 1.8‐fold higher fluorescence‐signal response to Zn ion concentration compared with sugar‐depleted compound 2 (N,N′‐bis[(6‐methoxyquinolin‐2‐yl)methyl]ethylenediamine), due to its enhanced uptake into cells due to the targeting ability of the attached carbohydrates.

  DOI：

  10.1002/cbdv.201100445