diethyl-2,2'-(propane-1,3-diylbis((2-hydroxy-3-methoxybenzyl)azanediyl))diacetate | 1421749-23-6

• 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: diethyl-2,2'-(propane-1,3-diylbis((2-hydroxy-3-methoxybenzyl)azanediyl))diacetate
• 英文别名: Ethyl 2-[3-[(2-ethoxy-2-oxoethyl)-[(2-hydroxy-3-methoxyphenyl)methyl]amino]propyl-[(2-hydroxy-3-methoxyphenyl)methyl]amino]acetate；ethyl 2-[3-[(2-ethoxy-2-oxoethyl)-[(2-hydroxy-3-methoxyphenyl)methyl]amino]propyl-[(2-hydroxy-3-methoxyphenyl)methyl]amino]acetate
• CAS: 1421749-23-6
• 化学式: C₂₇H₃₈N₂O₈
• 分子量: 518.607
• InChiKey: LCUKOJMYWQLCQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  37
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  邻香草醛 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 34.0h， 生成 diethyl-2,2'-(propane-1,3-diylbis((2-hydroxy-3-methoxybenzyl)azanediyl))diacetate
  参考文献：
  名称：

  Salen, reduced salen and N-alkylated salen type compounds: Spectral characterization, theoretical investigation and biological studies

  摘要：

  Salen [2,2'-{propane-1,3-diylbis[nitrilo(E)methylylidene]}bis(6-methoxyphenol)], reduced salen [(2,2'-[propane-1,3-diylbis(iminomethylene))]bis(6-methoxyphenol)] and N-alkylated salen [diethyl-2,2'-(propane-1,3-diylbis((2-hydroxy-3-methoxybenzyl) azanediyl))diacetate] compounds have been synthesized and characterized by IR, H-1 NMR, C-13 NMR and UV-vis. spectroscopy. Molecular geometry of the title compounds in the ground state has been optimized by density functional method (B3LYP) with 6-31G basis set. Vibrational frequencies of the compounds were computed and compared with the experimental values. Tautomeric stability study of salen inferred that the enolimine form is more stable than its keto-enamine form in gas phase. The spectral behavior of salen in polar and nonpolar solvents was examined demonstrate the positive solvatochromism. The synthesized compounds have been studied with respect to their binding to calf thymus DNA showed that there were interactions between the compounds and DNA through a groove binding mode. Furthermore, the DNA cleavage activity of the compounds has been investigated by gel electrophoresis. The antioxidant properties of compounds were evaluated by DPPH method. The N-alkylated compound has a higher DPPH free radical scavenging activity. The antimicrobial activity was investigated on various gram positive and gram negative bacteria. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.11.100

文献信息

• Salen, reduced salen and N-alkylated salen type compounds: Spectral characterization, theoretical investigation and biological studies
  作者：P. Jeslin Kanaga Inba、B. Annaraj、S. Thalamuthu、M.A. Neelakantan

  DOI：10.1016/j.saa.2012.11.100

  日期：2013.3

  Salen [2,2'-propane-1,3-diylbis[nitrilo(E)methylylidene]}bis(6-methoxyphenol)], reduced salen [(2,2'-[propane-1,3-diylbis(iminomethylene))]bis(6-methoxyphenol)] and N-alkylated salen [diethyl-2,2'-(propane-1,3-diylbis((2-hydroxy-3-methoxybenzyl) azanediyl))diacetate] compounds have been synthesized and characterized by IR, H-1 NMR, C-13 NMR and UV-vis. spectroscopy. Molecular geometry of the title compounds in the ground state has been optimized by density functional method (B3LYP) with 6-31G basis set. Vibrational frequencies of the compounds were computed and compared with the experimental values. Tautomeric stability study of salen inferred that the enolimine form is more stable than its keto-enamine form in gas phase. The spectral behavior of salen in polar and nonpolar solvents was examined demonstrate the positive solvatochromism. The synthesized compounds have been studied with respect to their binding to calf thymus DNA showed that there were interactions between the compounds and DNA through a groove binding mode. Furthermore, the DNA cleavage activity of the compounds has been investigated by gel electrophoresis. The antioxidant properties of compounds were evaluated by DPPH method. The N-alkylated compound has a higher DPPH free radical scavenging activity. The antimicrobial activity was investigated on various gram positive and gram negative bacteria. (C) 2012 Elsevier B.V. All rights reserved.