N-(5-chloro-2-hydroxyphenyl)-N'-[3-(dimethylamino)propyl]oxalamide | 1219572-11-8

• 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-(5-chloro-2-hydroxyphenyl)-N'-[3-(dimethylamino)propyl]oxalamide
• 英文别名: N-(5-chloro-2-hydroxyphenyl)-N'-[3-(dimethylamino)propyl]oxamide；H3chdpoxd；N-(5-chloro-2-hydroxyphenyl)-N'-[3-(dimethylamino)propyl]ethanediamide；N'-(5-chloro-2-hydroxyphenyl)-N-[3-(dimethylamino)propyl]oxamide
• CAS: 1219572-11-8
• 化学式: C₁₃H₁₈ClN₃O₃
• 分子量: 299.757
• InChiKey: JVRXXYOJMOWFNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  5
• 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：

  copper(II) perchlorate hexahydrate 、 N-(5-chloro-2-hydroxyphenyl)-N'-[3-(dimethylamino)propyl]oxalamide 在 哌啶 作用下， 以 甲醇 为溶剂， 以31%的产率得到
  参考文献：
  名称：

  N-（5-氯-2-羟苯基）-N'-[3-（二甲基氨基）丙基]乙酰胺桥接的新三金属配合物的合成和结构：细胞毒活性以及对DNA和蛋白质的反应性。

  摘要：

  两个新的μ-乙酰胺基桥联的三核复合物，即[Cu（3）L（2）（H（2）O）（2）] {[Cu（3）L（2）]·2H（2）O}（ 2）（1）和[Ni（3）L（2）（H（2）O）（DMF）]（H（2）O）（DMF）（2），其中L（3-）是去质子化的N- （5-氯-2-羟基苯基）-N’-[3-（二甲基氨基）丙基]乙酰胺已经合成并通过X射线单晶衍射表征。配合物1的结构由三个tricopper（II）中性分子组成，位于Cu5原子的反转中心，因此具有反式构象。配合物2的结构由三镍（II）中性分子组成。研究了体外细胞毒性活性，以及​​两种复合物对DNA和蛋白质的反应性。细胞毒性实验表明，这两种三核复合物均对人肝癌细胞SMMC-7721和人肺腺癌细胞A549均具有细胞毒性作用。使用紫外吸收和荧光光谱以及粘度测定法研究了两种复合物与鲱鱼精子DNA（HS-DNA）的相互作用。结果表明，两种三核复合物均可以通过

  DOI：

  10.1016/j.jphotobiol.2012.10.009
• 作为产物：
  描述：

  Ethyl 5-chloro-2-hydroxyoxanilate 、 N,N-二甲基-1,3-二氨基丙烷 以 乙醇 为溶剂， 反应 2.0h， 生成 N-(5-chloro-2-hydroxyphenyl)-N'-[3-(dimethylamino)propyl]oxalamide
  参考文献：
  名称：

  Bimetallic complexes constructed from asymmetrical N,N′-bis(substituted)-oxamide: Cytotoxicities, and reactivities towards DNA and protein

  摘要：

  A new asymmetrical N,N'-bis(substituted)oxamide ligand, N-(5-chloro-2-hydroxyphenyl)-N'-(3-(dimethylamino)propyl]oxamide (C13E18N3O3Cl center dot H2O, H3L) and its two binuclear complexes [Cu2L (H2O)(bpy)](ClO4)center dot CH3OH (1) and [Ni2L(bPY)(2)](ClO4) (2) [bpy = 2.2'-bipyridine] have been synthesized and characterized by X-ray single-crystal diffraction. In the crystal structure, H3L adopting a transoid conformation occurs as a neutral molecule linked with a water molecule by an intermolecular hydrogen bond. In the two complexes, the cis-L3- ligand bridges two metal ions with the corresponding separations of 5.2032(15) angstrom (1) and 5.2466(7) angstrom (2), respectively. In vitro cytotoxic activities, and the reactivities of the three compounds towards DNA and protein are investigated. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.022

文献信息

• Synthesis and structures of binuclear copper(II) complexes bridged by N-(5-chloro-2-hydroxyphenyl)-N′-[3-(dimethylamino)propyl]oxalamide ligand: DNA-binding properties and cytotoxic activities
  作者：Xiao-Wen Li、Xin Li、Yan-Tuan Li、Zhi-Yong Wu、Cui-Wei Yan

  DOI：10.1016/j.jorganchem.2011.11.013

  日期：2012.3

  X-ray diffraction. In both complexes 1 and 2, the cis-chdpoxd3− ligand bridges two copper(II) ions with the corresponding separations of 5.2003(5) and 5.1664(17) Å, respectively, and the polyhedron of Cu1 is a distorted square-planar, of Cu2 is a square-pyramidal. Through π–π stacking and hydrogen bonding interactions, the two bicopper(II) complexes are assembled to 3D supramolecular structures, which are

  N-（5-氯-2-羟基苯基）-N '-[3-（二甲氨基）丙基]草酰胺（H 3 chdpoxd）桥接的两个新的双核铜（II）络合物，并用1,10-菲咯啉封端分子式分别为[Cu 2（chdpoxd）（H 2 O）（phen）]（NO 3）·H 2 O（1）的（phen）或5-硝基-1,10-菲咯啉（NO 2 phen）。并通过单晶X射线衍射合成了[Cu 2（chdpoxd）（CH 3 CH 2 OH）（NO 2 phen）]（NO 3）（2）并对其进行了表征。在两个复合体中1和2，顺式-chdpoxd 3-配体桥接两个铜离子，相应的间隔分别为5.2003（5）和5.1664（17）Å，Cu1的多面体为扭曲的方平面，Cu2为方形金字塔形。通过π-π堆积和氢键相互作用，两个bicopper（II）配合物组装成3D超分子结构，由于末端配体上的取代基，它们彼此不同。磺胺多巴胺B（SRB）分析测试的两种
• Syntheses and structures of bicopper(II) complexes bridged by N-(5-chloro-2-hydroxyphenyl)-N′-[3-(dimethylamino)propyl]oxamide: Cytotoxic activities, and reactivities towards DNA and protein
  作者：Xiao-Wen Li、Yan-Tuan Li、Zhi-Yong Wu、Cui-Wei Yan

  DOI：10.1016/j.ica.2012.04.032

  日期：2012.7

  Two new binuclear copper(II) complexes bridged by N-(5-chloro-2-hydroxyphenyl)-N'-[3-(dimethylamino) propyl] oxamide (H3L), and end-capped with 4,4'-dimethyl-2,2'-bipyridine (Me(2)bpy) or 2,2'-diamino-4,4'-bithiazole (dabt), respectively, namely [Cu2L(H2O)(Me(2)bpy)][Cu2L(CH3OH)(Me(2)bpy)] (ClO4)(2)(CH3OH)(0.7) (1) and [Cu2L(CH3OH)(0.25)(dabt)]ClO4 center dot(H2O)(1.5) (2), have been synthesized and characterized by single-crystal X-ray diffraction. In complex 1, the dissymmetric unit of it contains two bicopper(II) cations, the cis-L-3 ligands bridge two copper(II) ions with the corresponding separations of 5.1881(11) angstrom (Cu1 center dot center dot center dot Cu2) and 5.2193(11) angstrom (Cu3 center dot center dot center dot Cu4), respectively. In complex 2, the L-3 ligand is adopting a cis conformation with the Cu center dot center dot center dot Cu distance of 5.2409 (7) angstrom. Through pi-pi stacking and hydrogen bonding interactions, the two bicopper(II) complexes are assembled to 3D supramolecular structures. Cytotoxic activities, and the reactivities towards DNA and protein of the two bicopper(II) complexes are investigated. The results suggest that the two bicopper(II) complexes interact with HS-DNA in the mode of intercalation, and the DNA-binding abilities are consistent with cytotoxic activities following the order of 2 > 1. The protein binding ability has been monitored using bovine serum albumin (BSA) as model protein. (C) 2012 Elsevier B. V. All rights reserved.