N-{[4-(1,3-benzothiazol-2-yl)anilino]carbonylmethyl}iminodiacetic acid | 1156005-43-4

• 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-{[4-(1,3-benzothiazol-2-yl)anilino]carbonylmethyl}iminodiacetic acid
• 英文别名: (N-(4-benzothiazol-2-ylphenyl)carbamoylmethyl)iminodiacetic acid；(2-(4-(benzothiazole)phenyl)carbamoylmethyl)iminodiaceticacid；2-[[2-[4-(1,3-Benzothiazol-2-yl)anilino]-2-oxoethyl]-(carboxymethyl)amino]acetic acid
• CAS: 1156005-43-4
• 化学式: C₁₉H₁₇N₃O₅S
• 分子量: 399.427
• InChiKey: GYEYKYPXVBBYEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,10-菲罗啉 、 N-{[4-(1,3-benzothiazol-2-yl)anilino]carbonylmethyl}iminodiacetic acid 、 cobalt(II) chloride hexahydrate 以 N,N-二甲基甲酰胺 为溶剂， 生成 (N-[[4-(1,3-benzothiazol-2-yl)anilino]carbonylmethyl-κO]iminodiacetato-κ(3)O,N,O')(1,10-phenanthroline-κ(2)N,N')cobalt(II) pentahydrate
  参考文献：
  名称：

  (N-{[4-(1,3-Benzothiazol-2-yl)anilino]carbonylmethyl-κO}iminodiacetato-κ³O,N,O′)(1,10-phenanthroline-κ²N,N′)cobalt(II) pentahydrate

  摘要：

  The title compound, [Co(C(19)H(15)N(3)O(5)S)(C(12)H(8)N(2))] x 5 H(2)O, has a moderately distorted octahedral coordination environment composed of two N atoms of a 1,10-phenanthroline ligand and one N and three O atoms of an N-{[4-(1,3-benzothiazol-2-yl)anilino]carbonylmethyl}iminodiacetate (ZL-5(2-)) ligand. The ring systems of the phenanthroline and ZL-5(2-) ligands are coplanar and the complexes pack in layers parallel to the ab plane with the rings of adjacent complexes facing one another. The layers stack along the c axis and are linked by hydrogen bonds involving the five water solvent molecules in the asymmetric unit and O atoms of the acetate groups of the ZL-5(2-) ligand. This is believed to be the first crystal structure of a complex of a 2-(4-aminophenyl)benzothiazole ligand.

  DOI：

  10.1107/s0108270108006306
• 作为产物：
  描述：

  4-(2-苯并噻唑基)苯胺 在 盐酸 、 sodium carbonate 、 三乙胺 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 14.0h， 生成 N-{[4-(1,3-benzothiazol-2-yl)anilino]carbonylmethyl}iminodiacetic acid
  参考文献：
  名称：

  Synthesis, structures and the biological activity study on the metal complexes of 2-(4-aminophenyl)benzothiazole derivative

  摘要：

  (2-(4-(苯并噻二唑基)苯基)羰基甲基)乙二胺四乙酸(ZL-5)被合成,然后制备了它的三种金属配合物,并用H-1 NMR或X射线确定其结构。在所有配合物中,ZL-5脱质子生成中性配合物单元,并作为四齿配体,提供乙二胺四乙酸的N原子和三个O原子与金属离子结合。同时,我们通过紫外光谱和荧光光谱研究了配合物与DNA的相互作用。此外,我们还通过凝胶电泳研究了配合物对质粒pBR 322 DNA的切割能力。我们推断,具有最大平面结构的Co(II)配合物1主要通过嵌入模式具有最强的DNA结合能力,而具有配位水的Cu(II)配合物2最有效地切割DNA。在所有配合物的氧化切开过程中,会生成羟基自由基,其可被DMSO捕捉。©2011 Elsevier B.V. 保留所有权利。

  DOI：

  10.1016/j.ica.2011.10.004

文献信息

• Synthesis, structures and the biological activity study on the metal complexes of 2-(4-aminophenyl)benzothiazole derivative
  作者：Guo-Wu Lin、Yue Wang、Qiao-Mei Jin、Tao-Tao Yang、Jie-Mei Song、Yi Lu、Qing-Jie Huang、Ke Song、Jun Zhou、Tao Lu

  DOI：10.1016/j.ica.2011.10.004

  日期：2012.3

  (2-(4-(Benzothiazole)phenyl)carbamoylmethyl) iminodiacetic acid (ZL-5) was synthesized and then its three metal complexes were prepared with structures determined by H-1 NMR or X-ray. In all complexes, ZL-5 is deprotonated to generate the neutral complex unit and acts as a tetradentate ligand, providing iminodiacetic N atom and three O atoms to bond with metal ions. Meantime we studied on the interaction of complexes with DNA by ultraviolet spectrum and fluorescent spectrum. Also the cleavage abilities of the complexes on plasmid pBR 322 DNA were studied by gel electrophoresis. We deduce the Co(II) complex 1 with the largest planar structure has the strongest DNA binding ability mainly by the intercalation mode, while the Cu(II) complex 2 with the coordinated water cut the DNA most effectively. And in the oxidative cleavage process of all complexes, the hydroxyl radical is produced which can be captured by DMSO. (C) 2011 Elsevier B. V. All rights reserved.

  (2-(4-(苯并噻二唑基)苯基)羰基甲基)乙二胺四乙酸(ZL-5)被合成,然后制备了它的三种金属配合物,并用H-1 NMR或X射线确定其结构。在所有配合物中,ZL-5脱质子生成中性配合物单元,并作为四齿配体,提供乙二胺四乙酸的N原子和三个O原子与金属离子结合。同时,我们通过紫外光谱和荧光光谱研究了配合物与DNA的相互作用。此外,我们还通过凝胶电泳研究了配合物对质粒pBR 322 DNA的切割能力。我们推断,具有最大平面结构的Co(II)配合物1主要通过嵌入模式具有最强的DNA结合能力,而具有配位水的Cu(II)配合物2最有效地切割DNA。在所有配合物的氧化切开过程中,会生成羟基自由基,其可被DMSO捕捉。©2011 Elsevier B.V. 保留所有权利。
• (<i>N</i>-{[4-(1,3-Benzothiazol-2-yl)anilino]carbonylmethyl-κ<i>O</i>}iminodiacetato-κ³<i>O</i>,<i>N</i>,<i>O</i>′)(1,10-phenanthroline-κ²<i>N</i>,<i>N</i>′)cobalt(II) pentahydrate
  作者：Guo-Wu Lin、Yue Wang、Tao Lu

  DOI：10.1107/s0108270108006306

  日期：2008.4.15

  The title compound, [Co(C(19)H(15)N(3)O(5)S)(C(12)H(8)N(2))] x 5 H(2)O, has a moderately distorted octahedral coordination environment composed of two N atoms of a 1,10-phenanthroline ligand and one N and three O atoms of an N-[4-(1,3-benzothiazol-2-yl)anilino]carbonylmethyl}iminodiacetate (ZL-5(2-)) ligand. The ring systems of the phenanthroline and ZL-5(2-) ligands are coplanar and the complexes pack in layers parallel to the ab plane with the rings of adjacent complexes facing one another. The layers stack along the c axis and are linked by hydrogen bonds involving the five water solvent molecules in the asymmetric unit and O atoms of the acetate groups of the ZL-5(2-) ligand. This is believed to be the first crystal structure of a complex of a 2-(4-aminophenyl)benzothiazole ligand.