N-(2-hydroxy-5-methylphenyl)-N′-[2-(dimethylamino)ethyl]oxamide

• 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-(2-hydroxy-5-methylphenyl)-N′-[2-(dimethylamino)ethyl]oxamide
• 英文别名: N-[2-(dimethylamino)ethyl]-N'-(2-hydroxy-5-methylphenyl)oxamide
• 化学式: C₁₃H₁₉N₃O₃
• 分子量: 265.312
• InChiKey: NWSFSOIIJWUCED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-二甲基-2,2'-联吡啶 、 copper(II) perchlorate hexahydrate 、 N-(2-hydroxy-5-methylphenyl)-N′-[2-(dimethylamino)ethyl]oxamide 在 哌啶 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以75%的产率得到[Cu₂(hmdoxd)(H₂O)(4,4′-dimethyl-2,2′-bipyridine)](ClO₄)*DMF
  参考文献：
  名称：

  Synthesis and structure elucidation of new μ-oxamido-bridged dicopper(II) complexes showing in vitro anticancer activity: Evaluation of DNA/protein-binding properties by experiment and molecular docking

  摘要：

  Two new mu-oxamido-bridged dicopper(II) complexes formulated as [Cu-2(hmdoxd)(H2O)(Me(2)bPY)]-(ClO4)center dot DMF (1) and [Cu-2(hmdoxd)(bpy)](ClO4)center dot CH3OH (2), where H(3)hmdoxd is N-(2-hydroxy-5-methylphenyl)-N'-[2-(dimethylamino)ethyl]oxamide; Me(2)bpy and bpy stand for 4,4'-dimethyl-2,2'-bipyridine and 2,2'-bipyridine, respectively, were synthesized and structurally characterized. The single-crystal X-ray diffraction analysis reveals that the copper(II) ions in complexes 1 and 2 are bridged by the cis-hmdoxd(3-) with corresponding Cu center dot center dot center dot Cu separations of 5.1596(6) and 5.1562(6) angstrom, respectively, in which the endo- and exo-copper(II) ions are located in square-planar and square-pyramidal geometries, respectively, for 1, and square-planar environments for 2. In the crystals of the two complexes, there are abundant hydrogen bonds and pi-pi stacking interactions contributing to the supramolecular structure. The DNA/protein-binding property of the two complexes are studied both theoretically and experimentally, indicating that complexes 1 and 2 can interact with DNA in the mode of intercalation and partial intercalation, respectively, and effectively bind to protein BSA via the favored binding sites Trp213 for 1 and Trp134 for 2. In vitro anticancer activities showed that the two complexes are active against the selected tumor cell lines, and the anticancer activities are consistent with their DNA/protein-binding affinities following the order of 1 > 2. The effect of the hydrophobicity of both the bridging and terminal ligands in the dicopper(II) complexes on DNA/protein-binding events and in vitro anticancer activities is preliminarily discussed. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2015.12.023

文献信息

• Synthesis and structure elucidation of new μ-oxamido-bridged dicopper(II) complexes showing in vitro anticancer activity: Evaluation of DNA/protein-binding properties by experiment and molecular docking
  作者：Kang Zheng、Fang Liu、Yan-Tuan Li、Zhi-Yong Wu、Cui-Wei Yan

  DOI：10.1016/j.jinorgbio.2015.12.023

  日期：2016.3

  Two new mu-oxamido-bridged dicopper(II) complexes formulated as [Cu-2(hmdoxd)(H2O)(Me(2)bPY)]-(ClO4)center dot DMF (1) and [Cu-2(hmdoxd)(bpy)](ClO4)center dot CH3OH (2), where H(3)hmdoxd is N-(2-hydroxy-5-methylphenyl)-N'-[2-(dimethylamino)ethyl]oxamide; Me(2)bpy and bpy stand for 4,4'-dimethyl-2,2'-bipyridine and 2,2'-bipyridine, respectively, were synthesized and structurally characterized. The single-crystal X-ray diffraction analysis reveals that the copper(II) ions in complexes 1 and 2 are bridged by the cis-hmdoxd(3-) with corresponding Cu center dot center dot center dot Cu separations of 5.1596(6) and 5.1562(6) angstrom, respectively, in which the endo- and exo-copper(II) ions are located in square-planar and square-pyramidal geometries, respectively, for 1, and square-planar environments for 2. In the crystals of the two complexes, there are abundant hydrogen bonds and pi-pi stacking interactions contributing to the supramolecular structure. The DNA/protein-binding property of the two complexes are studied both theoretically and experimentally, indicating that complexes 1 and 2 can interact with DNA in the mode of intercalation and partial intercalation, respectively, and effectively bind to protein BSA via the favored binding sites Trp213 for 1 and Trp134 for 2. In vitro anticancer activities showed that the two complexes are active against the selected tumor cell lines, and the anticancer activities are consistent with their DNA/protein-binding affinities following the order of 1 > 2. The effect of the hydrophobicity of both the bridging and terminal ligands in the dicopper(II) complexes on DNA/protein-binding events and in vitro anticancer activities is preliminarily discussed. (C) 2015 Elsevier Inc. All rights reserved.