16-Hexadecoxy-2,13-dimethyl-3,6,9,12,18-pentazabicyclo[12.3.1]octadeca-1(17),14(18),15-triene | 1526921-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 16-Hexadecoxy-2,13-dimethyl-3,6,9,12,18-pentazabicyclo[12.3.1]octadeca-1(17),14(18),15-triene
• 英文别名: 16-hexadecoxy-2,13-dimethyl-3,6,9,12,18-pentazabicyclo[12.3.1]octadeca-1(17),14(18),15-triene
• CAS: 1526921-38-9
• 化学式: C₃₁H₅₉N₅O
• 分子量: 517.842
• InChiKey: VDEUUNOCKAMUBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  70.2
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氯-2,6-二酰基吡啶 在 四丁基溴化铵 、 氢溴酸 、 对甲苯磺酸 、 sodium hydroxide 、 manganese(ll) chloride 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 56.5h， 生成 16-Hexadecoxy-2,13-dimethyl-3,6,9,12,18-pentazabicyclo[12.3.1]octadeca-1(17),14(18),15-triene
  参考文献：
  名称：

  Amphiphilic Pentaazamacrocyclic Manganese Superoxide Dismutase Mimetics

  摘要：

  Five newly functionalized pentaazamacrocyclic manganese complexes, with variable lengths and amounts of the aliphatic groups (three compounds with one linear chain containing 12, 16, and 22 carbon atoms, i.e., MnL1, MnL2, and MnL3, respectively, as well as two compounds containing two C12 and C16 chains, MnL4 and MnL5, respectively) that are derivatives of the known SOD mimetic, Mn(Me-2-Pyane), have been synthesized. These amphiphilic complexes were characterized by the ESI mass spectrometry, potentiometric titrations, light scattering, cyclic voltammetry, and direct stopped-flow determination of their SOD activity at pH 8.1 and 7.4 (in phosphate and HEPES buffers). The formation of supra-molecular aggregates that predominantly exist in the solution as a defined micellar/nanostructure assembly, with an average 400 nm size, has been demonstrated for MnL1. The biological effects of the selected complexes (MnL1 and MnL2) on the superoxide level in cytosol and mitochondria have been tested, as well as their effects on the prevention of the lipid peroxidation induced by paraquat. Advantages and disadvantages of the lipophilic pentaazamacrocyclic manganese SOD mimetics in comparison to the corresponding nonsubstituted SOD active complex have been discussed.

  DOI：

  10.1021/ic402469t

文献信息

• Amphiphilic Pentaazamacrocyclic Manganese Superoxide Dismutase Mimetics
  作者：Dominik Lieb、Isabell Kenkell、Jan Lj. Miljković、Daniel Moldenhauer、Nadine Weber、Milos R. Filipović、Franziska Gröhn、Ivana Ivanović-Burmazović

  DOI：10.1021/ic402469t

  日期：2014.1.21

  Five newly functionalized pentaazamacrocyclic manganese complexes, with variable lengths and amounts of the aliphatic groups (three compounds with one linear chain containing 12, 16, and 22 carbon atoms, i.e., MnL1, MnL2, and MnL3, respectively, as well as two compounds containing two C12 and C16 chains, MnL4 and MnL5, respectively) that are derivatives of the known SOD mimetic, Mn(Me-2-Pyane), have been synthesized. These amphiphilic complexes were characterized by the ESI mass spectrometry, potentiometric titrations, light scattering, cyclic voltammetry, and direct stopped-flow determination of their SOD activity at pH 8.1 and 7.4 (in phosphate and HEPES buffers). The formation of supra-molecular aggregates that predominantly exist in the solution as a defined micellar/nanostructure assembly, with an average 400 nm size, has been demonstrated for MnL1. The biological effects of the selected complexes (MnL1 and MnL2) on the superoxide level in cytosol and mitochondria have been tested, as well as their effects on the prevention of the lipid peroxidation induced by paraquat. Advantages and disadvantages of the lipophilic pentaazamacrocyclic manganese SOD mimetics in comparison to the corresponding nonsubstituted SOD active complex have been discussed.